CN117062914A - 方法和组合物 - Google Patents
方法和组合物 Download PDFInfo
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- CN117062914A CN117062914A CN202180087397.0A CN202180087397A CN117062914A CN 117062914 A CN117062914 A CN 117062914A CN 202180087397 A CN202180087397 A CN 202180087397A CN 117062914 A CN117062914 A CN 117062914A
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Abstract
本发明涉及QS‑21分子的中间体的生物合成途径以及制备QS‑21分子的途径、所涉及的酶、所产生的产物和所述产物的用途。
Description
技术领域
本发明涉及QS-21分子的中间体的生物合成途径，以及制备QS-21分子的途径、所涉及的酶、所产生的产物和产物的用途。
背景技术
QS-21是从智利“皂树(soapbark)”(Quillaja saponaria)的树皮提取的天然皂苷。QS-21提取物最初被鉴定为通过RP-HPLC纯化所获得的皂树(Quillaja SaponariaMolina)的树皮粗提取物的纯化部分(峰21)(Kensil等人1991)。QS-21提取物或级分包含一些不同的皂苷分子。报道了所述部分的两种主要异构分子成分(Ragupathi等人2011)并且如图1所示。两者均引入了中央三萜核心，支链三糖在萜烯C-3氧官能性处连接至所述中央三萜核心，并且直链四糖连接至三萜C-28羧化酶基团。皂苷结构内的第四组分是经由水解不稳定的酯键连接至岩藻糖部分的糖基化的伪二聚酰基链。所述异构组分在四糖的末端糖残基的组成方面不同，其中主要和次要化合物分别引入了芹菜糖(65％)或木糖(35％)碳水化合物。
常年已知来自皂树(Q.saponaria)的包括QS-21的皂苷具有有效的免疫刺激性质，能够增强抗体产生和特异性T细胞应答。这些性质导致了用于疫苗的基于皂树皂苷的佐剂的开发。特别注意，AS01佐剂是QS-21和3-O-去酰基-4'-单磷酰脂质A的脂质体制剂(WO2013/041572中描述了它的产生)并且目前许可在用于疾病(包括带状疱疹(Shingrix)和疟疾(Mosquirix))的疫苗制剂中使用。
本发明描述了除通过从天然皂树(Q.saponaria)植物纯化外合成QS-21分子中间体以及QS-21分子的方法以及所得产物，其作为疫苗制剂中的佐剂是有用的。本发明还涉及产生所述产物的参与所述方法的酶、载体、宿主细胞和生物系统。
发明内容
本发明具体地涉及将C-28直链四糖生物合成添加至包含皂皮酸主链(QA)的分子中以及所产生的QA衍生物。本发明包括QS-21分子的中间体，如(例如)QA-FRX(X/A)或QA-Tri(X/R)-FRX(X/A)的生物合成制备，以及制备QS-21分子的化学途径，制备衍生物和分子的所有组成部分，及其用途。
QA生物合成衍生自简单的三萜β-香树素，QA通过经由氧化鲨烯环化酶(OSC)的通用直链前体2,3-氧化鲨烯(OS)的环化作用合成。这种生物合成在本领域中是已知的，如WO2019/122259，以上专利的内容作为参考并入。这种β-香树素骨架通过一系列三种细胞色素P450单加氧酶，被羧酸、醇和醛分别在C-28位、C-16α位和C-23位进一步氧化，从而形成皂皮酸(QA)。OSC和C-28氧化酶、C16α氧化酶和C-23氧化酶在本文中分别被称为QsbAS(β-香树素合酶)、QsCYP716-C-28氧化酶、QsCYP716-C-16α氧化酶和QsCYP714-C-23氧化酶。图2提供了其生物合成途径。
通过经由β-键在QA主链的C-3位连接的D-吡喃葡糖醛酸(D-GlcpA)残基起始QS-21中的支链三糖链。D-GlcpA残基具有与之连接的两种糖：通过β-1,2-键连接的D-吡喃半乳糖(D-Galp)和分别通过β-1,3-键或α-1,3-键连接的D-吡喃木糖(D-Xylp)或L-吡喃鼠李糖(L-Rhap)。图3显示了QA糖基化为3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-皂皮酸(QA-TriR)或者3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-皂皮酸(QA-TriX)的示意图。已鉴定了具有与QA3-O三糖生产有关的活性的七种酶，如PCT/EP2020/067866中(作为WO2020/260475公开)。这些包括两种功能冗余的萄糖醛酸转移酶，CSL1和CslG2，其可以在皂皮酸的C-3位添加初始的β-D-吡喃葡糖醛酸；半乳糖基转移酶，Qs-3-O-GalT，其向β-D-吡喃葡糖醛酸的C-2位添加β-D-吡喃半乳糖；木糖基转移酶，Qs_0283870，其向β-D-吡喃葡糖醛酸的C-3位添加β-D-吡喃木糖；两种鼠李糖基转移酶，DN20529_c0_g2_i8和Qs_0283850，其向β-D-吡喃葡糖醛酸的C-3位添加α-L-吡喃鼠李糖；和双功能酶，Qs-3-O-RhaT/XylT，其可以向β-D-吡喃葡糖醛酸的C-3位添加β-D-吡喃木糖或α-L-吡喃鼠李糖(图3)。为简单起见，在本发明申请中，在C-3位包括支链三糖的QA衍生物可以表示为“QA-TriX”、“QA-TriR”或者“QA-Tri(X/R)”。
除通过从天然皂树(Q.saponaria)植物纯化外，本发明首次描述了在QA主链的C-28位添加直链四糖的生物合成途径以及所得衍生物，如(例如)QA-FRX(X/A)或QA-Tri(X/R)-FRX(X/A)，包括化学产生QS-21分子的那些。
因此，本发明提供了制备QA衍生物的方法，由此能够获得的QA衍生物、在所述方法中使用的酶、编码所述酶的核酸、包含所述核酸的载体、用所述载体转化的宿主细胞。
附图说明
图1显示了QS-21的结构。核心主链由三萜皂皮酸(QA)形成。C-3位具有由β-D-吡喃葡糖醛酸(D-GlcpA)、β-D-吡喃半乳糖(D-Galp)和位于(R1)的β-D-吡喃木糖(D-xylp)或α-L-吡喃鼠李糖(L-rhap)组成的支链三糖。C-28位具有由β-D-吡喃岩藻糖(D-fucp)、α-L-吡喃鼠李糖、β-D-吡喃木糖和位于(R2)的末端β-D-呋喃芹菜糖(D-apif)或β-D-吡喃木糖组成的直链四糖。D-岩藻糖还具有通过α-L-呋喃阿拉伯糖(L-Araf)封端的18-碳酰基链。图2显示了碳编号。
图2显示了从2,3-氧化鲨烯经由β-香树素生产皂皮酸(QA)。图2中标记了本文所提及的重要的β-香树素碳的编号。来自β-香树素的途径需要在3个位置(C-28、C-23和C-16α)氧化。为简单起见，以直链方式显示了这些氧化步骤；然而，它们可以以任何顺序发生。
图3显示了从皂皮酸(QA)生产QA-TriR或QA-TriX。通过萄糖醛酸转移酶QsCLS1或QsCslG2中的任一个将β-D-吡喃葡糖醛酸(β-D-GlcpA)添加至皂皮酸的C-3位以形成QA-Mono。半乳糖基转移酶Qs-3-O-GalT将β-D-吡喃半乳糖(β-D-Galp)添加至吡喃葡糖醛酸的C-2位以形成QA-Di。通过单功能鼠李糖基转移酶DN20529_c0_g2_i8或Qs_0283850，或者通过双功能Qs-3-O-RhaT/XylT，可以将α-L-吡喃鼠李糖(α-L-Rhap)连接至吡喃葡糖醛酸的C-3位以形成QA-TriR。作为另外一种选择，可以通过单功能木糖基转移酶Qs_0283870或者通过双功能Qs-3-O-RhaT/XylT将β-D-吡喃木糖(β-D-Xylp)连接至吡喃葡糖醛酸的C-3位以形成QA-TriX。
图4显示了所提议的从QA-Tri(X/R)生物合成QS-21C-28直链四糖链。通过经由酯键将β-D-吡喃岩藻糖(β-D-Fucp)连接至皂皮酸的C-28来起始链，然后连接α-1,2-L-吡喃鼠李糖(α-L-Rhap)和连接β-1,4-D-吡喃木糖(β-D-Xylp)。所述链的末端糖可以是β-1,3-D-吡喃木糖(β-D-Xylp)或者β-1,3-D-呋喃芹菜糖(β-D-Apif)。为简单起见，所得QA衍生物可以表示为“QA-Tri(X/R)-FRX(X/A)”。
图5显示了三萜C-28岩藻糖基转移酶(Qs-28-O-FucT)的鉴定。通过HPLC-CAD-MS分析了瞬时表达皂树(Q.saponaria)基因的本氏烟草(N.benthamiana)的叶提取物。显示了HPLC-CAD迹线(顶部)和所提取的离子色谱图(EIC)(底部)。生产QA-Tri(X/R)所需的基因(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCSL1+Qs-3-O-GalT+Qs-3-O-RhaT/XylT)的共表达获得了QA-TriR(12.6分钟，m/z＝969)和QA-TriX(12.8分钟，m/z＝955)的两个重叠峰。QsUGT_L2的进一步共表达导致在11.6和12.3分钟之间积累了新的更极性的峰，其具有与将戊糖添加至QA-TriR和QA-TriX以分别形成QA-TriR-F(MW＝1116.54)和QA-TriX-F(MW＝1102.52)一致的质量离子(m/z＝1115和1101)。IS，内标(洋地黄毒苷)。
图6显示了三萜C-28鼠李糖基转移酶(Qs-28-O-RhaT)的鉴定。通过HPLC-CAD-MS分析了瞬时表达皂树(Q.saponaria)基因的本氏烟草(N.benthamiana)的叶提取物。显示了HPLC-CAD迹线(顶部)和所提取的离子色谱图(EIC)(底部)。生产QA-TriX所需的基因(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCSL1+Qs-3-O-GalT+Qs_0283870)与Qs-28-O-FucT(即QsUGT_L2)的共表达获得了QA-TriX的峰(12.8分钟，m/z＝955)和QA-TriX-F的峰(12.0分钟，m/z＝1101)。QsUGT_A6的进一步共表达导致QA-TriX-F峰减小以及在11.6分钟的更极性的峰的积累，其质量离子(m/z＝1247)与将鼠李糖添加至QA-TriX-F以形成QA-TriX-FR(MW＝1248.58)一致。QsUGT_A6的进一步共表达且不共表达Qs-28-O-FucT(即QsUGT_L2)导致仅前体QA-TriX的积累。IS，内标(洋地黄毒苷)。
图7显示了三萜C-28木糖基转移酶(Qs-28-O-XylT3)的鉴定。通过HPLC-CAD-MS分析了瞬时表达皂树(Q.saponaria)基因的本氏烟草(N.benthamiana)的叶提取物。显示了HPLC-CAD迹线(顶部)和所选的提取的离子色谱图(EIC)(底部)。生产QA-TriX-F所需的基因(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCSL1+Qs-3-O-GalT+Qs_0283870+Qs-28-O-FucT[即QsUGT_L2])的共表达获得了QA-TriX的峰(12.8分钟，m/z＝955)和QA-TriX-F的峰(12.0分钟，m/z＝1101)。Qs-28-O-RhaT(即QsUGT_A6)的进一步共表达导致QA-TriX-FR(11.6分钟)的积累。QsUGT_A7的进一步共表达导致QA-TriX-FR和QA-TriX峰减小以及在11.9分钟的峰的积累，其质量(m/z＝1379)与将木糖添加至QA-TriX-FR以形成QA-TriX-FRX(MW＝1380.62)一致。QsUGT_A7的进一步共表达且不共表达Qs-28-O-RhaT(即QsUGT_A6)导致QA-TriX和QA-TriX-F的积累。IS，内标(洋地黄毒苷)。
图8显示了三萜C-28葡萄糖基转移酶的鉴定。通过HPLC-CAD-MS分析了瞬时表达皂树(Q.saponaria)和积雪草(Centella asiatica)基因的本氏烟草(N.benthamiana)的叶提取物。显示了HPLC-CAD迹线(顶部)和所提议的途径(底部)。生产QA-TriX所需的基因(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283870)的共表达获得了QA-TriX峰(12.8分钟，m/z＝955)。C-28葡萄糖基转移酶CaUGT73AD1(de Costa等人,2017)的进一步共表达导致位于10.1分钟处的峰(m/z＝1117)的积累，其质量与将葡萄糖(Glcp)添加至QA-TriX以形成QA-TriX-G一致，并且产生了位于11.8分钟处的另外的新的峰(m/z＝1101)，其与葡萄糖向Gyp-TriX(缺少通过QsCYP716-C-16α的C-16氧化的中间体)的添加一致。Qs-28-O-RhaT的进一步共表达导致QA-TriX-G和Gyp-TriX-G峰的减少以及位于9.5分钟(m/z＝1263)和11.1分钟(m/z＝1247)处的两个更极性的峰的积累，两者质量与鼠李糖(Rhap)向QA-TriX-G和Gyp-TriX-G添加以分别形成QA-TriX-GR(MW＝1264.57)和Gyp-TriX-GR(MW＝1248.58)一致。Qs-28-O-XylT3的进一步共表达导致9.5分钟和11.1分钟处的峰减小以及位于9.8分钟(m/z＝1395)和11.5分钟(m/z＝1379)的两个新的峰的积累，两者的质量离子与木糖(Xylp)向QA-TriX-GR和Gyp-TriX-GR添加以分别形成QA-TriX-GRX(MW＝1396.61)和Gyp-TriX-GRX(MW＝1380.62)一致。IS，内标(洋地黄毒苷)。
图9显示了三萜C-28木糖基/芹菜糖基转移酶的鉴定。通过HPLC-CAD-MS分析了瞬时表达皂树(Q.saponaria)和积雪草(Centella asiatica)基因的本氏烟草(N.benthamiana)的叶提取物。生产QA-TriX-GRX所需的基因(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283870+CaUGT73AD1+Qs-28-O-RhaT+Qs-28-O-XylT3)的共表达获得了QA-TriX的峰(12.8分钟，m/z＝955)、QA-TriX-GRX的峰(9.5分钟，m/z＝1395)和Gyp-TriX-GRX的峰(11.2分钟，m/z＝1379)。QsAXS1的进一步共表达未改变这些峰的积累。QsAXS1与QsUGT_D3的进一步共表达导致QA-TriX-GRX和Gyp-TriX-GRX峰减小以及位于9.6分钟(m/z＝1528)和11.5分钟(m/z＝1512)的峰的积累。QsAXS1与两个候选QsUGT_D2和QsUGT_A3的进一步共表达也导致QA-TriX-GRX和Gyp-TriX-GRX峰减小以及位于9.7分钟(m/z＝1528)和11.6分钟(m/z＝1512)的峰的积累。IS，内标(洋地黄毒苷)。
图10显示QsUGT_D2的活性取决于QsAXS1。通过HPLC-CAD-MS分析了瞬时表达皂树(Q.saponaria)和积雪草(Centella asiatica)基因的本氏烟草(N.benthamiana)的叶提取物。显示了所提取的离子色谱图。生产QA-TriX-GRX所需的基因(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283870+CaUGT73AD1+Qs-28-O-RhaT+Qs-28-O-XylT3)与单独的QsUGT_D3的共表达导致位于12.8分钟的QA-TriX的峰(m/z＝955)以及位于9.6分钟(m/z＝1528)和11.5分钟(m/z＝1512)的两个峰的积累，这两个峰的质量离子分别与QA-TriX-GRX(X/A)(MW＝1528.66)和Gyp-TriX-GRX(X/A)(MW＝1512.66)一致。单独的QsUGT_D2与生产QA-TriX-GRX所需的基因的共表达产生了位于12.8分钟的QA-TriX(m/z＝955)、QA-TriX-GRX(9.5分钟，m/z＝1395)、Gyp-TriX-GRX(11.2分钟，m/z＝1379)的峰，并且导致位于9.7分钟(m/z＝1528)和11.6分钟(m/z＝1512)的峰仅痕量积累。QsUGT_D2以及QsAXS1的添加导致QA-TriX-GRX和Gyp-TriX-GRX峰减小较大，并且导致位于9.7分钟的峰(m/z＝1528)和11.6分钟的峰(m/z＝1512)的积累升高。这些后面的峰分别与QA-TriX-GRX(X/A)(MW＝1528.66)和Gyp-TriX-GRX(X/A)(MW＝1512.66)的积累一致。IS，内标(洋地黄毒苷)。
图11显示了本氏烟草(N.benthamiana)中UDP-α-D-岩藻糖的生产。进行本氏烟草(N.benthamiana)植物的糖核苷酸分析，并且显示UDP-脱氧-己糖的迹线。用水浸润的对照植物(顶部)仅显示单一峰，针对真实的标准品(标准品未显示)确认为UDP-β-L-鼠李糖。用50mM D-岩藻糖溶液浸润的植物(中间)显示出两个新的峰的积累(标记为1和2)。通过用UDP-α-D-岩藻糖的真实标准品对样品加标(底部)，峰1显示为UDP-α-D-岩藻糖。据信第二峰(2)为UDP-α-D-喹诺糖，其通过内源差向异构酶(如UDP-D-葡萄糖/UDP-D-半乳糖4-差向异构酶)从UDP-α-D-岩藻糖的C-4差向异构产生。
图12显示浸润D-岩藻糖增强D-岩藻糖基化的QA衍生物的生产。生产QA-TriX-F所需的酶(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCSL1+Qs-3-O-GalT+Qs_0283870+Qs-28-O-FucT)单独(顶部)或者与添加50mM D-岩藻糖的浸润缓冲液(底部)在本氏烟草(N.benthamiana)中瞬时共表达。通过LC-MS对提取物的分析显示D-岩藻糖的存在足以将QA-TriX-F的生产增强几倍。结果呈现为QA-TriX-F(m/z 1101，黑色)和内标洋地黄毒苷(甲酸酯加合物＝809，灰色)的提取离子色谱图。
图13显示了从NDP-D-葡萄糖生物合成NDP-D-岩藻糖。
图14显示NDP-D-岩藻糖生物合成酶的瞬时表达可以加强本氏烟草(N.benthamiana)的岩藻糖基化产物的水平。在本氏烟草(N.benthamiana)中进行生产QA-TriX-F化合物的酶(AstHMGR,QsbAS,QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283870+Qs-28-O-FucT)的瞬时表达。另外，将参与从多种非植物种生物合成NDP-D-岩藻糖的一系列酶与上述酶瞬时共表达以确定它们加强QA-TriX-F产物得率的能力。这些包括刺胞虫(Acanthocystis turfacea)小球藻病毒1UDP-D-葡萄糖4,6-脱水酶(ATCV-1)，或者3种来自伴放线放线杆菌(Aggregatibacteractinomycetemcomitans)(AaFCD)、喜温无氧芽孢杆菌(Anoxybacillus tepidamans)(AtFCD)或大肠杆菌(Echerichia coli)(EcFCD)的细菌4-酮还原酶(FCD)。还进行了对照样品，包括添加50mM D-岩藻糖(阳性对照)，或者无岩藻糖-加强(仅QA-TriX-F酶)。通过LC-MS/CAD分析叶提取物，并且将结果显示为A)CAD色谱图或者B)MS提取离子色谱图(EIC)。选择QS-TriX-F产物(m/z 1101)和内标洋地黄毒苷(甲酸酯加合物＝809)的EIC质量。在表达NDP-D-岩藻糖生物合成酶(ATCV-1或者FCD酶)的任一种样品中，与未加强的对照相比，可以观察到QA-TriX-F产物明显升高。产物的量类似于阳性对照(+50mM D-岩藻糖)中存在的量。
图15显示与任一种酶单独的表达相比，ATCV-1和AaFCD的共表达对QA-TriX-F得率影响很小。在本氏烟草(N.benthamiana)中进行生产QA-TriX-F的酶的瞬时表达(AstHMGR、QsbAS、QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283870+Qs-28-O-FucT)。另外，还单独或一起共表达了刺胞虫小球藻病毒1UDP-D-葡萄糖4,6-脱水酶(ATCV-1)或者来自伴放线放线杆菌的4-酮还原酶(FCD)(AaFCD)。通过LC-MS分析叶提取物并且作为MS提取离子色谱图(EIC)显示结果。选择QS-TriX-F产物(m/z 1101)和内标洋地黄毒苷(甲酸酯加合物＝809)的EIC质量。与任一种酶单独的表达相比，ATCV-1和AaFCD两者的共表达造成了很小的差异。
图16显示通过皂树(Q.saponaria)氧化还原酶(FucSyn)的瞬时共表达增强了岩藻糖基化化合物的生产。顶部—在瞬时表达QA-TriR产物所必需的酶(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850—顶部色谱图)或QA-TriR-F产物所必需的酶(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850+Qs-28-O-FucT—第二色谱图)后本氏烟草(N.benthamiana)叶提取物的LC-CAD迹线。当成簇的氧化还原酶(FucSyn)与QA-TriR-F基因组共表达时，观察到11.5min处产物的大幅升高(底部色谱图)。当在不存在岩藻糖基转移酶Qs-28-O-FucT的情况下表达氧化还原酶时(第三色谱图)，不再观察到产物，从而表明氧化还原酶和岩藻糖基转移酶两者是位于11.5min的产物的高水平生产所必需的。底部—位于11.5min的这种化合物的质谱提供了m/z为1115的明显的离子。这与QA-TriR-F的预测分子量(MW＝1116.54)一致。
图17显示了本文所描述的不同加强策略的效力的比较。在本氏烟草(N.benthamiana)中瞬时共表达QA-TriR-F生产所必需的基因组(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850+Qs-28-O-FucT)。为了比较QA-TriR-F的相对量，用50mM D-岩藻糖、刺胞虫小球藻病毒1UDP-D-葡萄糖4,6-脱水酶(ATCV-1)或QsFucSyn酶共浸润QA-TriR-F酶组。结果显示为针对内标(洋地黄毒苷，16min)归一化的LC-CAD数据。在11.5min观察到QA-TriR-F，并且在表达QsFucSyn的样品中显示出最高的积累。
图18显示构建C-28糖苷和用QsFucSyn加强得率。通过相关基因组的瞬时表达，从QA-Tri-FR至QA-Tri-FRXA逐步构建QA-TriR分子的C-28四糖链(QA-TriR-FR—顶部(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850+Qs-28-O-FucT+Qs-28-O-RhaT—顶部)；QA-TriR-FRX—中间(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850+Qs-28-O-FucT+Qs-28-O-RhaT+Qs-28-O-XylT3)和QA-TriR-FRXA—底部(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850+Qs-28-O-FucT+Qs-28-O-RhaT+Qs-28-O-XylT3+Qs-28-O-ApiT4+QsAXS1)。在存在或不存在QsFucSyn酶的情况下，测试这些酶组中的每一种。结果表示为LC-CAD迹线(左图)。在每种情况下，在存在QsFucSyn的情况下观察到了相关产物的可见增加。产物相伴的质谱(右图)对应于预期产物的质量。
图19显示了具有不同末端糖变体的完整C-28四糖链的生产。在存在QsFucSyn酶的情况下表达生产QA-TriR-FRX所必需的酶组(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850+Qs-28-O-FucT+Qs-28-O-RhaT+Qs-28-O-XylT3—顶部)、生产QA-TriR-FRXX所必需的酶组(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850+Qs-28-O-FucT+Qs-28-O-RhaT+Qs-28-O-XylT3+Qs-28-O-XylT4—中间)和生产QA-TriR-FRXA所必需的酶组(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850+Qs-28-O-FucT+Qs-28-O-RhaT+Qs-28-O-XylT3+Qs-28-O-ApiT4—底部)。仅当表达用于完全糖链的酶时，可以检测到具有对应于完全糖基化的产物QA-TriR-FRXX或QA-TriR-FRXA(MW＝1526.68)的质量离子(m/z＝1526)的峰，但是在对照中检测不到(顶部)。NB：在该实验中，不包括UDP-芹菜糖/UDP-木糖合酶(QsAXS1)。
图20证实了QsAXS1对于C-28四糖链的高效芹菜糖化的重要性。表达了QA-TriR-FRX生产所必需的酶组(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850+Qs-28-O-FucT+Qs-28-O-RhaT+Qs-28-O-XylT3+QsFucSyn(FucSyn)—顶部)。在不存在(中间)或存在(底部)QsAXS1(AXS)的情况下表达了QA-TriR-FRXA生产所必需的酶组(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850+Qs-28-O-FucT+Qs-28-O-RhaT+Qs-28-O-XylT3+Qs-28-O-ApiT4+QsFucSyn)。显示了QA-TriR-FRXA产物的分子量(MW＝1526.68)的提取离子色谱图(EIC)。在缺少芹菜糖基转移酶Qs-28-O-ApiT的对照植物(顶部)中，不存在QA-TriR-FRXA产物的信号。通过芹菜糖基转移酶Qs-28-O-ApiT的表达(中间)，11.6分钟处的小信号是可见的。在该时间点的质谱分析显示主要离子为1394，对应于如对照中所示的QA-TriR-FRX产物，表明该产物不良转化为QA-TriR-FRXA。最终，QsAXS1酶与QA-TriR-FRXA酶的共表达导致1526离子大幅升高(底部)。因此，这是质谱中11.6min处最大量的产物(NB：由于13C掺入的升高，这主要作为1527处的离子可见)。
图21显示了QsFucSyn和ATCV-1的共表达对QA-TriR-F得率的影响的比较。在本氏烟草(N.benthamiana)中瞬时共表达QA-TriR-F生产所必需的基因组(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850+Qs-28-O-FucT)。另外，进行了绿色荧光蛋白(GFP，阴性对照)、QsFucSyn、ATCV-1或QsFucSyn和ATCV-1两者一起的共表达。在瞬时表达后，通过LC-CAD相对于内标(洋地黄毒苷，1.1μg/mg干叶片)测量了本氏烟草(N.benthamiana)叶提取物中QA-TriR和QA-TriR-F的相对水平。所有样品重复测量三次(n＝3)。误差线表示标准偏差。
图22显示了QsFucSyn-样酶的共表达对QA-TriR-F得率的影响的比较。在本氏烟草(N.benthamiana)中瞬时共表达QA-TriR-F生产所必需的基因组(AstHMGR+QsbAS+QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCslG2+Qs-3-O-GalT+Qs_0283850+Qs-28-O-FucT)。另外，共表达了绿色荧光蛋白(GFP，阴性对照)、QsFucSyn(阳性对照)或者来自皂树(Q.saponaria)(QsFSL-1和QsFSL-2)或肥皂草(Saponaria officinalis)(SoFSL-1)的三种FucSyn-样蛋白中的一种。在瞬时表达后，通过LC-CAD相对于内标(洋地黄毒苷，1.1μg/mg干叶片)测量了本氏烟草(N.benthamiana)叶提取物中QA-TriR-F的相对水平。
图23显示QsFucSyn和同源物(即FucSyn-样蛋白)可能是SDR114C家族成员。在MegaX(Kumar等人,2016)中使用邻接法(Saitou&Nei,1987)实施了系统发育分析。结节标记显示了自举值百分比(5000个重复)。树中所使用的基因的登录号为：胡椒薄荷(M.piperita)薄荷醇脱氢酶(AAQ55960)、胡椒薄荷(M.piperita)新薄荷醇脱氢酶(AAQ55959)、胡椒薄荷(M.piperita)异薄荷二烯酮还原酶(AAQ75422)、辣椒(C.annuum)薄荷酮还原酶(ABU54321)、拟南芥(A.thaliana)CytADR1(NP_001190151)、拟南芥(A.thaliana)CytADR2(NP_179996)、大红罂粟(P.bracteatum)沙罗泰里啶还原酶(A4UHT7)、拟南芥(A.thaliana)羟基类固醇脱氢酶(NP_568742)、拟南芥(A.thaliana)托品酮还原酶-样(NP_196225)、水稻(O.sativa)MAS(XP_015634207)、胡椒薄荷(M.piperita)异薄荷烯醇脱氢酶(AAU20370)、拟南芥(A.thaliana)ADH(NP_566097)、番茄(S.lycopersicum)GAME25(NP_001233856)、黄花毛地黄(D.lanata)3羟基类固醇还原酶(AAW31720)、拟南芥(A.thaliana)松脂醇还原酶1(Q9FVQ6)、罗勒(O.basilicum)丁香酚合酶1(Q15GI4)、紫花苜蓿(M.sativa)异黄酮还原酶(P52575)、玉米(Z.mays)无色花色苷还原酶(ACG33275)、拟南芥(A.thaliana)花青素还原酶(NP_176365)、紫花苜蓿(M.sativa)Vestitone还原酶(Q40316)、罂粟(P.somniferum)那可丁合酶(I3PLR3)、拟南芥(A.thaliana)二氢黄酮醇-4-还原酶(XP_020884177)、蒺藜苜蓿(M.truncatula)6-脱氧查耳酮合酶(XP_003618003)、罂粟(P.somniferum)可待因酮还原酶(Q9SQ70)、拟南芥(A.thaliana)醛酮还原酶(NP_176203)。
图24显示了菠菜Yossoside I途径和通过SpolFSL的加强作用。A)菠菜YossosideI生物合成途径。SOAP6基因催化苜蓿酸3-O-葡萄糖苷酸D-岩藻糖基化以形成Yossoside I。B)菠菜FucSyn-样(SpolFSL)酶与Yossoside I基因组的瞬时表达导致本氏烟草(N.benthamiana)中Yossoside I积累增强。作为LC-MS提取离子色谱图(EIC)显示了m/z823(Yossoside I)和m/z 809(内标洋地黄毒苷)的数据。顶部小图显示了无SOAP6 D-岩藻糖基转移酶的Yossoside基因组(AstHMGR/QsbAS/QsCYP716-C-28/SOAP3/SOAP4/SOAP5)。中间小图显示当包括SOAP6时，Yossoside I(m/z 823，12.3min)的小幅度积累。底部小图显示当包括菠菜FucSyn-样酶SpolFSL时，Yossoside I的加强。C)当在本氏烟草(N.benthamiana)中单独(左图)或者与菠菜SpolFSL(中间)或QsFucSyn酶(右图)一起瞬时表达完整Yossoside I基因组时，Yossoside I含量的定量(基于LC-CAD峰面积)。
图25显示了SpolFSL及其它FucSyn-样蛋白对加强QA-TriR-F含量的影响。A)将用于生产QA-TriR-F的基因组(AstHMGR/QsbAS/QsCYP716-C-28/QsCYP716-C-16α/QsCYP714-C-23/QsCSL2/Qs-3-O-GalT/Qs-3-O-RhaT/Qs-28-O-FucT)在本氏烟草(N.benthamiana)中瞬时表达。另外，共表达来自皂树(Quillaja Saponaria)(FucSyn(QsFucSyn)、FucSyn-样蛋白1(QsFSL-1)和FucSyn-样蛋白2(QsFSL-2))、菠菜(Spinacia oleracea)(SpolFSL)和肥皂草(Saponaria officinalis)(SoFSL)的多种FucSyn蛋白，并且通过LC-CAD测量这些基因对QA-TriR-F含量的影响。B)多种FucSyn-样蛋白之间的成对蛋白序列同一性百分比。
图26显示了皂皮酸3-O-{α-L-吡喃鼠李糖基-(1→3)-[β-D-吡喃半乳糖基-(1→2)]-β-D-吡喃葡糖苷酸}-28-O-[β-D-吡喃岩藻糖基](QA-TriR-F)在MeOH-d4中的1H和13C-NMR光谱数据(600，150MHz)。
图27显示了皂皮酸3-O-{α-L-吡喃鼠李糖基-(1→3)-[β-D-吡喃半乳糖基-(1→2)]-β-D-吡喃葡糖苷酸}-28-O-{[α-L-吡喃鼠李糖基-(1→2)-[β-D-吡喃岩藻糖基]}(QA-TriR-FR)在MeOH-d4中的1H和13C-NMR光谱数据(600，150MHz)。
图28显示了皂皮酸3-O-{α-L-吡喃鼠李糖基-(1→3)-[β-D-吡喃半乳糖基-(1→2)]-β-D-吡喃葡糖苷酸}-28-O-{[β-D-吡喃木糖基-(1→4)-α-L-吡喃鼠李糖基-(1→2)-[β-D-吡喃岩藻糖基]}(QA-TriR-FRX)在MeOH-d4/D2O，10:1中的1H和13C-NMR光谱数据(600，150MHz)。
图29显示了皂皮酸3-O-{α-L-吡喃鼠李糖基-(1→3)-[β-D-吡喃半乳糖基-(1→2)]-β-D-吡喃葡糖苷酸}-28-O-{[β-D-吡喃木糖基-(1→3)-[β-D-吡喃木糖基-(1→4)-α-L-吡喃鼠李糖基-(1→2)-[β-D-吡喃岩藻糖基]}(QA-TriR-FRXX)在MeOH-d4/D2O，10:1中的1H和13C-NMR光谱数据(600，150MHz)。
图30显示了皂皮酸3-O-{α-L-吡喃鼠李糖基-(1→3)-[β-D-吡喃半乳糖基-(1→2)]-β-D-吡喃葡糖苷酸}-28-O-{[β-D-呋喃芹菜糖基-(1→3)-[β-D-吡喃木糖基-(1→4)-α-L-吡喃鼠李糖基-(1→2)-[β-D-吡喃岩藻糖基]}(QA-TriR-FRXA)在MeOH-d4/D2O，10:1中的1H和13C-NMR光谱数据(600，150MHz)。
具体实施方式
本发明的第一方面是制备QA-FRX(X/A)的方法，其中将FRX(X/A)链加入至QA的C-28位，所述方法包括：
(i)(a)将QA与UDP-α-D-岩藻糖和酶Qs-28-O-FucT(SEQ ID NO 2)或者具有至少70％序列同一性的序列的酶合并，和/或
(b)将QA与UDP-4-酮,6-脱氧-D-葡萄糖、酶Qs-28-O-FucT(SEQ ID NO 2)或者具有至少70％序列同一性的序列的酶，和酶QsFucSyn(SEQ ID NO 12)或者具有至少45％序列同一性的序列的酶合并以形成QA-F；然后
(ii)将QA-F与UDP-β-L-鼠李糖和酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有至少70％序列同一性的序列的酶合并以形成QA-FR；
(iii)将QA-FR与UDP-α-D-木糖和酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有至少70％序列同一性的序列的酶合并以形成QA-FRX；和
(iv)将QA-FRX与UDP-α-D-木糖和酶Qs-28-O-XylT4(SEQ ID NO 8)或者具有至少70％序列同一性的序列的酶合并以形成QA-FRXX，和/或将QA-FRX与UDP-α-D-芹菜糖和酶Qs-28-O-ApiT4(SEQ ID NO 10)或者具有至少70％序列同一性的序列的酶合并以形成QA-FRXA。
在本申请中所讨论的序列同一性百分比是通过SEQ ID NO所识别的序列全长间的序列同一性百分比。这可以包括缩短的序列，它具有在缩短的序列长度间所测量的相同序列同一性。不考虑缩短序列的长度，缩短序列可以具有SEQ.ID.NO.的序列同一性百分比的相同同源性。缩短序列可以是全长序列长度的至少一半，优选地全长序列长度的至少四分之三。
在本发明的该方面中，糖供体是UDP-糖。如果糖供体是游离糖，则在本发明的第一方面所述的方法中使用前，将它们转化为UDP-糖。
优选地，在生物系统中实施本发明的第一方面所述的方法。所述生物系统是植物或微生物，将编码一种或多种本发明第一方面所述的酶的核酸引入至该生物系统中。大多数情况下，生物系统不会天然表达任何本发明的第一方面所述的酶，并因此将所述生物系统工程化以表达所有五种酶。如果宿主不天然产生如本发明的第一方面所需要的UDP-糖，则还将所述系统工程化以产生这些糖。优选地，所述生物系统天然产生这些糖，例如，本氏烟草(N.benthamiana)，或者可以工程化以产生这些糖，例如，酵母。
在本氏烟草(N.benthamiana)中，多种UDP-糖(例如，UDP-鼠李糖)天然存在于该植物中。将本发明的第一方面的UGT酶(UDP-依赖性糖基转移酶)工程化以通过植物表达，并且获得生物合成产生QA衍生物的途径。UDP-糖可以存在，但不是大量存在，因此限制了所产生的产物的量。例如，UDP-α-D-芹菜糖和UDP-α-D-岩藻糖不能大量存在于本氏烟草(N.benthamiana)中。解决该问题并提高这些糖的水平的一种方法是还将宿主植物工程化以产生更多的糖和/或通过将宿主植物工程化以表达一种或多种加强酶。UDP-α-D-芹菜糖的加强酶可以是QsAXS1(SEQ ID No.14)。UDP-α-D-岩藻糖的加强酶可以是QsFucSyn(SEQID No.12)、ATCV-1(SEQ.ID No 40)或QsFucSyn-样酶，如QsFSL-1(SEQ ID No.48)、QsFSL-2(SEQ ID No 50)、SoFSL-1(SEQ ID No 52)或SpolFSL(SEQ ID NO 54)，如以下所讨论的。如果UDP-α-D-岩藻糖不大量存在，则解决该问题的另一种方法是将QA与UDP-4-酮,6-脱氧-D-葡萄糖、Qs-28-O-FucT(SEQ ID NO 2)或者具有至少70％序列同一性的序列的酶，以及QsFucSyn(SEQ ID NO 12)或者具有至少45％序列同一性的序列的酶合并以形成QA-F。
如图1所述，通过向QA主链连续添加形成C-28四糖链的糖单元来形成QA-Tri(X/R)-FRX(X/A)或QA-FRX(X/A)。通过以β-键将D-岩藻糖连接至包含QA的分子以形成包含QA-F的分子来起始QA核心的C-28位处的直链四糖。该步骤之后是以α-键将L-鼠李糖连接至包含QA-F的分子，以产生包含QA-FR的分子。然后，以β-键将D-木糖连接至包含QA-FR的分子以产生包含QA-FRX的分子。最终，以β-键将D-木糖连接至包含QA-FRX的分子以产生包含QA-FRXX的分子，并且以β-键将D-芹菜糖连接至包含QA-FRX的分子以产生包含QA-FRXA的分子。
在以下描述中，对于当通过以β-键将D-岩藻糖连接至包含QA的分子以形成包含QA-F的分子来起始包含QA核心的分子的C-28位处的直链四糖时的情况，描述了本发明所述的方法。
优选地实施所述方法，从而可以分离出包含QA-FRX(X/R)的分子或将其进一步衍生化以化学合成下游产物，如QS-21。
在本发明的该方面中，QA衍生物是QA-FRXX(或QA-Tri(X/R)-FRXX)或QA-FRXA(或QA-Tri(X/R)-FRXA)或者包含QA-FRXX和QA-FRXA(或QA-Tri(X/R)-FRXX和QA-Tri(X/R)-FRXA)的混合物。当QA衍生物是包含QA-FRXX和QA-FRXA(或者QA-Tri(X/R)-FRXX和QA-Tri(X/R)-FRXA)的混合物时，QA-FRXX与QA-FRXA(或者QA-Tri(X/R)-FRXX与QA-Tri(X/R)-FRXA)之比可以改变。混合物内QA-FRXX与QA-FRXA(或者QA-Tri(X/R)-FRXX与QA-Tri(X/R)-FRXA)之比的百分比可以改变。适合地，所述混合物包含10％至90％的QA-FRXX(或QA-Tri(X/R)-FRXX)，如10％、20％、30％、40％、50％、60％、70％、80％或90％，和90％至10％的QA-FRXA(或QA-Tri(X/R)-FRXA)，如90％、80％、70％、60％、50％、40％、30％、20％或10％。优选地，所述混合物包含60％的QA-FRXX(或QA-Tri(X/R)-FRXX)和40％的QA-FRXA(或QA-Tri(X/R)-FRXA)，或者各50％。
在QA-TriR或QA-TriX中，连接至C-3位的糖是β-D-葡糖醛酸(GlcpA)，如图3所示。GlcpA残基可以具有两个与之连接的糖。连接至GlcpA残基的一个糖是D-吡喃半乳糖(Galp)。可以以β-1,2-键连接D-吡喃半乳糖。连接至GlcpA残基的一个糖可以是D-吡喃木糖(Xylp)或者L-吡喃鼠李糖(Rhap)。可以分别以β-1,3-键或者α-1,3-键连接D-吡喃木糖或者L-吡喃鼠李糖。
本发明的第一方面所述的方法的第一步是以β-键将D-岩藻糖连接至包含QA的分子，所述分子可以是QA-TriR和/或QA-TriX。通过酶Qs-28-O-FucT(SEQ ID NO 2)或者通过具有与Qs-28-O-FucT具有至少70％序列同一性的序列的酶实施该步骤。该酶能够将D-岩藻糖以β-键转移至包含QA的分子的C-28位。例如，可以通过在本氏烟草(N.benthamiana)中瞬时表达来确定酶的功能，如材料和方法以及实施例2中所述。简要地，编码要测试的酶的基因与产生如QA-TriX的分子所需的基因(参见PCT/EP2020/067866，作为WO 2020/260475公开)(如AstHMGR(SEQ ID No 15)、QsbAS(SEQ ID NO 17)、QsCYP716-C-28(SEQ ID NO 19)、QsCYP716-C-16α(SEQ ID NO 21)、QsCYP714-C-23(SEQ ID NO 23)、CslG2(SEQ ID NO 27)、Qs-3-O-GalT(SEQ ID NO 29)、Qs_0283870(SEQ ID NO 37))或者QA-TriR(参见PCT/EP2020/067866)4(如AstHMGR(SEQ ID No 15)、QsbAS(SEQ ID NO 17)、QsCYP716-C-28(SEQID NO 19)、QsCYP716-C-16α(SEQ ID NO 21)、QsCYP714-C-23(SEQ ID NO 23)、CslG2(SEQID NO 27)、Qs-3-O-GalT(SEQ ID NO 29)、Qs_0283850(SEQ ID NO 35))一起共表达应导致产生岩藻糖基化产物，分别为QA-TriX-F(单同位素质量＝1102.52，[M-H]-＝1101)或者QA-TriR-F(单同位素质量＝1116.54，[M-H]-＝1115)。可以通过如材料和方法中所述的大规模浸润、产物纯化和通过NMR的结构确认来确认产物的身份，作为另外一种选择，可以通过如材料和方法中所述的LC-MS，以及通过QA-TriX-F或QA-TriR-F的标准品所获得的峰的保留时间和质量的比较，或者通过与通过产生QA-TriX或者QA-TriR所需的上述基因与岩藻糖基转移酶Qs-28-O-FucT的基因(SEQ ID NO 1)的共表达所获得的产物的比较，来确认产物的身份。
酶Qs-28-O-FucT的序列的序列同一性百分比可以改变。所述序列同一性可以是与SEQ ID NO 2至少70％、75％、80％、85％、90％或95％的同一性。因此，在一些实施方式中，在本发明所述的方法中所使用的酶Qs-28-O-FucT与SEQ ID NO 2具有至少70％、75％、80％、85％、90％或95％的序列同一性，适合地至少90％，更适合地至少95％的序列同一性。
本发明的第一方面所述的方法的替代性的第一步是将UDP-4-酮,6-脱氧-D-葡萄糖连接至包含QA的分子，所述分子可以是QA-TriR和/或QA-TriX，然后在C-4位实施酮还原。通过酶Qs-28-O-FucT(SEQ ID NO 2)或者通过具有与Qs-28-O-FucT具有至少70％序列同一性的序列的酶，和酶QsFucSyn(SEQ ID NO 12)或者具有与QsFucSyn具有至少45％序列同一性的序列的酶实施该步骤。在本发明的第二方面更详细地讨论该步骤。
本发明的第一方面所述的方法的第二步是将α-L-鼠李糖连接至β-D-岩藻糖残基。通过酶Qs-28-O-RhaT(SEQ ID NO 4)或者通过具有与Qs-28-O-RhaT具有至少70％序列同一性的序列的酶实施该步骤。所述酶能够将L-鼠李糖转移至D-岩藻糖残基。例如，可以通过在本氏烟草(N.benthamiana)中瞬时表达来确定酶的功能，如材料和方法以及实施例3中所述。简要地，编码要测试的酶的基因与产生如QA-TriX-F的分子所需的基因(如AstHMGR(SEQID No 15)、QsbAS(SEQ ID NO 17)、QsCYP716-C-28(SEQ ID NO 19)、QsCYP716-C-16α(SEQID NO 21)、QsCYP714-C-23(SEQ ID NO 23)、CslG2(SEQ ID NO 27)、Qs-3-O-GalT(SEQ IDNO 29)、Qs_0283870(SEQ ID NO 37)、Qs-28-O-FucT(SEQ ID NO 1))或者QA-TriR-F(如AstHMGR(SEQ ID No 15)、QsbAS(SEQ ID NO 17)、QsCYP716-C-28(SEQ ID NO 19)、QsCYP716-C-16α(SEQ ID NO 21)、QsCYP714-C-23(SEQ ID NO 23)、CslG2(SEQ ID NO 27)、Qs-3-O-GalT(SEQ ID NO 29)、Qs_0283850(SEQ ID NO 35)、Qs-28-O-FucT(SEQ ID NO 1))一起共表达应该导致产生鼠李糖基化产物，分别为QA-TriX-FR(单同位素质量＝1248.58，[M-H]-＝1247)或者QA-TriR-FR(单同位素质量＝1262.59，[M-H]-＝1261)。可以通过如材料和方法中所述的大规模浸润、产物纯化和通过NMR的结构确认来确认产物的身份，作为另外一种选择，可以通过如材料和方法中所述的LC-MS，以及通过QA-TriX-FR或QA-TriR-FR的标准品所获得的峰的保留时间和质量的比较，或者通过与通过产生QA-TriX-F或者QA-TriR-F所需的上述基因与鼠李糖基转移酶Qs-28-O-RhaT的基因(SEQ ID NO 3)的共表达所获得的产物的比较，来确认产物的身份。
酶Qs-28-O-RhaT的序列的序列同一性百分比可以改变。所述序列同一性可以是与SEQ ID NO 4至少70％、75％、80％、85％、90％或95％的同一性。因此，在一些实施方式中，在本发明所述的方法中所使用的酶Qs-28-O-RhaT与SEQ ID NO 4具有至少70％、75％、80％、85％、90％或95％的序列同一性，适合地至少90％，更适合地至少95％的序列同一性。
本发明的第一方面所述的方法的第三步是将β-D-木糖连接至α-L-鼠李糖残基。通过酶Qs-28-O-XylT3(SEQ ID NO 6)或者通过具有与Qs-28-O-XylT3具有至少70％序列同一性的序列的酶实施该步骤。所述酶能够转移D-木糖。例如，可以通过在本氏烟草(N.benthamiana)中瞬时表达来确定酶的功能，如材料和方法以及实施例4中所述。简要地，编码要测试的酶的基因与产生如QA-TriX-FR的分子所需的基因(如AstHMGR(SEQ ID No15)、QsbAS(SEQ ID NO 17)、QsCYP716-C-28(SEQ ID NO 19)、QsCYP716-C-16α(SEQ ID NO21)、QsCYP714-C-23(SEQ ID NO 23)、CslG2(SEQ ID NO 27)、Qs-3-O-GalT(SEQ ID NO29)、Qs_0283870(SEQ ID NO 37)、Qs-28-O-FucT(SEQ ID NO 1)、Qs-28-O-RhaT(SEQ ID NO3))或者QA-TriR-FR(如AstHMGR(SEQ ID No 15)、QsbAS(SEQ ID NO 17)、QsCYP716-C-28(SEQ ID NO 19)、QsCYP716-C-16α(SEQ ID NO 21)、QsCYP714-C-23(SEQ ID NO 23)、CslG2(SEQ ID NO 27)、Qs-3-O-GalT(SEQ ID NO 29)、Qs_0283850(SEQ ID NO 35)、Qs-28-O-FucT(SEQ ID NO 1)、Qs-28-O-RhaT(SEQ ID NO 3))一起共表达应该导致产生木糖基化产物，分别为QA-TriX-FRX(单同位素质量＝1380.62，[M-H]-＝1379)或者QA-TriR-FRX(单同位素质量＝1394.64，[M-H]-＝1393)。可以通过如材料和方法中所述的大规模浸润、产物纯化和通过NMR的结构确认来确认产物的身份，作为另外一种选择，可以通过如材料和方法中所述的LC-MS，以及通过与QA-TriX-FRX或QA-TriR-FRX的标准品所获得的峰的保留时间和质量的比较，或者通过与通过产生QA-TriX-FR或者QA-TriR-FR所需的上述基因与木糖基转移酶Qs-28-O-XylT3的基因(SEQ ID NO 5)的共表达所获得的产物的比较，来确认产物的身份。
酶Qs-28-O-XylT3的序列的序列同一性百分比可以改变。所述序列同一性可以是与SEQ ID NO 6至少70％、75％、80％、85％、90％或95％的同一性。因此，在一些实施方式中，在本发明所述的方法中所使用的酶Qs-28-O-XylT3与SEQ ID NO 6具有至少70％、75％、80％、85％、90％或95％的序列同一性，适合地至少90％，更适合地至少95％的序列同一性。
本发明的第一方面所述的方法的第四步是将β-D-木糖连接至β-D-木糖残基。通过酶Qs-28-O-XylT4(SEQ ID NO 8)或者通过具有与Qs-28-O-XylT4具有至少70％序列同一性的序列的酶实施该步骤。所述酶能够转移D-木糖。例如，可以通过在本氏烟草(N.benthamiana)中瞬时表达来确定酶的功能，如材料和方法以及实施例5中所述。简要地，编码要测试的酶的基因与产生如QA-TriX-FRX的分子所需的基因(如AstHMGR(SEQ ID No15)、QsbAS(SEQ ID NO 17)、QsCYP716-C-28(SEQ ID NO 19)、QsCYP716-C-16α(SEQ ID NO21)、QsCYP714-C-23(SEQ ID NO 23)、CslG2(SEQ ID NO 27)、Qs-3-O-GalT(SEQ ID NO29)、Qs_0283870(SEQ ID NO 37)、Qs-28-O-FucT(SEQ ID NO 1)、Qs-28-O-RhaT(SEQ ID NO3)、Qs-28-O-XylT3(SEQ ID NO 5))或者QA-TriR-FRX(如AstHMGR(SEQ ID No 15)、QsbAS(SEQ ID NO 17)、QsCYP716-C-28(SEQ ID NO 19)、QsCYP716-C-16α(SEQ ID NO 21)、QsCYP714-C-23(SEQ ID NO 23)、CslG2(SEQ ID NO 27)、Qs-3-O-GalT(SEQ ID NO 29)、Qs_0283850(SEQ ID NO 35)、Qs-28-O-FucT(SEQ ID NO 1)、Qs-28-O-RhaT(SEQ ID NO 3)、Qs-28-O-XylT3(SEQ ID NO 5))一起共表达应该导致产生木糖基化产物，分别为QA-TriX-FRXX(单同位素质量＝1512.66，[M-H]-＝1511)或者QA-TriR-FRXX(单同位素质量＝1526.68，[M-H]-＝1525)。可以通过如材料和方法中所述的大规模浸润、产物纯化和通过NMR的结构确认来确认产物的身份，作为另外一种选择，可以通过如材料和方法中所述的LC-MS，以及与QA-TriX-FRXX或QA-TriR-FRXX的标准品所获得的峰的保留时间和质量的比较，或者通过与通过产生QA-TriX-FRX或者QA-TriR-FRX所需的上述基因与木糖基转移酶Qs-28-O-XylT4的基因(SEQ ID NO 7)的共表达所获得的产物的比较，来确认产物的身份。
酶Qs-28-O-XylT4的序列的序列同一性百分比可以改变。所述序列同一性可以是与SEQ ID NO 8至少70％、75％、80％、85％、90％或95％的同一性。因此，在一些实施方式中，在本发明所述的方法中所使用的酶Qs-28-O-XylT4与SEQ ID NO 8具有至少70％、75％、80％、85％、90％或95％的序列同一性，适合地至少90％，更适合地至少95％的序列同一性。
本发明的第一方面所述的方法的替代性第四步是将β-D-芹菜糖连接至β-D-木糖残基。通过酶Qs-28-O-ApiT4(SEQ ID NO 10)或者通过具有与Qs-28-O-ApiT4具有至少70％序列同一性的序列的酶实施该步骤。所述酶优选地能够转移D-芹菜糖。例如，可以通过在本氏烟草(N.benthamiana)中瞬时表达来确定酶的功能，如材料和方法以及实施例5中所述。简要地，编码要测试的酶的基因与编码QsAXS1的基因(SEQ ID NO 13)以及产生如QA-TriX-FRX的分子所需的基因(如AstHMGR(SEQ ID No 15)、QsbAS(SEQ ID NO 17)、QsCYP716-C-28(SEQ ID NO 19)、QsCYP716-C-16α(SEQ ID NO 21)、QsCYP714-C-23(SEQ ID NO 23)、CslG2(SEQ ID NO 27)、Qs-3-O-GalT(SEQ ID NO 29)、Qs_0283870(SEQ ID NO 37)、Qs-28-O-FucT(SEQ ID NO 1)、Qs-28-O-RhaT(SEQ ID NO 3)、Qs-28-O-XylT3(SEQ ID NO 5))或者QA-TriR-FRX(如AstHMGR(SEQ ID No 15)、QsbAS(SEQ ID NO 17)、QsCYP716-C-28(SEQ IDNO 19)、QsCYP716-C-16α(SEQ ID NO 21)、QsCYP714-C-23(SEQ ID NO 23)、CslG2(SEQ IDNO 27)、Qs-3-O-GalT(SEQ ID NO 29)、Qs_0283850(SEQ ID NO 35)、Qs-28-O-FucT(SEQ IDNO 1)、Qs-28-O-RhaT(SEQ ID NO 3)、Qs-28-O-XylT3(SEQ ID NO 5))一起共表达应该导致产生芹菜糖基化产物，分别为QA-TriX-FRXA(单同位素质量＝1512.66，[M-H]-＝1511)或者QA-TriR-FRXA(单同位素质量＝1526.68，[M-H]-＝1525)。可以通过如材料和方法中所述的大规模浸润、产物纯化和通过NMR的结构确认来确认产物的身份，作为另外一种选择，可以通过如材料和方法中所述的LC-MS，以及与QA-TriX-FRXA或QA-TriR-FRXA的标准品所获得的峰的保留时间和质量的比较，或者通过与通过产生QA-TriX-FRX或者QA-TriR-FRX所需的上述基因与QsAXS1的基因(SEQ ID NO 13)和芹菜糖基转移酶Qs-28-O-ApiT4的基因(SEQID NO 9)的共表达所获得的产物的比较，来确认产物的身份。
酶Qs-28-O-ApiT4的序列的序列同一性百分比可以改变。所述序列同一性可以是与SEQ ID NO 10至少70％、75％、80％、85％、90％或95％的同一性。因此，在一些实施方式中，在本发明所述的方法中所使用的酶Qs-28-O-ApiT4与SEQ ID NO 10具有至少70％、75％、80％、85％、90％或95％的序列同一性，适合地至少90％，更适合地至少95％的序列同一性。
所述序列与Qs-28-O-FucT、Qs-28-O-RhaT、Qs-28-O-XylT3、Qs-28-O-ApiT4和Qs-28-O-ApiT4的序列同一性百分比均可以是相同或不同的。
可以体外实施本发明的第一方面所述的方法。在本发明的意义上，“体外”表示用本发明的适当酶酶促处理适当的QA衍生物。可以生物合成产生或化学合成QA衍生物。酶可以经化学合成或者从它们的天然环境中纯化出来。确定酶促处理的最优条件(例如，持续时间、温度、缓冲液等)是在技术人员的范围内。可以(例如)通过经由如材料和方法中所述的NMR阐明其结构来确认QA衍生物的身份。在一个实施方式中，本发明的第一方面所述的制备QA-FRX(X/A)的体外方法包括在存在UDP-α-D-岩藻糖、UDP-β-L-鼠李糖、UDP-α-D-木糖和UDP-α-D-芹菜糖的情况下，用包含Qs-28-O-FucT(SEQ ID NO 2)、Qs-28-O-RhaT(SEQ ID NO4)、Qs-28-O-XylT3(SEQ ID NO 6)、Qs-28-O-XylT4(SEQ ID NO 8)和Qs-28-O-ApiT4(SEQID NO 10)的酶的混合物酶促处理包含QA的分子(例如，QA或者QA-Tri(X/R))。
优选地，在生物系统中实施本发明的第一方面所述的方法。将编码上述酶中的一种或多种的核酸引入生物系统中并在生物系统中表达。
所述生物系统可以是植物或微生物。当生物系统是植物时，所述植物可以是行栽作物，例如，向日葵、马铃薯、油菜、干豆、豌豆、亚麻、红花、荞麦、棉、玉米、大豆和甜菜。所述植物还可以是玉米、小麦、油菜和水稻。优选地，所述植物可以是本氏烟草(Nicotianabenthamiana)。
在本发明的某些方面，所述生物系统不是皂树(Quillaja Saponaria)。
当所述生物系统是微生物时，所述微生物可以是细菌或酵母。
酵母(酿酒酵母(Saccharomyces cerevisiae))是用于生产高价值小分子，包括萜烯的异源宿主。像植物一样，酵母内源产生三萜前体2,3-氧化鲨烯，并因此是用于工业规模生产三萜的有前景的宿主。它也是在内质网膜功能性表达植物CYP的非常有效的宿主。通过内源酵母酶对三萜骨架进行最小程度的修饰，从而促进产物纯化。酵母可以是生产含有多种糖苷缀合物的三萜的生产宿主，该糖苷缀合物包含为直链和支链结构的多种类型的糖。酵母中的糖基化反应受内源糖供体的有限模板的限制。然而，通过表达来自高等植物的基因，酵母的核苷酸糖代谢可以扩大到UDP-葡萄糖和UDP-半乳糖以外，以包括UDP-鼠李糖、UDP-葡糖醛酸、UDP-木糖、UDP-阿拉伯糖等。
本发明的第一方面所述的方法包括通过经由载体将包含QA-FRXX/A的分子的生物合成所需的核酸引入到宿主细胞，来用核酸转化宿主。可以在载体和宿主细胞基因组之间发生重组以将核酸引入宿主细胞基因组。
在一个实施方式中，提供了制备QA-Mono-FRX(X/A)、QA-Di-FRX(X/A)和/或QA-Tri(X/R)-FRX(X/A)的方法，其中在C-3位添加Mono、Di或Tri(X/R)链并且在QA的C-28位添加FRX(X/A)链，所述方法包括：
(i)将QA与UDP-α-D-吡喃葡糖醛酸和酶QsCSL1(SEQ ID NO 26)或QsCslG2(SEQ IDNO 28)或者具有至少70％序列同一性的序列的酶合并以形成QA-Mono；任选地
(ii)将QA-Mono与UDP-α-D-吡喃半乳糖和酶Qs-3-O-GalT(SEQ ID NO 30)或者具有至少70％序列同一性的序列的酶合并以形成QA-Di；任选地
(iii)将QA-Di与UDP-β-L-吡喃鼠李糖和酶DN20529_c0_g2_i8(SEQ ID NO 36)或Qs_0283850(SEQ ID NO 34)，或者Qs-3-O-RhaT/XylT(SEQ ID NO 32)或具有至少70％序列同一性的序列的酶合并以形成QA-TriR，和/或将QA-Di与UDP-α-D-吡喃木糖和酶Qs_0283870(SEQ ID NO 38)或Qs-3-O-RhaT/XylT(SEQ ID NO 32)或具有至少70％序列同一性的序列的酶合并以形成QA-TriX；
(iv)(a)将QA-Mono、QA-Di和/或QA-Tri(R/X)与UDP-α-D-岩藻糖和酶Qs-28-O-FucT(SEQ ID NO 2)或具有至少70％序列同一性的序列的酶合并以形成QA-Mono-F、QA-Di-F和/或QA-Tri(R/X)-F，和/或
(b)将QA-Mono、QA-Di和/或QA-Tri(R/X)与UDP-4-酮,6-脱氧-D-葡萄糖、酶Qs-28-O-FucT(SEQ ID NO 2)或具有至少70％序列同一性的序列的酶，和酶QsFucSyn(SEQ ID NO12)或具有至少45％序列同一性的序列的酶合并以形成QA-Mono-F、QA-Di-F和/或QA-Tri(R/X)-F；
(v)将QA-Mono-F、QA-Di-F和/或QA-Tri(R/X)-F与UDP-β-L-鼠李糖和酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有至少70％序列同一性的序列的酶合并以形成QA-Mono-FR、QA-Di-FR和/或QA-Tri(R/X)-FR；
(vi)将QA-Mono-FR、QA-Di-FR和/或QA-Tri(R/X)-FR与UDP-α-D-木糖和酶Qs-28-O-XylT3(SEQ ID NO 6)或具有至少70％序列同一性的序列的酶合并以形成QA-Mono-FRX、QA-Di-FRX和/或QA-Tri(R/X)-FRX；和
(vii)将QA-Mono-FRX、QA-Di-FRX和/或QA-Tri(R/X)-FRX与UDP-α-D-木糖和酶Qs-28-O-XylT4(SEQ ID NO 8)或具有至少70％序列同一性的序列的酶合并以形成QA-Mono-FRXX、QA-Di-FRXX和/或QA-Tri(R/X)-FRXX，和/或将QA-Mono-FRX、QA-Di-FRX和/或QA-Tri(R/X)-FRX与UDP-α-D-芹菜糖和酶Qs-28-O-ApiT4(SEQ ID NO 10)或具有至少70％序列同一性的序列的酶合并以形成QA-Mono-FRXA、QA-Di-FRXA和/或QA-Tri(R/X)-FRXA。
在其它实施方式中，提供了在宿主中制备生物合成的3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-呋喃芹菜糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸(QA-TriR-FRXA)的方法，所述方法包括以下步骤：a)表达QA-TriR生物合成所需的基因，和b)将编码酶Qs-28-O-FucT(SEQ ID NO 2)或具有与SEQ ID NO 2具有至少70％序列同一性的序列的酶；酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有与SEQ ID NO 4具有至少70％序列同一性的序列的酶；酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有与SEQ ID NO 6具有至少70％序列同一性的序列的酶；和酶Qs-28-O-ApiT4(SEQ ID NO 10)或者具有与SEQ ID NO 10具有至少70％序列同一性的序列的酶的核酸分子引入宿主。
在其它实施方式中，提供了在宿主中制备生物合成的3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸(QA-TriR-FRXX)的方法，所述方法包括以下步骤：a)表达QA-TriR生物合成所需的基因，和b)将编码酶Qs-28-O-FucT(SEQ ID NO 2)或具有与SEQ ID NO 2具有至少70％序列同一性的序列的酶；酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有与SEQ ID NO 4具有至少70％序列同一性的序列的酶；酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有与SEQ ID NO 6具有至少70％序列同一性的序列的酶；和酶Qs-28-O-XylT4(SEQ ID NO 8)或者具有与SEQ ID NO 8具有至少70％序列同一性的序列的酶的核酸分子引入宿主。
在其它实施方式中，提供了在宿主中制备生物合成的3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-呋喃芹菜糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸(QA-TriX-FRXA)的方法，所述方法包括以下步骤：a)表达QA-TriX生物合成所需的基因，和b)将编码酶Qs-28-O-FucT(SEQ ID NO 2)或具有与SEQ ID NO 2具有至少70％序列同一性的序列的酶；酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有与SEQ ID NO 4具有至少70％序列同一性的序列的酶；酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有与SEQ ID NO 6具有至少70％序列同一性的序列的酶；和酶Qs-28-O-ApiT4(SEQ ID NO 10)或者具有与SEQ ID NO 10具有至少70％序列同一性的序列的酶的核酸分子引入宿主。
在其它实施方式中，提供了在宿主中制备生物合成的3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸(QA-TriX-FRXX)的方法，所述方法包括以下步骤：a)表达QA-TriX生物合成所需的基因，和b)将编码酶Qs-28-O-FucT(SEQ ID NO 2)或具有与SEQ ID NO 2具有至少70％序列同一性的序列的酶；酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有与SEQ ID NO 4具有至少70％序列同一性的序列的酶；酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有与SEQ ID NO 6具有至少70％序列同一性的序列的酶；和酶Qs-28-O-XylT4(SEQ ID NO 8)或者具有与SEQ ID NO 8具有至少70％序列同一性的序列的酶的核酸分子引入宿主。
在其它实施方式中，提供了在宿主中制备生物合成的QA-Tri(X/R)-FRX(X/A)的方法，所述方法包括以下步骤：a)表达QA-TriX或QA-TriR生物合成所需的基因，和b)将编码酶Qs-28-O-FucT(SEQ ID NO 2)或具有与SEQ ID NO 2具有至少70％序列同一性的序列的酶；酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有与SEQ ID NO 4具有至少70％序列同一性的序列的酶；酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有与SEQ ID NO 6具有至少70％序列同一性的序列的酶；和酶Qs-28-O-XylT4(SEQ ID NO 8)或具有与SEQ ID NO 8具有至少70％序列同一性的序列的酶和/或酶Qs-28-O-ApiT4(SEQ ID NO 10)或具有与SEQ ID NO 10具有至少70％序列同一性的序列的酶的核酸分子引入宿主。
可以通过以下步骤获得QA-TriR的生物合成：引入编码下列的核酸分子：(i)(a)酶QsCSL1(SEQ ID NO 26)或具有与SEQ ID NO 26具有至少70％序列同一性的序列的酶，或(b)酶QsCslG2(SEQ ID NO 28)或具有与SEQ ID NO 28具有至少70％序列同一性的序列的酶；(ii)酶Qs-3-O-GalT(SEQ ID NO 30)或具有与SEQ ID NO 30具有至少70％序列同一性的序列的酶；和(iii)(a)酶DN20529_c0_g2_i8(SEQ ID NO 36)或具有与SEQ ID NO 36具有至少70％序列同一性的序列的酶，或者(b)酶Qs_0283850(SEQ ID NO 34)或具有与SEQ IDNO 34具有至少70％序列同一性的序列的酶，或者(c)酶Qs-3-O-RhaT/XylT(SEQ ID NO 32)或具有与SEQ ID NO 32具有至少70％序列同一性的序列的酶。
可以通过以下步骤获得QA-TriX的生物合成：引入编码下列的核酸分子：(i)(a)酶QsCSL1(SEQ ID NO 26)或具有与SEQ ID NO 26具有至少70％序列同一性的序列的酶，或(b)酶QsCslG2(SEQ ID NO 28)或具有与SEQ ID NO 28具有至少70％序列同一性的序列的酶；(ii)酶Qs-3-O-GalT(SEQ ID NO 30)或具有与SEQ ID NO 30具有至少70％序列同一性的序列的酶；和(iii)(a)酶Qs_0283870(SEQ ID NO 38)或具有与SEQ ID NO 38具有至少70％序列同一性的序列的酶，或者(b)酶Qs-3-O-RhaT/XylT(SEQ ID NO 32)或具有与SEQID NO 32具有至少70％序列同一性的序列的酶。
本发明的第二方面是根据SEQ ID NO 12的氧化还原酶(QsFucSyn)或者能够提高UDP-α-D-岩藻糖水平的具有至少45％序列同一性的序列的酶。具有与SEQ ID NO 12具有至少45％序列同一性的序列的酶不是SEQ ID NO 54。
酶QsFucSyn的序列的序列同一性百分比可以改变。所述序列同一性可以是与SEQID NO 12至少45％、50％、55％、60％、65％、70％、75％、80％、85％、90％或95％的同一性。
作为另外一种选择，本发明的第二方面的与SEQ ID NO 12(QsFucSyn)具有至少45％序列同一性的氧化还原酶可以是QsFSL-1(SEQ ID No.48)、QsFSL-2(SEQ ID NO 50)或SoFSL-1(SEQ ID NO 52)。
在一些宿主中，UDP-糖可以存在，但不以足够大的量存在，因此限制了所产生的产物的量。在本氏烟草(N.benthamiana)中，UDP-α-D-芹菜糖和UDP-α-D-岩藻糖不是大量存在。解决该问题和提高糖基化产物(例如，芹菜糖基化产物或岩藻糖基化产物)的量的一种方式是提高UDP-糖的水平和/或使用一种或多种糖核苷酸生物合成酶。为了提高芹菜糖基化产物的量，糖核苷酸生物合成酶可以是QsAXS1(SEQ ID No14)。为了提高岩藻糖基化产物的量，糖核苷酸生物合成酶可以是QsFucSyn(SEQ ID NO 12)或者具有UDP-4-酮-6-脱氧-D-葡萄糖4-酮还原酶活性的另一个酶，如QsFSL-1(SEQ ID No.48)、QsFSL-2(SEQ ID No 50)、SoFSL-1(SEQ ID No 52)或SpolFSL(SEQ ID No 54)；或者ATCV-1(SEQ.ID No 40)。
在进行本发明期间，已鉴定D-岩藻糖共浸润或QsFucSyn共表达两者导致岩藻糖基化产物生产的改善。已发现酶的存在提高了岩藻糖基化产物的生产。
QsFucSyn酶是来自皂树(Q.saponaria)的酶。QsFucSyn酶可以参与UDP-D-岩藻糖的生物合成。所提议的从UDP-D-葡萄糖生物合成UDP-D-岩藻糖的第二步包括在C-4位的酮还原。预期QsFucSyn酶实施该第二步，其催化UDP-4-酮-6-脱氧-D-葡萄糖在C-4处的立体选择性还原。作为另外一种选择，所提议的途径包括将UDP-α-D-葡萄糖转化为UDP-4-酮-6-脱氧-葡萄糖中间体。将该中间体添加至QA主链，然后在C-4位发生酮还原以形成岩藻糖基化产物。QsFucSyn酶可以在其添加至QA主链后，将4-酮-6-脱氧-葡萄糖的4-酮基团还原。
在生物系统中，将羧酸(例如QA)与UDP-α-D-岩藻糖和岩藻糖基转移酶合并以形成岩藻糖基化产物将可以是足够的。然而，QsFucSyn酶可以提高UDP-α-D-岩藻糖的生产，其可以导致更高得率的岩藻糖基化产物。的确，更高丰度的UDP-α-D-岩藻糖允许岩藻糖基转移酶更有效地起作用并且有助于β-D-岩藻糖向羧酸更高效的添加。作为另外一种选择，UDP-α-D-葡萄糖可以被转化为UDP-4-酮-6-脱氧-葡萄糖。然后，可以通过将羧酸(例如QA)与UDP-4-酮-6-脱氧-葡萄糖、岩藻糖基转移酶和QsFucSyn酶合并来形成岩藻糖基化产物。据认为第一步包括将(来自UDP-4-酮-6-脱氧-葡萄糖的)4-酮-6-脱氧-葡萄糖添加至QA主链，然后将4-酮基团还原以形成岩藻糖基化产物。QsFucSyn酶可以在其添加至QA主链后，将4-酮-6-脱氧-葡萄糖的4-酮基团还原。在某些方面，QsFucSyn酶还可以帮助将β-D-岩藻糖高效添加至在包含QA的分子(例如QA-Tri(X/R))C-28位处羧酸。在某些方面，一旦将β-D-岩藻糖添加至包含QA的分子(例如QA-Tri(X/R))的C-28位处羧酸，则QsFucSyn酶还可以帮助高效还原UDP-4-酮-6-脱氧-葡萄糖。优选地，当羧酸(如QA或QA-Tri(X/R))与UDP-α-D-葡萄糖合并时，则将岩藻糖基转移酶、QsFucSyn和ATCV-1合并以形成岩藻糖基化产物。
作为另外一种选择，当体外进行反应时，可以在存在UDP-α-D-岩藻糖的情况下，用岩藻糖基转移酶处理羧酸(如QA或QA-Tri(X/R))以形成岩藻糖基化产物，而无需QsFucSyn。作为另外一种选择，当体外进行反应时，可以在存在UDP-α-D-葡萄糖的情况下，用岩藻糖基转移酶、ATCV-1和QsFucSyn处理羧酸，以形成岩藻糖基化产物。
本发明的第三方面包括编码根据本发明的第二方面的酶的核酸分子。
QsFucSyn酶可以(例如)通过根据SEQ ID NO 11的核苷酸序列或者通过借助于简并编码也编码根据本发明的第二方面的酶的序列所编码。
本发明的每种方法可以包括与如根据本发明的第二方面所述的酶合并。
本发明的每种方法可以包括与如根据本发明的第二方面所述的酶和酶ATCV-1合并。
ATCV-1酶是UDP-D-葡萄糖4,6-脱水酶(UGD)并且从UDP-D-葡萄糖产生UDP-4-酮-6-脱氧-D-葡萄糖。这表示UDP-D-岩藻糖生物合成中的第一步(并且也是UDP-L-鼠李糖合成中的第一步)。如以上所讨论的，QsFucSyn酶可以实施所提议的从UDP-D-葡萄糖生物合成UDP-D-岩藻糖中的第二步，从而催化UDP-4-酮-6-脱氧-D-葡萄糖的C-4处的立体选择性还原。作为另外一种选择，将UDP-4-酮-6-脱氧-葡萄糖添加至QA主链，然后将4-酮基团还原以形成岩藻糖基化产物。QsFucSyn酶可以实施4-酮还原。提高UDP-4-酮-6-脱氧-D-葡萄糖在本氏烟草(N.benthamiana)中的可用性可以进一步增强QsFucSyn酶的活性。
本发明的每种方法可以包括与如根据本发明的第二方面所述的酶合并，和与具有UDP-D-葡萄糖4,6-脱水酶活性的一种或多种酶合并。这种酶可以取自UDP-L-鼠李糖生物合成途径。具有UDP-D-葡萄糖4,6-脱水酶活性的酶可以是ATCV-1(SEQ ID NO 40)或者具有至少55％序列同一性的序列的酶。ATCV-1的序列的序列同一性百分比可以改变。序列同一性可以是与SEQ ID NO 40至少55％、60％、65％、70％、75％、80％、85％、90％或95％的同一性。
当宿主含有大量所需要的UDP-糖时，不需要糖核苷酸生物合成酶。
本发明用于产生QA-FRX(X/A)(例如，具有C-28链的QA)的每种方法还可以包括其它步骤：i)包括糖单元以形成C-3链和/或ii)添加糖基化C-18酰基链，如图1所示。
本发明用于产生QA-Tri(R/X)-FRX(X/A)(例如，具有C-3和C-28链的QA)的每种方法还可以包括其它步骤：添加糖基化C-18酰基链，如图1所示。
该方法包括可以处于任何顺序的一些步骤。总之，根据本发明的第一方面，将多种糖链连接至包含QA主链的分子(参见图1)。包含QA主链的分子可以是QA-FRXX、QA-FRXA或者QA-FRXX和QA-FRXA的混合物(即QA-FRX(X/A))。这些步骤的其它详细信息如以下所讨论。
本发明的第四方面是根据SEQ ID NO 2的岩藻糖基转移酶(Qs-28-O-FucT)或者具有至少70％序列同一性的序列的酶。该酶能够以β-键将D-吡喃岩藻糖转移至包含QA的分子的C-28位。这是在本发明的第一方面所述的方法中描述的酶。
Qs-28-O-FucT的序列的序列同一性百分比可以改变。所述序列同一性可以是与SEQ ID NO 2至少70％、75％、80％、85％、90％或95％的同一性。
SEQ ID NO 1的核苷酸或者也编码根据本发明的第四方面的氨基酸的核酸分子编码岩藻糖基转移酶。
本发明的第五方面是根据SEQ ID NO 4的鼠李糖基转移酶(Qs-28-O-RhaT)或者具有至少70％序列同一性的序列的酶。该酶能够以α-1,2-键转移L-吡喃鼠李糖。这是在本发明的第一方面所述的方法中描述的酶。
Qs-28-O-RhaT的序列的序列同一性百分比可以改变。所述序列同一性可以是与SEQ ID NO 4至少70％、75％、80％、85％、90％或95％的同一性。
SEQ ID NO 3的核苷酸或者也编码根据本发明的第五方面的氨基酸的核酸分子编码鼠李糖基转移酶。
本发明的第六方面是根据SEQ ID NO 6的木糖基转移酶(Qs-28-O-XylT3)或者具有至少70％序列同一性的序列的酶。该酶能够以β-1,4-键转移D-吡喃木糖。这是在本发明的第一方面所述的方法中描述的酶。
Qs-28-O-XylT3的序列的序列同一性百分比可以改变。所述序列同一性可以是与SEQ ID NO 6至少70％、75％、80％、85％、90％或95％的同一性。
SEQ ID NO 5的核苷酸或者还编码根据本发明的第六方面的氨基酸的核酸分子编码本发明的木糖基转移酶。
本发明的第七方面是根据SEQ ID NO 8的木糖基转移酶(Qs-28-O-XylT4)或者具有至少70％序列同一性的序列的酶。该酶能够以β-1,3-键转移D-吡喃木糖。
Qs-28-O-XylT4的序列的序列同一性百分比可以改变。所述序列同一性可以是与SEQ ID NO 8至少70％、75％、80％、85％、90％或95％的同一性。
SEQ ID NO 7的核苷酸或者还编码根据本发明的第七方面的氨基酸的核酸分子编码本发明的木糖基转移酶。这是在本发明的第一方面所述的方法中描述的酶。
本发明的第八方面是根据SEQ ID NO 10的芹菜糖基转移酶(Qs-28-O-ApiT4)或者具有至少70％序列同一性的序列的酶。该酶能够以β-1,3-键转移D-呋喃芹菜糖。
序列Qs-28-O-ApiT4的序列同一性百分比可以改变。所述序列同一性可以是与SEQID NO 10至少70％、75％、80％、85％、90％或95％的同一性。
SEQ ID NO 9的核苷酸或者还编码根据本发明的第八方面的氨基酸的核酸分子编码本发明的芹菜糖基转移酶。这是在本发明的第一方面所述的方法中描述的酶。
本发明的第四、第五、第六、第七和第八方面的任何序列同一性百分比可以与本发明的第四、第五、第六、第七和第八方面的任何其它序列同一性百分比组合。
本发明的第九方面是载体，其包含一种或多种编码本发明的第四至第八方面的酶的核酸。所述载体可以包含1、2、3、4或5种编码本发明的第四至第八方面的酶的核酸。优选地，所述载体将包含五种编码本发明的第四至第八方面的酶的核酸或者共同包含这五种核酸的一些载体。任选地，所述载体可以另外包含编码本发明的第二方面的酶的核酸。
本发明的第十方面是宿主细胞，其包含编码本发明的第四至第八方面的酶的核酸，和任选地，编码本发明的第二方面的酶的核酸。
所述宿主细胞可以是植物细胞或微生物细胞。当所述宿主细胞是微生物细胞时，它优选地为酵母细胞。当所述宿主细胞是植物细胞时，所述植物优选地为本氏烟草(Nicotiana benthamiana)。
本发明的第十方面的其它特性在于将本发明的第四至第八方面的核酸和任选地编码本发明的第二方面的酶的核酸引入宿主细胞的方法。可以将所述核酸经由载体引入所述宿主细胞。可以在载体和宿主细胞基因组之间发生重组以将核酸引入宿主细胞基因组。作为另外一种选择，可以通过用多种重组载体共浸润来将所述核酸引入所述宿主细胞。所述重组载体可以是根瘤农杆菌(Agrobacterium tumefaciens)菌株，如以下所讨论的。
本发明的第十一方面是包含如本发明的第十方面所述的宿主细胞的生物系统。所述生物系统可以是植物或微生物。当所述生物系统是植物时，它可以是本氏烟草(Nicotiana benthamiana)或者任何上述植物。产生该植物的方法包括将本发明的核酸引入宿主植物细胞并从经转化的宿主植物细胞再生植物的步骤。当所述生物系统是微生物时，它可以是酵母。
本发明还包括制备根据本发明上述方面的每种酶和每种核酸的方法，以及制备包含一种或多种本发明的核酸的载体的方法，以及制备根据本发明的第十方面的宿主细胞的方法和制备根据本发明的第十一方面的生物系统的方法。这些方法使用了在本领域中熟知的技术和产物，如WO2019/122259和PCT/EP2020/067866(作为WO 2020/260475公开)，并且以下更详细地描述了这些方法。
本发明所述的核酸可以包括在载体，具体地表达载体中，如实施例部分所述。所述载体可以是处于双链或单链的线性或环状形式的任何质粒、粘粒、噬菌体或农杆菌载体，其可以通过整合到细胞基因组或者其它方式转化原核或真核宿主。所述载体可以是表达载体，包括诱导型启动子，其可操作性地连接至所述核酸序列。通常，所述载体可以在诱导型启动子和核酸序列之间包括增强子序列。所述载体还可以包括终止子序列和任选地位于所述终止子序列上游的3'UTR。所述载体可以包括一个或多个编码本发明的第一方面所述的酶的核酸，优选地产生如根据本发明的第一方面所述的分子的一种形式所需的所有序列。所述载体可以是植物载体或微生物载体。
所述载体中的核酸可以受适当的启动子或者用于宿主细胞中的转录的其它调控元件的控制并且可操作性地连接至它们。所述宿主细胞可以是酵母细胞、细菌细胞或植物细胞。所述载体可以是在多种宿主中起作用的双功能表达载体。就基因组DNA而言，这可以含有其自身的启动子或其它调控元件。使用天然启动子的优势在于这可以避免多效性反应。就cDNA来说，这可以受适当的启动子或者用于宿主细胞中的表达的其它调控元件的控制。
对于在植物中使用的优选的载体包含边界序列，其允许表达载体转移并整合到植物基因组中。所述载体可以是植物二元载体。
可以将所述载体转染到任何生物系统中的宿主细胞中。所述宿主可以是微生物，如大肠杆菌(E.coli)或酵母。所述载体可以是根瘤农杆菌(Agrobacterium tumefaciens)菌株的一部分并且可以用于感染生物植物宿主系统。根瘤农杆菌(Agrobacteriumtumefaciens)可以分别包含所需的编码本发明的核酸中的一种，并且可以合并以共感染宿主细胞，从而所述宿主细胞含有所有必需的编码本发明的第一方面的酶的核酸。本发明还包括培养宿主或使宿主生长以用于生产、收获和分离所期望的QA衍生物的步骤。
QA衍生物可能需要进一步合成，如添加C-18酰基链(Wang等人,2005)。为了经由合成方法添加C-18链，可以用3-(叔丁基二甲基甲硅烷氧基)丙醛、顺-2-丁烯、苄基溴、四丁基氟化铵、草酰氯、(R)-2-乙酰氧基-1,1,2-三苯基乙醇、甲氧基钠、叔丁基二甲基甲硅烷基氯化物(TBSCl)、氢、2,3,5-三-O-(叔丁基二甲基甲硅烷基)-L-阿拉伯呋喃糖和氢氧化钡八水合物处理QA衍生物。
制备C-18酰基链的方法包括将3-(叔丁基二甲基甲硅烷氧基)丙醛与顺-2-丁烯合并以制备(3S,4S)-6-{[(叔丁基二甲基)甲硅烷基]氧基}-4-羟基-3-甲基己-1-烯的步骤。然后，与苄基溴合并以制备(3S,4S)-4-(苄基)氧基-6-{[(叔丁基二甲基)甲硅烷基]氧基}-3-甲基-己-1-烯。下一步包括与四丁基氟化铵合并以制备(3S,4S)-4-(苄基)氧基6-羟基-3-甲基己-1-烯，然后与草酰氯合并以形成醛。然后，将醛与(R)-2-乙酰氧基-1,1,2-三苯基乙醇合并，然后与甲氧基钠和TBSCl合并以形成β-甲硅烷氧基甲酯。然后，将β-甲硅烷氧基甲酯与氢合并以制备甲酯。下一步包括将甲酯与2,3,5-三-O-(叔丁基二甲基甲硅烷基)-L-阿拉伯呋喃糖合并以制备阿拉伯糖苷。然后，将阿拉伯糖苷与氢氧化钡八水合物合并以制备酸。下一步包括将酸与先前形成的甲酯合并以制备二酯。然后，将二酯与氢氧化钡八水合物合并以制备酸。这些步骤制备了C-18酰基链。一旦制备了该链，则可以将其添加至C-28糖链。
本发明的第十二方面是根据SEQ ID NO 14(QsAXS1)的UDP-芹菜糖/UDP-木糖合酶或者具有至少70％序列同一性的序列的酶。该酶能够通过提高UDP-α-D-芹菜糖的可用性(当这是限制性的时)来增强芹菜糖基转移酶的活性。
序列QsAXS1的序列同一性百分比可以改变。所述序列同一性可以是与SEQ ID NO14至少70％、75％、80％、85％、90％或95％的同一性。
QsAXS1酶似乎提高了芹菜糖基化产物或木糖基化产物的得率。
例如，芹菜糖基化产物可以是包含QA-TriX/R-FRXA或QA-FRXA的分子。将β-D-芹菜糖连接至另一个糖残基。所述糖残基可以是β-D-木糖残基。所述β-D-木糖残基可以是包含QA-FRX或QA-TriX/R-FRX的分子的一部分。通过根据本发明的第十二方面的酶Qs-28-O-ApiT4(SEQ ID NO 10)和QsAXS1(SEQ ID NO 14)来实施该步骤。
所述木糖基化产物可以是包含QA-TriX/R-FRXX或QA-FRXX的分子。将D-木糖连接至另一个糖残基。所述糖残基可以是β-D-木糖残基。所述β-D-木糖残基可以是包含QA-FRX或QA-TriX/R-FRX的分子的一部分。通过根据本发明的第十二方面的酶Qs-28-O-XylT4(SEQID NO 8)和QsAXS1(SEQ ID NO 14)来实施该步骤。
本发明的第十二方面的其它特性在于编码本发明的第十二方面的酶的核酸分子。
QsAXS1酶可以(例如)通过根据SEQ ID NO 13的核苷酸或者通过借助于简并编码也编码根据本发明的第十二方面的酶的序列所编码。
本发明的每种方法可以包括与如根据本发明的第十二方面所述的酶合并。
本发明的第一方面的其它特性在于在包含QA核心的分子的C-3位制备支链三糖的步骤。所述方法包括将包含QA的分子与UDP-α-D-吡喃葡糖醛酸和酶QsCSL1(SEQ ID NO 26)或者酶QsCslG2(SEQ ID NO 28)合并；与UDP-α-D-吡喃半乳糖和酶Qs-3-O-GalT(SEQ ID NO30)合并；与UDP-β-L-吡喃鼠李糖和酶DN20529_c0_g2_i8(SEQ ID NO 36)或酶Qs_0283850(SEQ ID NO 34)，或者酶Qs-3-O-RhaT/XylT(SEQ ID NO 32)合并；与UDP-α-D-吡喃木糖和酶Qs_0283870(SEQ ID NO 38)或者酶Qs-3-O-RhaT/XylT(SEQ ID NO 32)合并。
在C-3位处制备支链三糖的步骤中所使用的每种酶的序列同一性可以为至少50％、55％、56％、57％、58％、59％、60％、65％、70％或80％。优选地，所述序列同一性为至少90％、95％、96％、97％、98％或99％。
本发明的这种特性涉及制备QA衍生物，如QA-Tri(X/R)的方法，其包括一些步骤。所述步骤可以以特定顺序或以任何顺序或同时进行。优选地，如以下所讨论的，这种衍生物是通过向QA主链连续添加形成C-3链的糖单元所形成的。然后，根据本发明的第一方面并且如图1所述，添加形成C-28四糖链的糖单元。
对于当通过将β-D-吡喃葡糖醛酸残基连接至包含QA的分子以形成包含QA-Mono的分子来起始包含QA核心的分子的C-3位处的支链三糖时的情况，描述了本发明的第一方面的这种特性的步骤。然而，可以以任何顺序发生所述步骤。
优选地实施所述方法，从而可以分离出包含QA-TriX/R的分子或将其进一步衍生化以化学合成下游产物，如QS-21。
本发明所述的方法的一个步骤是将D-吡喃葡糖醛酸连接至包含QA的分子以形成包含QA-Mono的分子。通过酶QsCSL1(SEQ ID NO 26)或者酶QsCslG2(SEQ ID NO 28)实施所述步骤。通过SEQ ID NO 25的核苷酸编码QsCSL1。通过SEQ ID NO 27的核苷酸编码QsCslG2。
本发明所述的方法的另一个步骤是将D-吡喃半乳糖连接至包含QA-Mono的分子上的β-D-吡喃葡糖醛酸残基以形成包含QA-Di的分子。通过酶Qs-3-O-GalT(SEQ ID NO 30)实施所述步骤。通过SEQ ID NO 29的核苷酸编码Qs-3-O-GalT。
本发明所述的方法的其它步骤是将L-吡喃鼠李糖连接至包含QA-Di的分子上的β-D-吡喃葡糖醛酸残基以形成包含QA-TriR的分子。通过酶DN20529_c0_g2_i8(SEQ ID NO36)或者酶Qs_0283850(SEQ ID NO 34)或者酶Qs-3-O-RhaT/XylT(SEQ ID NO 32)实施所述步骤。通过SEQ ID NO 35的核苷酸编码DN20529_c0_g2_i8。通过SEQ ID NO 33的核苷酸编码Qs_0283850。Qs-3-O-RhaT/XylT，它是由SEQ ID NO 31的核苷酸编码的。
本发明所述的方法的还其它步骤包括将β-D-吡喃木糖连接至包含QA-Di的分子上的β-D-吡喃葡糖醛酸残基以形成包含QA-TriX的分子。通过酶Qs_0283870(SEQ ID NO 38)或者酶Qs-3-O-RhaT/XylT(SEQ ID NO 32)实施所述步骤。通过SEQ ID NO 37的核苷酸编码Qs_0283870。通过SEQ ID NO 31的核苷酸编码Qs-3-O-RhaT/XylT。
可以以特定顺序或以任何顺序或同时实施将C-3三糖和C-28四糖链的糖添加至包含QA-核心的分子的步骤。优选地，一旦C-3位处的支链三糖已连接至包含QA核心的分子，则可以将C-28四糖链的糖残基添加至包含QA-TriX、QA-TriR或者QA-TriX和QA-TriR的混合物(即QA-Tri(X/R))的分子，如本发明的第一方面中所述。
本发明的第一方面的其它特性是用于制备QA的方法步骤。所述方法包括将2,3氧化鲨烯与QsbAS(SEQ ID NO 18)合并，与C-28氧化酶QsCYP716-C-28(SEQ ID NO 20)合并，与C-16α氧化酶QsCYP716-C-16α(SEQ ID NO 22)合并和与C-23氧化酶QsCYP714-C-23(SEQID NO 24)合并。
在制备包含QA核心的分子的步骤中所使用的每种酶的序列同一性可以为至少50％、55％、56％、57％、58％、59％、60％、65％、70％或80％。优选地，所述序列同一性为至少90％、95％、96％、97％、98％或99％。
本发明的这种特性涉及制备包含QA核心的分子的方法，其包括一些步骤。所述步骤可以以特定顺序或以任何顺序或同时进行。优选地，如图2所述，通过产生β-香树素骨架，然后分别在C-28、C-16α和C-23位连续氧化来形成该分子。对于上述优选情况描述了本发明的第一方面的这种特性的步骤。然而，可以以任何顺序发生所述步骤。
然后，根据本发明的第一方面并且如图1所述，添加形成C-3三糖和C-28四糖链的糖单元。优选地，制备包含QA核心的分子，然后实施添加C-3链的步骤，随后实施添加C-28四糖链的步骤。然而，可以以特定顺序或以任何顺序或同时实施这些步骤。
本发明所述的方法的一个步骤是2,3氧化鲨烯的环化作用以形成包含三萜β香树素的分子。通过氧化鲨烯环化酶实施该步骤。具体地，氧化鲨烯环化酶是根据QsbAS(SEQ IDNO 18)的酶。通过SEQ ID NO 17的核苷酸编码氧化鲨烯环化酶。
将包含β-香树素骨架的分子分别在C-28、C-16α和C-23位进一步氧化为羧酸、醇和醛。本发明的这种特性的另一个步骤是包含β-香树素骨架的分子的氧化以在C-28位形成羧酸。通过细胞色素P450单加氧酶实施该步骤。细胞色素P450单加氧酶是C-28氧化酶QsCYP716-C-28(SEQ ID NO 20)。通过SEQ ID NO 19的核苷酸编码QsCYP716-C-28。
本发明所述的方法的另一个步骤是包含β-香树素骨架的分子的氧化以在C-16位形成醇。通过细胞色素P450单加氧酶实施该步骤。细胞色素P450单加氧酶是C-16α氧化酶QsCYP716-C-16α(SEQ ID NO 22)。通过SEQ ID NO 21的核苷酸编码QsCYP716-C-16α。
本发明所述的方法的其它步骤是包含β-香树素骨架的分子的氧化以在C-23位形成醛。通过细胞色素P450单加氧酶实施该步骤。细胞色素P450单加氧酶是C-23氧化酶QsCYP714-C-23(SEQ ID NO 24)。通过SEQ ID NO 23的核苷酸编码QsCYP714-C-23。
第一发明的这种特性可以与上述第一发明的任何其它特性组合。
本发明的第一方面的其它特性是QS-21分子的化学合成，其从根据本发明的第一方面的步骤所获得的QA-Tri(X/R)-FRX(X/A)开始并且包括化学添加糖基化的C-18酰基链的其它步骤，如图1所示和在本发明的第一方面所述。将第一发明的这种特性与上述本发明的第一方面的一个或多个其它特性组合。
本发明的第一方面的这种其它特性还可以包括与酶QsFucSyn(SEQ ID NO 12)合并，如本发明的第二方面中所述。它还可以包括与酶QsFucSyn(SEQ ID NO 12)和酶ATCV-1(SEQ.ID No 40)合并，或者它可以包括与酶ATCV-1(SEQ ID NO 40)和具有UDP-4-酮-6-脱氧-葡萄糖4-酮还原酶活性的酶，如QsFSL-1(SEQ ID No.48)、QsFSL-2(SEQ ID No 50)、SoFSL-1(SEQ ID No 52)或者SpolFSL(SEQ ID No 54)合并。
本发明的第一方面的这种其它特性还可以包括与酶QsAXS1(SEQ ID NO 14)合并，如本发明的第十二方面中所述。
本发明的第十三方面是分离的QA衍生物，它是QA-TriX/R-F、QA-TriX/R-FR、QA-TriX/R-FRX、QA-TriX/R-FRXX、QA-TriX/R-FRXA、QA-Mono-F、QA-Mono-FR、QA-Mono-FRX、QA-Mono-FRXX、QA-Mono-FRXA、QA-Di-F、QA-Di-FR、QA-Di-FRX、QA-Di-FRXX或QA-Di-FRXA。当所述分子包含QA-TriX/R-F、QA-TriX/R-FR、QA-TriX/R-FRX、QA-Mono-F、QA-Mono-FR、QA-Mono-FRX、QA-Mono-FRXX、QA-Mono-FRXA、QA-Di-F、QA-Di-FR、QA-Di-FRX、QA-Di-FRXX或QA-Di-FRXA时，所述衍生物还可以包含C-18酰基链。
本发明的其它方面是通过根据本发明的第一方面的方法和本发明的任何方法能够获得或所获得的QA衍生物。
可以从生物系统分离出通过本发明所述的方法所获得的QA衍生物。本发明的其它方面是制备QA衍生物的方法，其包括本发明的方法步骤，包括分离QA衍生物的步骤。
一旦从生物系统分离，则QA衍生物可以用作包括在疫苗组合物中的佐剂。
本发明的QA衍生物可以与其它免疫刺激剂，如TLR4激动剂，具体地脂多糖TLR4激动剂，如脂质A衍生物，特别是单磷酰脂质A，例如，3-脱-O-酰化单磷酰脂质A(3D-MPL)组合。3D-MPL以名称“MPL”由GlaxoSmithKline Biologicals N.A.销售。参见，例如，美国专利号4,436,727；4,877,611；4,866,034和4,912,094。可以根据GB 2 220 211 A中所述的方法产生3D-MPL。在化学上，它是具有4、5或6条酰化链的3-脱酰基单磷酰脂质A的混合物。
可以与本发明的QA衍生物组合的其它TLR4激动剂包括吡喃葡萄糖基脂质佐剂(GLA)，如WO2008/153541或者WO2009/143457或者文献论文(Coler等人2011和Arias等人2012)中所述。
还可以将本发明的佐剂配制到适合的载体，如乳液(例如，水包油乳液)或脂质体中，如以下所描述的。
脂质体
术语“脂质体”在本领域中是熟知的并且定义了包含包围水性空间的一个或多个脂质双分子层的囊泡的一般类别。因此，脂质体由一个或多个脂质和/或磷脂双分子层组成并且可以在它们的结构中含有其它分子，如蛋白质或碳水化合物。由于脂质和水相两者均存在，因此脂质体可以包封或包埋水溶性材料、脂溶性材料和/或两亲性化合物。在WO2013/041572中描述了制备这些脂质体的方法。
基于磷脂组成和用于制备它们的方法，脂质体尺寸可以在30nm至几μm内改变。
脂质体尺寸将在50nm至200nm，特别是60nm至180nm，如70-165nm的范围内。最优地，脂质体应是稳定的并且具有约100nm的直径以允许通过过滤方便的灭菌。
可以通过如测量脂质体的尺寸(Z-均直径，Zav)和多分散性的动态光散射(DLS)或者通过分析脂质体结构的电子显微镜的方法来评价脂质体的结构完整性。平均粒径可以在95nm至120nm之间，和/或多分散性(Pdl)指数可以不大于0.3(如不大于0.2)。
实施例
参考以下非限制性实例描述本发明。
实施例1—鉴定皂皮酸C-28糖基转移酶候选基因
我们产生了6种皂树(Q.saponaria)组织(茎、根和处于4个发育阶段的叶：原基/嫩叶/成熟叶/老叶)的皂树(Q.saponaria)基因组序列数据和RNA-seq数据。该RNA-seq数据集用于注释皂树(Q.saponaria)基因组序列(Earlham Institute,Norwich,Norfolk)。为了鉴定皂树(Q.saponaria)基因组中可能的生物合成基因簇(BGC)，我们使用了PlantiSMASH，它是自动鉴定候选植物BGC的在线平台(Kautsar等人,2017)。这鉴定了一些推定的BGC。预测这些簇中的多种簇参与糖生物合成并且含有家族1UDP-依赖性糖基转移酶(UGT)，一类几乎普遍参与植物特有代谢产物的糖基化的酶。
参与QA-Tri(X/R)的生物合成的生物合成基因主要共有由叶原基中的高表达、老叶中的低表达和其它组织中的中间水平所组成的表达谱。为了鉴定皂皮酸C-28糖基转移酶候选，我们使用自组织映射(SOM)实施共表达分析。对于新候选的鉴定，将皂皮酸(QA)生物合成所需的4种基因(QsbAS以及C-28、C-23和C-16α氧化酶)用作引诱物。基于将它们鉴定为与任何这些引诱物基因共表达的程度，对转录本排列优先次序。这将多种UGT酶鉴定为潜在候选，但是未在不寻常的酶类中鉴定出可能的糖基转移酶基因候选。
先前所鉴定的QS-21生物合成酶在原基中高水平表达。我们对在原基中良好表达的UGT候选进行搜索以鉴定可能不严格共表达但是具有重叠表达谱的候选。在注释为编码UGT的皂树(Q.saponaria)基因组序列中，我们选择了原基组织中RNA-seq表达值为至少30FPKM的序列。我们排除了长度小于400个氨基酸的序列并且对所产生的序列的预测氨基酸序列进行系统发育分析。
为了克隆候选基因，设计了一系列寡核苷酸引物，其在靶标序列上游引入5'attB位点以允许克隆。使用这些引物，通过PCR从皂树(Q.saponaria)叶cDNA扩增基因并克隆到pDONR 207。在转移至植物表达载体pEAQ-HT-DEST1之前，对克隆测序(Sainsbury等人,2009)。然后，将表达构建体单独转化到根瘤农杆菌(Agrobacterium tumefaciens)(LBA4404)中以用于在本氏烟草(N.benthamiana)中瞬时表达。
实施例2-皂皮酸28-O-岩藻糖-酯-转移酶(Qs-28-O-FucT)的鉴定
通过经由酯键连接至皂皮酸骨架C-28位的D-岩藻糖起始C-28直链四糖。在我们的潜在C-28糖基转移酶候选的名单中，我们鉴定了两个岩藻糖基转移酶候选(Ross等人,2011和Sasaki等人,2014)。这些中的一个未被鉴定为与皂皮酸生物合成基因或者在生物合成基因簇内共表达。相反，一个与BGC内的皂皮酸生物合成基因共表达，并且它与已知的三萜羧酸葡萄糖基转移酶更密切相关。
为了筛选岩藻糖基转移酶候选的活性，我们在本氏烟草(N.benthamiana)叶中瞬时共表达了产生QA-Tri(X/R)(皂皮酸C-3三糖的Xylp和Rhap形式两者)所需的基因组。另外，还包括了糙伏毛燕麦(Avena strigosa)HMG-CoA还原酶(AstHMGR)的反馈不敏感型截短形式，因为这先前已显示提高了本氏烟草(N.benthamiana)中产生的三萜的生产。最终，将岩藻糖基转移酶候选与上述基因瞬时共表达。先前在讨论以β-键将D-岩藻糖连接至包含QA的分子的方法步骤时在正文中以及在材料和方法中提供了进一步的详细信息。
浸润的叶提取物的HPLC-CAD-MS分析显示QsUGT_L2具有与将具有D-岩藻糖质量的糖添加至QA-TriX和QA-TriR两者以分别形成QA-TriX-F和QA-TriR-F一致的活性(图5)。QsUGT_L1显示无活性。因此，将QsUGT_L2重新命名为Qs-28-O-FucT。该酶的产物得率极低，预期是由于必需的糖核苷酸辅因子(UDP-α-D-岩藻糖)在本氏烟草(N.benthamiana)中受限(参见实施例6-优化UDP-岩藻糖在本氏烟草(N.benthamiana)中的可用性一节(实施例6))。因此，QA-Tri(X/R)仍是提取物中的主要产物(图5)。
实施例3-皂皮酸28-O-岩藻糖苷[1,2]-鼠李糖基转移酶(Qs-28-O-RhaT)的鉴定
为了鉴定第二种C-28糖基转移酶，将UGT候选在本氏烟草(N.benthamiana)叶中与产生QA-TriX-F所需的基因瞬时共表达。先前在讨论将α-L-鼠李糖连接至β-D-岩藻糖残基的方法步骤时在正文中以及在材料和方法中提供了进一步的详细信息。
HPLC-CAD-MS分析显示一种候选QsUGT_A6的添加导致QA-TriX-F峰的完全减小以及11.6分钟时新的更极性的峰的出现，该峰具有与将鼠李糖添加至QA-TriX-F一致的质量(图6)。在不存在Qs-28-O-FucT的情况下未观察到活性，表明QsUGT_A6的活性取决于Qs-28-O-FucT(6)的岩藻糖基转移酶活性。由于在原基中的高表达，将QsUGT_A6鉴定为候选，如对于制备皂皮酸所需的基因所观察到的，并且另外在相同BGC，簇50(Cluster 50)中将QsUGT_A6鉴定为CSL1和Qs-28-O-FucT。因此，将QsUGT_A6称为Qs-28-O-RhaT。
实施例4—皂皮酸28-O-岩藻糖苷[1,2]-鼠李糖苷[1,4]木糖基转移酶(Qs-28-O-
XylT3)的鉴定
为了搜索在C-28糖链中添加第三糖的糖基转移酶，通过在本氏烟草(N.benthamiana)中与制备QA-TriX-FR所需的基因瞬时共表达，筛选UGT候选的活性。先前在讨论将β-D-木糖连接至α-L-鼠李糖残基的方法步骤时在正文中以及在材料和方法中提供了进一步的详细信息。这表明一种候选QsUGT_A7的添加导致QA-TriX-FR峰的消耗以及极性较低的峰的出现，该峰具有与将木糖添加至QA-TriX-FR一致的质量(图7)。QsUGT_A7的活性取决于Qs-28-O-RhaT的活性，因为没有Qs-28-O-RhaT，QsUGT_A7不能使QA-TriX-F(7)糖基化。由于QsUGT_A7在C-28糖链中添加作为第三糖的木糖，因此将该酶称为Qs-28-O-XylT3。
实施例5-皂皮酸28-O-岩藻糖苷[1,2]-鼠李糖苷[1,4]木糖苷[1,3]木糖基转移酶
和皂皮酸28-O-岩藻糖苷[1,2]-鼠李糖苷[1,4]木糖苷[1,3]芹菜糖基转移酶的鉴定
在此阶段，UDP-α-D-岩藻糖可用性的问题导致在本氏烟草(N.benthamiana)叶中产生了极少量的C-28糖基化产物(图7)。因此，这使得难以对参与C-28糖链中第四步的酶进行筛选，因为不清楚任何新的产物是否将以足以被检测的量产生。为了克服该问题，我们尝试用更大量的D-葡萄糖替换C-28D-岩藻糖，因为这两种糖均具有相同的后续C-28L-鼠李糖所连接的C-2羟基结构。为了实现这种情况，作为Qs-28-O-FucT的替换，测试了来自积雪草(Centella asiatica)的C-28葡萄糖基转移酶CaUGT73AD1(de Costa等人,2017)。
我们在具有生产QA-TriX所需的基因的本氏烟草(N.benthamiana)叶中瞬时共表达了CaUGT73AD1。叶提取物的HPLC-CAD-MS分析显示添加CaUGT73AD1导致在10.1分钟出现新的峰，其质量离子(m/z＝1117)与将葡萄糖添加至QA-TriX以形成QA-TriX-G(MW＝1118.51)一致(图8)。另外，还存在位于11.8分钟处的新的峰，其m/z为1101。先前已观察到通过QsCYP716-C-16α将来自丝石竹皂甙元(Gyp)的三萜骨架转化为皂皮酸在本氏烟草(N.benthamiana)系统中并不总是完整的(WO 2019/122259)。这导致具有代替皂皮酸的丝石竹皂甙元骨架的糖基化中间体的积累。11.8分钟处的新的峰与通过CaUGT73AD1将葡萄糖添加至丝石竹皂甙元三糖Gyp-TriX以形成Gyp-TriX-G(MW＝1102.52)一致(图8)。
然后，我们测试Qs-28-O-RhaT和Qs-28-O-XylT3是否可以利用CaUGT73AD1产物。先前在讨论将β-D-木糖连接至β-D-木糖残基的方法步骤或者将β-D-芹菜糖连接至β-D-木糖残基的方法步骤时在正文中以及在材料和方法中提供了进一步的详细信息。Qs-28-O-RhaT的添加导致10.1分钟处的QA-TriX-G和11.8分钟处的Gyp-TriX-G的峰减小，以及在9.5分钟(m/z＝1263)和11.1分钟(m/z＝1247)处的两个新的更极性的峰的出现，其分别与将鼠李糖添加至QA-TriX-G和Gyp-TriX-G一致(图8)。Qs-28-O-XylT3的进一步添加导致QA-TriX-GR和Gyp-TriX-GR峰减小，以及9.8分钟(m/z＝1395)和11.5分钟(m/z＝1379)处的峰的出现，其与木糖的进一步添加一致(图8)。这表明Qs-28-O-RhaT和Qs-28-O-XylT3能够利用在C-28位具有葡萄糖的三萜糖苷底物。所得的己糖(QA-TriX-GRX和Gyp-TriX-GRX)以足以允许筛选第四C-28糖基转移酶的量积累。
C-28糖链中的最后一步是D-木糖或D-芹菜糖的添加(图4)。在我们的实验中，未发现UDP-α-D-木糖在本氏烟草(N.benthamiana)中受限。然而，就UDP-α-D-岩藻糖来说，我们认为本氏烟草(N.benthamiana)中UDP-α-D-芹菜糖的潜在低水平在鉴定QS-21芹菜糖基转移酶中是潜在的瓶颈。
D-芹菜糖存在于高等植物细胞壁中的果胶多糖鼠李糖聚半乳糖醛酸II(RG-II)中并且在植物细胞壁中交联的形成中起关键性作用。通过双功能酶UDP-芹菜糖/UDP-木糖合酶(AXS)从UDP-α-D-葡糖醛酸合成UDP-α-D-芹菜糖，该酶也产生UDP-α-D-木糖。在本氏烟草(Nicotiana benthamiana)中，通过NbAXS1实施了该活性。NbAXS1的VIGS沉默导致了可能由于RG-II的含芹菜糖侧链中的缺陷所造成的生长缺陷和细胞死亡。UDP-α-D-木糖的水平不受NbAXS1沉默影响，因为UDP-α-D-木糖主要通过高等植物中的UDP-D-葡糖醛酸脱羧酶合成。
不同的AXS所产生的UDP-α-D-芹菜糖和UDP-α-D-木糖之比可以改变：在本氏烟草(N.benthamiana)和拟南芥(A.thaliana)中通过NbAXS1和AtAXS1产生更大量的UDP-α-D-木糖，而就来自欧芹和浮萍(Lemna minor)的AXS来说，主要产生UDP-α-D-芹菜糖，这些植物在次级代谢产物芹菜甙和果胶多糖芹菜糖聚半乳糖醛酸中富含D-芹菜糖。这表明可以在富含芹菜糖的植物中发展出提高的UDP-α-D-芹菜糖生产水平，并且对于含有D-芹菜糖的次级代谢产物，如QS-21的异源生产，本氏烟草(N.benthamiana)中UDP-α-D-芹菜糖的水平可能不足。
皂树(Q.saponaria)基因的自组织映射共表达分析鉴定了与QA基因共表达且在原基中高度表达的'UDP-D-芹菜糖/UDP-D-木糖合酶2'(QsAXS1)，从而表明该基因在QS-21生物合成中可能是重要的。从皂树(Q.saponaria)叶cDNA克隆该基因用于在本氏烟草(N.benthamiana)中共表达。
QsAXS1与生产QA-TriX-GRX和Gyp-TriX-GRX所需的基因的共表达不影响这些产物的积累(图9)。在使用QA-TriX-GRX和Gyp-TriX-GRX作为底物，对于第四C-28糖转移酶的筛选中包括了QsAXS1。筛选内的候选UGT的两种组合改变了所积累的化合物。第一组合是QsUGT_D3的添加，其导致底物峰(QA-TriX-GRX，9.5分钟，m/z＝1395和Gyp-TriX-GRX，11.2分钟，m/z＝1379)的减小和位于9.6分钟(m/z＝1528)和11.5分钟(m/z＝1512)的两个新的峰的积累(图9)。第二组合是两种候选QsUGT_D2和QsUGT_A3的添加，其也导致QA-TriX-GRX和Gyp-TriX-GRX底物峰减小以及9.7分钟(m/z＝1528)和11.6分钟(m/z＝1512)处的新的峰的出现(图9)。在这些组合中积累的新的峰的质量与戊糖(如芹菜糖或木糖)向QA-TriX-GRX和Gyp-TriX-GRX的添加以分别形成QA-TriX-GRX(X/A)(MW＝1528.66)和Gyp-TriX-GRX(X/A)(MW＝1512.66)一致。
我们测试了QsAXS1的添加是否是任何所观察到的活性所必需的。QsUGT_D3显示在不存在QsAXS1的情况下的活性，表明该酶不依赖于QsAXS1活性(图10)。由于已共同筛选了QsUGT_A3和QsUGT_D2，我们单独测试这两种酶以确定哪种酶负责先前所观察到的活性。当在存在或不存在QsAXS1的情况下测试时，QsUGT_A3不显示任何活性，因此我们推断该酶不参与该途径步骤。在存在QsAXS1的情况下，QsUGT_D2是活性的，从而确认该酶作为候选(图10)。在不存在QsAXS1的情况下，QsUGT_D2显示活性大幅降低，转化出极少的前体QA-TriX-GRX和Gyp-TriX-GRX(图10)。
这些结果表明QsUGT_D3是皂皮酸28-O-岩藻糖苷[1,2]-鼠李糖苷[1,4]木糖苷[1,3]木糖基转移酶，因为它不依赖于QsAXS1的活性。UDP-α-d-木糖主要通过UDP-D-葡糖醛酸脱羧酶产生，并且预期AXS的活性不会对本氏烟草(N.benthamiana)中存在的可用的UDP-α-d-木糖库有显著贡献。因此，QsAXS1的添加将影响木糖基转移酶的活性是不太可能的。我们随后将QsUGT_D3称为Qs-28-O-XylT4。
QsUGT_D2的活性取决于与QsAXS1的共表达。这表明QsUGT_D2是芹菜糖基转移酶，因为共表达QsAXS1可以预期影响本氏烟草(N.benthamiana)中可用的UDP-α-D-芹菜糖的水平。我们因此将QsUGT_D2称为Qs-28-O-ApiT4。该结果还表明尽管由于UDP-α-D-芹菜糖在初级代谢中的作用而已知其存在于本氏烟草(N.benthamiana)中，但是通过内源NbAXS1产生的UDP-α-D-芹菜糖的水平对于含有D-芹菜糖的次级代谢产物在本氏烟草(N.benthamiana)中的异源产生是不足的。当异源宿主受限于UDP-α-D-芹菜糖的可用性但产生足够水平的UDP-α-D-葡糖醛酸(如本氏烟草(N.benthamiana))时，与QsAXS1的共表达可以通过将UDP-α-D-葡糖醛酸转化为UDP-α-D-芹菜糖来提高UDP-α-D-芹菜糖的可用性。
实施例6-UDP-岩藻糖在本氏烟草(N.benthamiana)中可用性的优化
A部分：D-岩藻糖的浸润导致在本氏烟草(N.benthamiana)中产生UDP-D-岩藻糖
基于先前在毛地黄中的研究(Faust等人,1994)，预期植物中存在的D-岩藻糖的激活形式是UDP-α-D-岩藻糖。此外，岩藻糖基转移酶Qs-28-O-FucT是UGT，已知它需要UDP-糖作为辅因子。岩藻糖基化化合物相对不良的积累表明相关糖核苷酸(预期是UDP-α-D-岩藻糖)在本氏烟草(N.benthamiana)中明显有限。因此，考虑了加强UDP-α-D-岩藻糖的策略。作为第一策略，实施游离单糖(D-岩藻糖)的外源补充以确定所述糖是否可以被细胞吸收并且被糖补救途径利用以将D-岩藻糖转化为UDP-α-D-岩藻糖。因此，使用无针头注射器将D-岩藻糖溶液(50mM，以及仅有水的对照)浸润到本氏烟草(N.benthamiana)叶中。三天后收获叶并且实施糖核苷酸谱分析。LC-MS/MS分析确定对照(水浸润的)提取物中仅可以检测到单一UDP-脱氧己糖，其对应于UDP-β-L-鼠李糖。相反，可以在D-岩藻糖浸润的叶中检测到两种新的UDP-脱氧己糖产物(图11)。为了确定UDP-α-D-岩藻糖显著存在于植物提取物中，使用如先前所报道的酶促合成方法首先合成了UDP-α-D-岩藻糖标准品(Errey等人,2004)。将该标准品加标到50mM D-岩藻糖浸润的叶提取物中，并且发现与第一个新的峰完全共洗脱，因此确认本氏烟草(N.benthamiana)中UDP-α-D-岩藻糖的存在。未确定第二峰的身份，但是由于本氏烟草(N.benthamiana)中存在的内源C-4差向异构酶的作用，预期是UDP-α-D-喹诺糖(quinovose)(UDP-α-D-岩藻糖的C-4差向异构体)。
在确认可以通过游离D-岩藻糖单糖浸润来加强植物中UDP-α-D-岩藻糖水平后，下一个实验设法确定UDP-α-D-岩藻糖提高的丰度是否改善岩藻糖基化三萜的水平。通过本氏烟草(N.benthamiana)的农杆菌浸润瞬时表达生产岩藻糖基化QA-TriX产物(QA-TriX-F)所必需的基因。在浸润缓冲液中包括50mM D-岩藻糖以加强UDP-α-D-岩藻糖的含量。叶提取物的LC-MS分析显示与仅缓冲液的对照相比，50mM D-岩藻糖浸润的叶中QA-TriX-F产物丰度显著升高(图12)。因此，这表明可以通过提高UDP-α-D-岩藻糖的丰度来实现岩藻糖基化皂苷QA-TriX-F的更高的产量。
B部分：来自非植物种类的NDP-D-岩藻糖生物合成酶的表达
D-岩藻糖的成本将使得该糖的浸润对于大规模皂苷生产不经济。因此，优选地，将在本氏烟草(N.benthamiana)中从内源糖核苷酸库工程化生产D-岩藻糖。尽管在植物中尚不知道D-岩藻糖的生物合成途径，但是基于来自其它生物体的实例，NDP-D-岩藻糖的生物合成的最可能的途径是从NDP-D-葡萄糖开始的两步过程。第一步包括通过NDP-D-葡萄糖4,6-脱水酶催化的NDP-D-葡萄糖向NDP-4-酮-6-脱氧葡萄糖中间体的转化。第二步是由4-酮还原酶(FCD)催化的通过将C-4酮基立体选择性还原为轴向羟基而从NDP-4-酮-6-脱氧葡萄糖形成NDP-D-岩藻糖(图)。
我们因此尝试鉴定和瞬时表达先前表征的可以实现这两种活性的酶并且确定它们对本氏烟草(N.benthamiana)中岩藻糖基化皂苷的得率的影响。这两步中的第一步对于NDP-D-岩藻糖和NDP-L-鼠李糖生物合成两者是常见的，并因此应在本氏烟草(N.benthamiana)中产生4-酮-6-脱氧葡萄糖中间体。然而，在高等植物中4,6-脱水酶不作为单独的酶存在，而是作为较大的鼠李糖合酶(RHM)的一部分存在，在该鼠李糖合酶中4,6-脱水酶、3,5-差向异构酶和4-酮-还原酶以单一酶存在。因此，我们选择来自刺胞虫小球藻病毒1(ATCV-1)的UDP-D-葡萄糖4,6-脱水酶，它已知从UDP-D-葡萄糖产生UDP-4-酮-6-脱氧葡萄糖。对于第二FCD步骤，唯一已知的酶来自D-岩藻糖产生细菌，包括伴放线放线杆菌(Aggregatibacter actinomycetemcomitans)、喜温无氧芽孢杆菌(Anoxybacillustepidamans)、大肠杆菌(Echerichia coli)和灰黄链霉菌(Streptomyces griseoflavus)。如在植物中所观察到的，预期这些细菌酶利用dTDP-糖而不是UDP糖。因此，为了提高鉴定功能性酶的概率，选择来自伴放线放线杆菌(A.actinomycetemcomitans)、喜温无氧芽孢杆菌(A.tepidamans)和大肠杆菌(E.coli)的FCD酶(分别为AaFCD、AtFCD和EcFCD)用于瞬时表达。
在本氏烟草(N.benthamiana)中瞬时表达4种酶(ATCV-1和三种FCD基因)中的每一种以及生产QA-TriX-F产物所必需的基因组(AstHMGR、QsbAS、QsCYP716-C-28+QsCYP716-C-16α+QsCYP714-C-23+QsCSL1+Qs-3-O-GalT+Qs_0283870+Qs-28-O-FucT)。我们观察到与对照相比，所述酶中的每一种能够为QA-TriX-F产物提供小幅加强，并且积累的量与通过50mMD-岩藻糖浸润所产生的量相当(图14)。这些结果表明可能经由本氏烟草(N.benthamiana)中与细菌中所鉴定途径类似的途径进行UDP-D-岩藻糖生物合成，并且ATCV-1酶或者FCD酶能够利用本氏烟草(N.benthamiana)中的内源代谢产物以增强UDP-D-岩藻糖的水平。最终，将ATCV-1酶与AaFCD共表达以观察是否可以进一步增强产物得率。然而，相对于任一种单独的酶，该方法似乎对QA-TriX-F生产影响很小(图15)。这些结果证实有可能通过UDP-D-葡萄糖4,6-脱水酶(ATCV-1)或者细菌4-酮还原酶(FCD)的共表达并且不必需包括额外的D-岩藻糖来提高本氏烟草(N.benthamiana)中岩藻糖基化皂苷的含量。
C部分：来自皂树(Q.saponaria)的岩藻糖-加强酶的鉴定和C-28糖苷的纯化
尽管D-岩藻糖的共浸润或者NDP-D-岩藻糖生物合成酶的共表达两者都导致岩藻糖基化产物产量加强，但是非岩藻糖基化前体(QA-Tri)的相对转化仍相对不良(参见图14A)，表明UDP-D-岩藻糖可能仍是受限的并且提示进一步尝试研究D-岩藻糖生产。因此，实施了在皂树(Q.saponaria)中UDP-α-D-岩藻糖可能的生物合成的研究。先前描述的BGC簇‘50’含有与QS-21生物合成相关的一些基因，包括C-16氧化酶、QsCSL1基因(GlcpAT)、Qs28-O-RhaT和Qs-28-O-FucT，加上一些未知功能的基因。在这些未知基因中，发现存在注释为短链脱氢酶/还原酶超家族(SDR)成员的氧化还原酶。大部分已知的糖核苷酸互变酶(NSE)负责QS-21中存在的多种UDP-糖的生物合成，它们也是SDR超家族的成员。因此，克隆所述酶，并将其在具有生产QA-TriR-F产物(在C-3三糖内具有鼠李糖的变体)所必需的成套基因的本氏烟草(N.benthamiana)中瞬时表达。成簇的SDR的包含导致QA-TriR-F产物的量显著升高，表明SDR能够增强岩藻糖基转移酶的活性。因此，此后将SDR称为QsFucSyn。必需包括Qs-28-O-FucT和QsFucSyn酶两者以获得QA-TriR-F产物的大幅提高。
然后，使用QA-TriR骨架，逐步合成C-28四糖链以验证QsFucSyn酶对于化合物生产的重要性。在每种情况下，产物丰度比较显示QsFucSyn酶对于加强C-28糖基化产物含量是重要的(图18)。使用QsFucSyn酶，确认了具有末端木糖或末端芹菜糖的全部C-28糖苷的生产(图19)。
最终，再次确定了QsAXS1酶对于加强芹菜糖基化产物得率的重要性。在存在或不存在QsAXS1酶的情况下实施了用于生产QA-TriR-FRXA的酶的瞬时表达。EIC分析确认在不存在QsAXS1的情况下仅可以检测少量QA-TriR-FRXA产物(MW＝1526.68)，其中共洗脱前体QA-TriR-FRX(MW＝1394.64)中的大部分保留在11.6min处的样品中(图20)。相反，QsAXS1的包含导致QA-TriR-FRXA产物数倍增加以成为11.6分钟处的主要产物。
在鉴定五种糖转移酶和增强C-28糖基化产物生产所必需的关键QsAXS1/QsFucSyn酶之后，我们对使用QA-TriR骨架生产C-28四糖链的每个步骤实施了如前所述的大规模真空浸润(Reed等人,2017，Stephenson等人,2018)，以纯化足够量的每种靶化合物(QA-TriR-F、QA-TriR-FR、QA-TriR-FRX、QA-TriR-FRXX和QA-TriR-FRXA)用于NMR分析。
NMR分析确认QA-TriR-F的结构为皂皮酸3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-[β-D-吡喃岩藻糖基](图26)；QA-TriR-FR为皂皮酸3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基}(图27)；QA-TriR-FRX为皂皮酸3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基}(图28)；QA-TriR-FRXX为皂皮酸3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基}(图29)；和QA-TriR-FRXA为皂皮酸3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-呋喃芹菜糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基}(图30)。
D部分：通过ATCV-1的共表达进一步增强QsFucSyn的活性
QsFucSyn酶与一些从其它物种表征的SDR酶有关，包括来自罂粟属植物的沙罗泰里啶还原酶(56％氨基酸同一性)、来自辣椒(Capsicum annuum)(57％同一性)和胡椒薄荷(Mentha pipertia)(55％同一性)的新薄荷醇脱氢酶以及来自拟南芥(Arabidopsisthaliana)的两种醛还原酶(两者均为61％的同一性)。这些酶的底物是不同的，然而可以看出在每种情况下，所述酶催化羰基还原为醇。所提议的从UDP-D-葡萄糖生物合成UDP-D-岩藻糖的第二步包括在C-4位的酮还原(图15)。有可能的是一旦UDP-4-酮-6-脱氧-D-葡萄糖已添加至QA主链，则QsFucSyn酶在UDP-4-酮-6-脱氧-D-葡萄糖(作为UDP-L-鼠李糖生物合成中中间体的天然存在的产物)的C-4处实施立体选择性还原。作为另外一种选择，QsFucSyn酶可以在UDP-4-酮-6-脱氧-D-葡萄糖的C-4处实施立体选择性还原以形成UDP-D-岩藻糖。考虑该原因，可以预期提高UDP-4-酮-6-脱氧-D-葡萄糖在本氏烟草(N.benthamiana)中的可用性将进一步增强QsFucSyn酶的活性。先前描述的ATCV-1酶是UDP-D-葡萄糖4,6-脱水酶(UGD)并且从UDP-d-葡萄糖产生UDP-4-酮-6-脱氧-D-葡萄糖(Parakkottil Chothi等人,2010)。
因此，为了测试ATCV-1是否可以增强QsFucSyn的活性，将这两种酶与一组生产QA-TriR-F产物所必需的酶瞬时共表达。测量了叶提取物中QA-TriR-F的水平，并将其用于确定该策略的有效性。如所预期的，相对于任一种单独的策略的表达，ATCV-1和QsFucSyn两者的组合增强了QA-TriR-F产物的水平(图21)。QA-TriR-F产物的增加伴随着QA-TriR水平的降低，表明所述提高是岩藻糖基化提高的直接结果。这证实UDP-D-葡萄糖4,6脱水酶与QsFucSyn的共表达是增强岩藻糖基化皂苷生产的有效策略。这可以通过类似于ATCV-1的酶(具有独立的4,6-脱水酶活性)实现。作为另外一种选择，可以通过植物UDP-L-鼠李糖合酶的截短来产生这种酶。这些酶通常在经由具有4,6-脱水酶、3,5-差向异构酶和4-还原酶活性的单一大型酶所实施的3-步反应中将UDP-D-葡萄糖转化为UDP-L-鼠李糖。然而，通过RHM蛋白的N-末端编码4,6-脱水酶活性并且4,6-脱水酶可以从后两步分离。通过利用拟南芥(Arabidopsis thaliana)RHM2基因(AT1G53500，通常667个氨基酸长)的截短变体，观察到这种情况的实例。从C-末端除去297个氨基酸以留下N末端370个氨基酸导致产生了仅具有UDP-d-葡萄糖4,6-脱水酶活性的功能蛋白。这种截短变体与ATCV-1具有60％的同一性。因此，截短的RHM基因的使用可能是ATCV-1的可行的替代。
E部分：FucSyn同源物的鉴定
为了研究QsFucSyn的特异性，研究了其它同源物。首先，皂树(Q.saponaria)基因组的分析显示在氨基酸水平上在52％-91％同一性范围内的15个同源物。转录组分析显示这些中的大部分具有极低的FPKM表达值，表明所述酶可能是假基因产生的。然而，一些的确似乎在不同组织中以不同程度表达。因此，克隆两种这种候选以研究它们的FucSyn-样活性。将它们命名为QsFucSyn-样(QsFSL)。QsFucSyn-样表示在氨基酸水平上与QsFucSyn具有52％-91％同一性的候选。第一(QsFSL-1)在氨基酸水平上与FucSyn具有82％的同一性，并且第二(QsFSL-2)具有54％的同一性。然后，我们研究了肥皂草(Saponaria officinalis，通俗称为肥皂草并且是不相关的石竹科(Caryophyllaceae)成员)中的QsFucSyn-样蛋白。已知肥皂草(S.officinalis)产生D-岩藻糖基化皂苷，因此在该植物中鉴定了QsFucSyn的同源物(称为SoFSL-1)。通过PCR从它们各自植物的cDNA扩增所有基因，克隆到pEAQ-HT-DEST1中并转化到根瘤农杆菌(A.tumefaciens)中用于在本氏烟草(N.benthamiana)中瞬时表达。将用于生产QA-TriR-F产物的基因组瞬时共表达。另外，还共表达了多种FSL并且使用LC-CAD测量了对QA-TriR-F产生的影响(图22)。
分析显示所有所测试的FSL基因导致岩藻糖基化产物相对于阴性对照至少两倍升高，尽管原始QsFucSyn导致了最强的升高。这提供了与QsFucSyn具有同源性的蛋白还可以是增强岩藻糖基化的有用工具的强有力证据。QsFucSyn、QsFSL-1、QsFSL-2和SoFSL-1的系统发育分析显示这些蛋白可能形成SDR114C家族的一部分(图23)。
然后，研究了菠菜(Spinacia oleracea)中的QsFucSyn-样蛋白。SOAP6是D-岩藻糖基转移酶并且参与菠菜(Spinacia oleracea)中皂苷(yossoside)的生物合成。SOAP6催化苜蓿酸-3-O-GlcA的C-28D-岩藻糖基化以形成产物“Yossoside I”(Jozwiak,2020)(图24)。已注意到当在本氏烟草(N.benthamiana)中瞬时表达时SOAP6的功能可能受损，从而导致Yossoside I的有限积累。这可能是由于必需的糖核苷酸前体(即UDP D-岩藻糖)的有限可用性所造成的。
Yossoside基因显示，通过使用早期途径基因(SOAP1、SOAP2和CYP716A268v2)作为引诱物实施共表达分析能够实现强共表达和发现已知的Yossoside途径酶(Jozwiak,2020)。这种共表达分析的产出物含有大于1000个来自菠菜的基因(Jozwiak,2020)。尽管原始研究未鉴定参与D-岩藻糖生物合成的任何FucSyn-样酶，但是分析了共表达数据的与QsFucSyn有关的SDR的存在。在该数据集中发现了单个实例，其中针对SOAP1和CYP716A268v2的共表达值大于0.9。该酶在本文中被称为菠菜(Spinacia oleracea)FucSyn-样(SpolFSL)。
通过PCR从菠菜克隆了SpolFSL以及来自生产Yossoside I所必需的yossoside途径的一些其它基因。Yossoside生物合成的早期步骤包括β-香树素合酶(SOAP1)和C-28氧化酶(SOAP2/CYP716A268)(图24)。由于皂树皂苷生物合成也有这些步骤，因此仅克隆了yossoside-特异性酶，包括C-2β氧化酶(SOAP3/CYP72A655)、C-23氧化酶(SOAP4/CYP72A654)、C-3葡糖醛酸基转移酶(SOAP5)和C-28D-岩藻糖基转移酶(SOAP6)。将这些yossoside基因与皂树β-香树素合酶(QsbAS)和C-28氧化酶(QsCYP716-C-28)一起在本氏烟草(N.benthamiana)中瞬时共表达。通过LC-MS的后续分析确认可以在本氏烟草(N.benthamiana)中检测出Yossoside I并且其存在取决于SOAP6的存在(图24)。此外，SpolFSL的包含导致Yossoside I产物显著增加(图24)，表明类似于QsFucSyn酶，SpolFSL可能参与D-岩藻糖基化。类似地，QsFucSyn的包含还导致Yossoside I的增加。
在证实SpolFSL酶能够加强Yossoside I产物后，研究了SpolFSL加强非菠菜D-岩藻糖基化产物的能力。在本氏烟草(N.benthamiana)中瞬时表达了生产QA-TriR-F所需的酶。已发现与仅QA-TriR-F酶(即无FSL)的对照相比，SpolFSL酶的共表达显著提高了QA-TriR-F的量。QA-TriR-F的加强水平与通过来自不同物种的一些其它FucSyn-样酶所实现的加强相当，包括皂树(Quillaja Saponaria)FucSyn(QsFucSyn)、FucSyn-样1(QsFSL-1)和FucSyn-样2(QsFSL-2)酶以及肥皂草(Saponaria officinalis)FucSyn-样(SoFSL)(图25)。图25中显示了成对的同一性(蛋白)。总体上，这些结果证实了来自整个植物界的FucSyn-样蛋白加强D-岩藻糖基化产物水平的能力。
材料和方法
引物和克隆
通过PCR从来源于皂树(Q.saponaria)的叶组织的cDNA扩增了编码本文所描述的酶(Qs-28-O-FucT、Qs-28-O-RhaT、Qs-28-O-XylT3、Qs-28-O-XylT4、Qs-28-O-ApiT4、QsFucSyn、QsFSL-1、QsFSL-2、SoFSL-1和QsAXS1)的基因。使用表1中详细描述的引物和iProof聚合酶，通过根据生产商的建议的热循环进行PCR。纯化所产生的PCR产物(QiagenPCR纯化试剂盒)并根据生产商的说明书，使用BP clonase将每个产物克隆到pDONR207载体中。将BP反应转化到大肠杆菌(E.coli)中，并培养所得的转化体，并通过miniprep(Qiagen)分离质粒。对分离的质粒测序(Eurofins)以验证正确基因的存在。然后，使用LR clonase将三种基因中的每一种进一步亚克隆到pEAQ-HT-DEST1表达载体中。通过在液氮中闪冻，将所得载体用于转化根瘤农杆菌(A.tumefaciens)LBA4404。
表1用于克隆序列的引物。以黑色显示了基因特异性序列，而以灰色显示了克隆所需的attB位点。
本氏烟草(N.benthamiana)叶的农杆菌浸润
如前所述，使用无针头注射器进行农杆菌浸润(Reed等人,2017)。如上所述，在根瘤农杆菌(A.tumefaciens)LBA4404中由pEAQ-HT-DEST1二元表达载体表达出所有基因(Sainsbury等人,2009)。细菌和植物的培养如(Reed等人,2017)所述。
用于LC-MS分析的本氏烟草(N.benthamiana)叶提取物的制备
在农杆菌浸润后5天收获叶并冻干。用钨珠，以1000rpm破坏干燥叶材料(10mg/样品)1min(Geno/Grinder 2010,Spex SamplePrep)。在550μL含有20μg/mL内标(洋地黄毒苷(Sigma-Aldrich))的80％甲醇中提取代谢产物并在18℃培育20min，同时以1400rpm振荡(Thermomixer Comfort,Eppendorf)。通过用400μL己烷分配两次来使每个样品脱脂。弃去上层的相，并将下层的水相在40℃真空干燥1小时(EZ-2系列蒸发器，Genevac)。将干燥材料在75μL 100％甲醇中再次悬浮并以12,500×g过滤30秒(0.2μm,Spin-X,Costar)。将滤液(50μL)与50μL 50％甲醇在玻璃小瓶中结合并如下详细描述进行分析。
本氏烟草(N.benthamiana)叶提取物的HPLC-CAD-MS分析
使用配备有单四极杆质谱LCMS-2020(Shimadzu)和Corona Veo RS荷电气溶胶检测器(CAD)(Dionex)的Shimadzu Prominence HPLC系统进行分析。检测：MS(双重ESI/APCI电离，脱溶剂曲线温度＝250℃，雾化气流＝15L.min-1，加热块温度＝400℃，正喷雾电压4.5kV，负喷雾电压-3.5kV)，CAD数据采集率10Hz，过滤常数3.6s，925蒸发器温度35℃，离子阱电压20.5V。方法：溶剂A：[H2O+0.1％甲酸]溶剂B：[乙腈(CH3CN)+0.1％甲酸]。进样体积：10μL。梯度：15％[B]，从0至1.5min；15％至60％[B]，从1.5至26min；60％至100％[B]，从26至26.5min；100％[B]，从26.5至28.5min；100％至15％[B]，从28.5至29min；35％[B]，从29至30min。使用0.3mL.min-1的流速和Kinetex柱2.6μm XB-C18 50×2.1mm(Phenomenex)实施方法。使用LabSolutions软件(Shimadzu)进行分析。当进行QA-TriR和QA-TriR-F产物定量时，在CAD迹线中测量产物的峰面积并除以内标(洋地黄毒苷)的峰面积。
本氏烟草(N.benthamiana)的大规模真空浸润
如前所述(Reed等人,2017，Stephenson等人,2018)，使用携带有具有如表2所详细描述的相关基因的pEAQ-HT-DEST1表达载体的根瘤农杆菌(A.tumefaciens)LBA4404菌株，来真空浸润植物。5天后收获植物并将叶冻干。
来自本氏烟草(N.benthamiana)大规模浸润的化合物的纯化
用于提取和快速色谱法的有机溶剂是试剂等级的并且未进一步蒸馏就直接使用。通过己烷初始提取来自大规模浸润的干燥叶材料以脱脂，然后在95℃回流下使用甲醇/水(对于QA-TriR-F和QA-TriR-FR为90/10，并且对于QA-TriR-FRX、QA-TriR-FRXX和QA-TriR-FRXA为80/20)连续极限抽提，持续2天。合并粗甲醇提取物并减压蒸发并重新溶解在最少量的甲醇中，并通过等体积的水稀释，然后使用分离漏斗对己烷、二氯甲烷、乙酸乙酯和正丁醇进行分配。重新收集丁醇层并减压蒸发，并重新溶解在最少量的甲醇中并用冷丙酮饱和以沉淀富集皂苷的粗级分。使用Phenomenex Luna C18柱(对于制备色谱和半制备色谱分别为250×21.2和250×10mm i.d.；5μm)，以含有0.1％甲酸的水/乙腈洗脱液系统，以下列化合物-特异的条件，对该级分进行反相制备色谱纯化：对于QA-TriR-F，在Agilent半制备C18-HPLC上分离该级分[(梯度，35min内90/10→30/70，3mL/min)，(等度的60:40，1mL/min)]；对于QA-TriR-FR和QA-TriR-FRX，除了以下梯度外如对于QA-TriR-F一样分离所述级分：在50min内90/10→30/70，3mL/min；对于QA-TriR-FRXX，以如下梯度在Agilent制备C18-HPLC上分离该级分：17min内90/10→30/70，25mL/min；并且对于QA-TriR-FRXA，在制备和半制备C18-HPLC上分离该级分(以梯度：在17min内90/10→30/70，25mL/min和30min内等度的60/40，2mL/min)。表2中详细说明了干燥叶重量和每种分离的化合物的纯化量。
NMR分析
在配备有BBFO Plus Smart探针和三重共振TCI冷冻探针(JIC,UK)的BrukerAvance 600MHz光谱仪上分别记录1D和2D NMR光谱。化学位移是相对于残留信号溶剂(MeOH-d4:δH 3.31；δC 49.15)。
表2用于大规模真空浸润的菌株、浸润植物数、干燥叶重量和每种化合物所纯化的产物的量。
UDP-α-D-岩藻糖标准品的合成
如前所述(Errey等人,2004)，使用一锅酶促程序进行UDP-α-D-岩藻糖标准品的制备。简要地，将丙酮酸激酶(50U)、无机磷酸酶(5U)、半乳糖-1-磷酸尿甙基转化酶(75U)、葡糖-1-磷酸尿甙基转化酶(5U)和半乳糖激酶(100U)在含有UTP(2mg/mL)、ATP(0.1mg/mL)、PEP(1.4mg/mL)、UDP-α-D-葡萄糖(0.1mg/mL)和D-岩藻糖(1mg/mL)的缓冲液(50mM HEPES，pH 8.0，5mM KCl、10mM MgCl2)中合并。将反应(总体积1mL)在室温下保持过夜。次日，如以下详细描述的，通过HPLC进行UDP-α-D-岩藻糖的纯化。
用甲醇1:1稀释样品，并上样至Poros HQ 50柱(50×10mm，柱体积(CV)＝3.9mL)。以8ml/min的流速，用5CV的5mM NH4HCO3缓冲液平衡柱。样品进样后，如下运行线性梯度(8mL/min)：溶剂A[5mM NH4HCO3]，溶剂B[250mM NH4HCO3]。梯度：15CV内0％[B]至100％[B]，并且保持5CV。在每次运行之间，将柱在100％[B]中平衡另外3CV。通过在265nm监测吸收，进行UDP-α-D-岩藻糖的检测。
通过高分辨质谱和1H NMR确认UDP-α-D-岩藻糖的身份，并根据文献(Errey等人,2004)查找。
从本氏烟草(N.benthamiana)叶提取糖核苷酸
用50mM D-岩藻糖(Glycon Biochemicals)的溶液或水浸润本氏烟草(N.benthamiana)植物(约6周大)的叶。2天后，收获浸润的叶，并将2g叶材料在液氮中闪冻。将叶加标2μg内标(UDP-2-乙酰氨基-2-脱氧-α-D-葡糖醛酸(UDP-GlcNAcA))并使用研钵及研杵研磨成细粉。添加氟化钠溶液(10mL，40mM)并将样品在冰上培育1小时，并不时振荡/涡旋并进行三个超声循环(每个60秒，4℃)。将样品以29,000×g在4℃离心20min，并将上清液转移到玻璃圆底烧瓶中，冷冻并冻干过夜。次日，将样品溶于9％的丁-1-醇水溶液(6mL)中并用90％的丁-1-醇(2mL)提取。将样品在4℃以2000×g离心10min以辅助各层分离，其中每次弃去上部有机层。为了完全除去亲脂性化合物，将提取重复3次。合并下部水层并转移到梨形烧瓶中，冷冻并冻干过夜。将干燥样品溶于500μL碳酸氢铵(5mM)并如前所述，使用固相提取(SPE)(SupelClean ENVI-Carb SPE管,250mg)提取糖核苷酸(等人,2001)。
简要地，用80％乙腈和0.1％三氟乙酸的溶液(3mL)，然后用水(2mL)平衡柱。将样品加载到柱上以吸附糖核苷酸并用水(2mL)随后用25％乙腈(2mL)和50mM三乙基乙酸铵(TEAA)缓冲液pH 7.0(2mL)清洗柱。最终，用25％乙腈在50mM TEAA缓冲液，pH 7.0(1.5mL)中的溶液洗脱糖核苷酸。通过0.45μm PTFE盘式过滤器过滤样品，冷冻并冻干。如以下详细描述的，在通过LC-MS分析之前，将样品溶于具有NH4OH(50μL，5mM)的0.3％甲酸溶液，pH9.0。使用浓度为10μM的糖核苷酸标准品。
本氏烟草(N.benthamiana)叶提取物的糖核苷酸谱分析
如(Rejzek等人,2017)中详细描述的，进行糖核苷酸的分析。简要地，使用处于负离子模式(毛细管电压1.5kV，500℃脱溶剂温度，1000L/h脱溶剂气体，150L/h进样锥气体和7巴雾化器压力)的Waters Xevo TQ-S系统进行ESI-MS/MS分析。使用ThermoFisherHypercarbTM柱(1×100mm，粒径3μm)，以80μL/min的流速以及下列流动相实施色谱法：溶剂A[0.3％甲酸，pH 9.0，具有NH4OH]，溶剂B[乙腈]。梯度：2％[B]至15％[B]，从0至20min；15％[B]至50％[B]，从20min至26min；50％[B]至90％[B]，从26min至27min，并且在90％[B]保持直至30min。从90％[B]至2％[B]从30min至31min重新平衡该柱并且在2％[B]保持直至50min。
菠菜基因的引物和克隆
菠菜种子购自当地园艺中心(Norwich,UK)并在秧苗堆肥上播种并在22℃萌发。在约两周大时收获叶，并使用Plant RNeasy试剂盒(Qiagen)提取RNA并将其用于cDNA的合成。使用如表3详细描述的引物进行yossoside生物合成基因SOAP3-6和SpolFSL的克隆。如“引物和克隆”以及“本氏烟草(N.benthamiana)叶的农杆菌浸润”中所述，将基因克隆到二元表达载体pEAQ-HT-DEST1中并转化到根瘤农杆菌(A.tumefaciens)LBA4404中。如“本氏烟草(N.benthamiana)叶提取物的HPLC-CAD-MS”节中详细描述的，实施瞬时表达和LC-MS/CAD分析。通过CAD测量感兴趣的化合物的峰面积并除以内标(洋地黄毒苷1.1mg/g每干燥叶重量)的峰来定量峰。然后，将来自所有重复(n＝3)的调整的峰面积取平均值。使用ClustalOmega(v 1.2.4)计算成对的序列同一性百分比。
引物
表3：用于克隆菠菜基因的引物。以黑色显示了基因特异性序列，而以灰色显示了克隆所需的attB位点。
缩写
AaFCD—伴放线放线杆菌(Aggregatibacter actinomycetemcomitans)NDP-4-酮-6-脱氧葡萄糖4-酮还原酶
Apif—D-呋喃芹菜糖
Araf—L-呋喃阿拉伯糖
AstHMGR—糙伏毛燕麦(Avena strigosa)截短的3-羟基-3-甲基-戊二酰-CoA还原酶
ATCV-1—刺胞虫(Acanthocystis turfacea)小球藻病毒1UDP-D-葡萄糖4,6-脱水酶
AtFCD—喜温无氧芽孢杆菌(Anoxybacillus tepidamans)NDP-4-酮-6-脱氧葡萄糖4-酮还原酶
DN20529_c0_g2_i8—皂树(Q.saponaria)QA-Diα-1,3-L-鼠李糖基转移酶
EcFCD—大肠杆菌(Echerichia coli)NDP-4-酮-6-脱氧葡萄糖4-酮还原酶
FR—β-D-岩藻糖和α-L-鼠李糖的二糖
FRX—β-D-岩藻糖、α-L-鼠李糖和β-D-木糖的三糖
FRXX—β-D-岩藻糖、α-L-鼠李糖和两个β-D-木糖的四糖
FRXA—β-D-岩藻糖、α-L-鼠李糖、β-D-木糖和β-D-芹菜糖的四糖
FRXX/A—作为FRXX或FRXA的四糖
Fucp—D-吡喃岩藻糖
FucSyn—加强岩藻糖基化皂苷生产的酶
FSL—FucSyn-样
Galp—D-吡喃半乳糖
GlcpA—D-吡喃葡糖醛酸
Glcp—D-吡喃葡萄糖
Gyp—丝石竹酸
Gyp-TriX-G—3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃葡萄糖酯}-丝石竹酸
Gyp-TriX-GR—3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃葡萄糖基酯}-丝石竹酸
Gyp-TriX-GRX—3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃葡萄糖基酯}-丝石竹酸
NSE—糖核苷酸互变酶
OS—2,3-氧化鲨烯
OSC—氧化鲨烯环化酶
QA—皂皮酸
QA衍生物
-QA-Di—3-O-{β-D-吡喃半乳糖基-(1->2)-β-D-吡喃葡糖苷酸}-皂皮酸
-QA-Di-F—3-O-{β-D-吡喃半乳糖基-(1->2)-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-Di-FR—3-O-{β-D-吡喃半乳糖基-(1->2)-β-D-吡喃葡糖苷酸}-28-O-{α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-Di-FRX—3-O-{β-D-吡喃半乳糖基-(1->2)-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-Di-FRXA—3-O-{β-D-吡喃半乳糖基-(1->2)-β-D-吡喃葡糖苷酸}-28-O-{β-D-呋喃芹菜糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-Di-FRXX—3-O-{β-D-吡喃半乳糖基-(1->2)-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-Mono—3-O-{β-D-吡喃葡糖苷酸}-皂皮酸
-QA-Mono-F—3-O-{β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-Mono-FR—3-O-{β-D-吡喃葡糖苷酸}-28-O-{α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-Mono-FRX—3-O-{β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-Mono-FRXA—3-O-{β-D-吡喃葡糖苷酸}-28-O-{β-D-呋喃芹菜糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-Mono-FRXX—3-O-{β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-TriR—3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-皂皮酸
-QA-TriR-F—3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-TriR-FR—3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-TriR-FRX—3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-TriR-FRXA—3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-呋喃芹菜糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-TriR-FRXX—3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-TriX—3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-皂皮酸
-QA-TriX-F—3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-TriX-FR—3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-TriX-FRX—3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-TriX-FRXA—3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-呋喃芹菜糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-TriX-FRXX—3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸
-QA-TriX-G—3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃葡萄糖基酯}-皂皮酸
-QA-TriX-GR—3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃葡萄糖基酯}-皂皮酸
-QA-TriX-GRX—3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃葡萄糖基酯}-皂皮酸
-QA-Tri(X/R)—在C-3位被支链三糖糖基化的QA，它是QA-TriX或QA-TriR
-QA-Tri(X/R)-F—在C-28和C-3位糖基化的QA，它是QA-TriX-F或QA-TriR-F
-QA-Tri(X/R)-FR—在C-28和C-3位糖基化的QA，它是QA-TriX-FR或QA-TriR-FR
-QA-Tri(X/R)-FRX—在C-28和C-3位糖基化的QA，它是QA-TriX-FRX或QA-TriR-FRX
-QA-Tri(X/R)-FRXA—在C-28和C-3位糖基化的QA，它是QA-TriX-FRXA或QA-TriR-FRXA
-QA-Tri(X/R)-FRXX—在C-28和C-3位糖基化的QA，它是QA-TriX-FRXX或QA-TriR-FRXX
-QA-Tri(X/R)-FRX(X/A)—在C-28和C-3位糖基化的QA，它是QA-TriX-FRXX、QA-TriX-FRXA、QA-TriR-FRXX或QA-TriR-FRXA
-QA-F—在C-28位单糖基化的QA。
-QA-FR—在C-28位二糖基化的QA。
-QA-FRX—在C-28位三糖基化的QA。
-QA-FRXA—在C-28位四糖基化的QA。
-QA-FRXX—在C-28位四糖基化的QA。
-QA-FRX(X/A)—在C-28位糖基化的QA，它是QA-FRXX或QA-FRXA。
Qs_0283850—皂树(Q.saponaria)QA-Diα-1,3-L-鼠李糖基转移酶
Qs_0283870—皂树(Q.saponaria)QA-Diβ-1,3-D-木糖基转移酶
Qs-28-O-ApiT4—皂皮酸28-O-岩藻糖苷[1,2]-鼠李糖苷[1,4]木糖苷[1,3]芹菜糖基转移酶
Qs-28-O-FucT—皂皮酸28-O-岩藻糖基转移酶
Qs-28-O-RhaT—皂皮酸28-O-岩藻糖苷[1,2]-鼠李糖基转移酶
Qs-28-O-XylT3—皂皮酸28-O-岩藻糖苷[1,2]-鼠李糖苷[1,4]木糖基转移酶
Qs-28-O-XylT4—皂皮酸28-O-岩藻糖苷[1,2]-鼠李糖苷[1,4]木糖苷[1,3]木糖基转移酶
Qs-3-O-GalT—皂树(Q.saponaria)QA-Monoβ-1,2-D-半乳糖基转移酶
Qs-3-O-RhaT—皂树(Q.saponaria)QA-Diα-1,3-L-鼠李糖基转移酶
Qs-3-O-RhaT/XylT—皂树(Q.saponaria)QA-Di双β-1,3-D-木糖基转移酶/α-1,3-L-鼠李糖基转移酶
Qs-3-O-XylT—皂树(Q.saponaria)QA-Diβ-1,3-D-木糖基转移酶
QsAXS1—UDP-D-芹菜糖/UDP-D-木糖合酶
QsbAS—皂树(Q.saponaria)β-香树素合酶
QsCSL1—皂树(Q.saponaria)纤维素合酶-样酶(皂皮酸3-O-葡糖醛酸基转移酶)
QsCslG2—皂树(Q.saponaria)纤维素合酶-样酶(皂皮酸3-O-葡糖醛酸基转移酶)
QsCYP716-C-28—皂树(Q.saponaria)皂皮酸C-28氧化酶
QsCYP716-C-16α—皂树(Q.saponaria)皂皮酸C-16α氧化酶
QsCYP714-C-23—皂树(Q.saponaria)皂皮酸C-23氧化酶
QsFSL-1—加强岩藻糖基化皂苷生产的来自皂树(Q.saponaria)的酶
QsFSL-2—加强岩藻糖基化皂苷生产的来自皂树(Q.saponaria)的酶
QsFucSyn—加强岩藻糖基化皂苷生产的来自皂树(Q.saponaria)的酶
QsUGT_A6—与Qs-28-O-RhaT同义
QsUGT_A7—与Qs-28-O-XylT3同义
QsUGT_D2—与Qs-28-O-ApiT4同义
QsUGT_D3—与Qs-28-O-XylT4同义
QsUGT_L2—与Qs-28-O-FucT同义
Rhap—L-吡喃鼠李糖
RHM—鼠李糖合酶
SDR—短链脱氢酶/还原酶超家族
SOAP3—菠菜(Spinacia oleracea)苜蓿酸C-2β氧化酶。也称为CYP72A255。
SOAP4—菠菜(Spinacia oleracea)苜蓿酸C-23氧化酶。也称为CYP72A654。
SOAP5—菠菜(Spinacia oleracea)苜蓿酸3-O-葡糖醛酸基转移酶
SOAP6—菠菜(Spinacia oleracea)苜蓿酸-3-O-GlcA C-28D-岩藻糖基转移酶，也称为UGT74BB2SoFSL-1—加强岩藻糖基化皂苷生产的来自肥皂草(S.officinalis)的酶
SpolFSL—菠菜(Spinacia oleracea)FucSyn-样酶
tHMGR—糙伏毛燕麦(Avena strigosa)(二倍体燕麦)截短的3-羟基,3-甲基丁酰-CoA还原酶UDP-sugar—尿苷二磷酸糖
UGT—UDP-依赖性糖基转移酶
Xylp—D-吡喃木糖
参考文献
Arias MA et al.(2012)Glucopyranosyl Lipid Adjuvant(GLA),a SyntheticTLR4 Agonist,Promotes Potent Systemic and Mucosal Responses to IntranasalImmunization with HIVgp140.PLoS ONE 7(7):e41144.doi:10.1371/journal.pone.0041144.
Coler RN et al.(2011)Development and Characterization of SyntheticGlucopyranosyl Lipid Adjuvant System as a Vaccine Adjuvant.PLoS ONE 6(1):e16333.doi:10.1371/journal.pone.0016333
de Costa F,Barber CJS,Kim YB,Reed DW,Zhang H,Fett-Neto AG,CovelloPS.2017.Molecular cloning of an ester-forming triterpenoid:UDP-glucose 28-O-glucosyltransferase involved in saponin biosynthesis from the medicinal plantCentella asiatica.Plant Sci 262:9-17.
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Jozwiak,A.,Sonawane,P.,Panda,S.,Garagounis,C.,Papadopoulou,K.K.,Abebie,B.,Massalha,H.,Almekias-Siegl,E.,Scherg,T.,Aharoni,A.2020Plantterpenoid metabolism co-opts a component of the cell wall biosynthesismachinery.Nat Chem Biol,16(7):740-748.
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序列表
<110> 植物生物科学有限公司
<120> 方法和组合物
<130> P137731WO
<150> GB2020623.1
<151> 2020-12-24
<150> GB2116554.3
<151> 2021-11-17
<160> 54
<170> PatentIn version 3.5
<210> 1
<211> 1374
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 2的酶的核苷酸
<400> 1
atggagaatg ggagagttta caaatcccat gtcgtggtgc tcgcatttca cgggcaaggc 60
catattgttc cgttaatcca attatccaga cgattggcct ggaaaggcat caaaatcaca 120
tttgctacaa cacattcttg caccaaggcc attcaaacag gaagtgattc aatttcactt 180
ttatcaattt atgatgacat aactgatggt gggtttcaag gagaaggagg attcaagggc 240
ttccttcaga gatttgaagc cagtaccaca aggatcttac acgaattcgt caagaatcat 300
gaaaactcaa agaacccagt aaaatgctta atatatgatg ctaacttaat atgggctctg 360
gaaatggcaa agcaattggg tattgctact gctgcatttg tgtttccttc ttgggctgcc 420
attgccacct actatccctt ttatttagag gtgtatgcgg atcagcagat aaagaaggta 480
gatcctttca caatgcctga cttacctcca caacttggac ttccaaatat ggcatctctc 540
ggttcagatt cgggtcaaca ctcccccata ctcaaactca tgttgcaaca gttagaaaat 600
tttgggaaag ctgactggat cctgtctcac gcatttgaac agtttgaaca agaggtactt 660
gactggatga gaaatatcag cccagtaaca acaattggtc caactctgcc atctgtttat 720
cttgatggta ggctaaaaga tgacacagat tacggttaca atttgtacaa gccagatagt 780
gatacctgca tgaagtggct agacactaag gaaactgaat cagtggttta tatatcattt 840
ggcagtgttg cagatttgat cccagaacag atgacagaaa taacaaactc cctgaagaaa 900
atgagcagca actttctgtg ggtggtgaag gaaactgaaa aaaacaacct ccctagcagc 960
tttgttgagg agacaaaaga aaagggattg gtagtgactt ggtgccccca gttgaaggtg 1020
ttgtctcatc ctgcagtggg ttgtttcatt acacactgtg gaacaaattc catatttgag 1080
tcagtatgct ttgcagtgcc aatggtggga atgccacagt tttgtgatca aatgcctaat 1140
gcatatttca tggagaaggt ctggaaagta ggtgttaggc caagtttgga tgacaatggt 1200
gtcgtcactg gagaagaaat tgagcgatgt ataaaagtag ttaccgaagg agagagtggg 1260
caagagatta agaagaaact tgtgcagtgg aaagagcttg caaaagaggc agtggacgag 1320
ggtggaagtt cagataagca cattgatgaa ttcattgctg gaatcacaac ttga 1374
<210> 2
<211> 457
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 岩藻糖基转移酶，其能够将beta-d-岩藻吡喃糖苷转移至皂树皮酸的C-28位（Qs-28-O-FucT）
<400> 2
Met Glu Asn Gly Arg Val Tyr Lys Ser His Val Val Val Leu Ala Phe
1 5 10 15
His Gly Gln Gly His Ile Val Pro Leu Ile Gln Leu Ser Arg Arg Leu
20 25 30
Ala Trp Lys Gly Ile Lys Ile Thr Phe Ala Thr Thr His Ser Cys Thr
35 40 45
Lys Ala Ile Gln Thr Gly Ser Asp Ser Ile Ser Leu Leu Ser Ile Tyr
50 55 60
Asp Asp Ile Thr Asp Gly Gly Phe Gln Gly Glu Gly Gly Phe Lys Gly
65 70 75 80
Phe Leu Gln Arg Phe Glu Ala Ser Thr Thr Arg Ile Leu His Glu Phe
85 90 95
Val Lys Asn His Glu Asn Ser Lys Asn Pro Val Lys Cys Leu Ile Tyr
100 105 110
Asp Ala Asn Leu Ile Trp Ala Leu Glu Met Ala Lys Gln Leu Gly Ile
115 120 125
Ala Thr Ala Ala Phe Val Phe Pro Ser Trp Ala Ala Ile Ala Thr Tyr
130 135 140
Tyr Pro Phe Tyr Leu Glu Val Tyr Ala Asp Gln Gln Ile Lys Lys Val
145 150 155 160
Asp Pro Phe Thr Met Pro Asp Leu Pro Pro Gln Leu Gly Leu Pro Asn
165 170 175
Met Ala Ser Leu Gly Ser Asp Ser Gly Gln His Ser Pro Ile Leu Lys
180 185 190
Leu Met Leu Gln Gln Leu Glu Asn Phe Gly Lys Ala Asp Trp Ile Leu
195 200 205
Ser His Ala Phe Glu Gln Phe Glu Gln Glu Val Leu Asp Trp Met Arg
210 215 220
Asn Ile Ser Pro Val Thr Thr Ile Gly Pro Thr Leu Pro Ser Val Tyr
225 230 235 240
Leu Asp Gly Arg Leu Lys Asp Asp Thr Asp Tyr Gly Tyr Asn Leu Tyr
245 250 255
Lys Pro Asp Ser Asp Thr Cys Met Lys Trp Leu Asp Thr Lys Glu Thr
260 265 270
Glu Ser Val Val Tyr Ile Ser Phe Gly Ser Val Ala Asp Leu Ile Pro
275 280 285
Glu Gln Met Thr Glu Ile Thr Asn Ser Leu Lys Lys Met Ser Ser Asn
290 295 300
Phe Leu Trp Val Val Lys Glu Thr Glu Lys Asn Asn Leu Pro Ser Ser
305 310 315 320
Phe Val Glu Glu Thr Lys Glu Lys Gly Leu Val Val Thr Trp Cys Pro
325 330 335
Gln Leu Lys Val Leu Ser His Pro Ala Val Gly Cys Phe Ile Thr His
340 345 350
Cys Gly Thr Asn Ser Ile Phe Glu Ser Val Cys Phe Ala Val Pro Met
355 360 365
Val Gly Met Pro Gln Phe Cys Asp Gln Met Pro Asn Ala Tyr Phe Met
370 375 380
Glu Lys Val Trp Lys Val Gly Val Arg Pro Ser Leu Asp Asp Asn Gly
385 390 395 400
Val Val Thr Gly Glu Glu Ile Glu Arg Cys Ile Lys Val Val Thr Glu
405 410 415
Gly Glu Ser Gly Gln Glu Ile Lys Lys Lys Leu Val Gln Trp Lys Glu
420 425 430
Leu Ala Lys Glu Ala Val Asp Glu Gly Gly Ser Ser Asp Lys His Ile
435 440 445
Asp Glu Phe Ile Ala Gly Ile Thr Thr
450 455
<210> 3
<211> 1422
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 4的酶的核苷酸
<400> 3
atggcaaaaa ctgataagca gcttcacatc gccatgttcc catggctagc tatgggtcat 60
atattcccaa actttgagct cgctaagctc tttgctcaaa agggtcactc aattacttta 120
atctccaccc cacgaaacat cagtcgtctc cctcaaatcc ctacacattt agagcaattg 180
attaaattag tcagcttgcc tatattaccc aaacacaaag caaatctccc agagaatgca 240
gagtccacca tggacgttac ccccaataaa gtcccatacc ttaagatggc ctatgatggt 300
cttcaggagt cgttgactca attactgaaa tcttcagctc ccgattggat tctatatgac 360
tttgctgctg actggttacc accacttgtt cacagccttc aaatccgctg tgttttcttc 420
gtggtatccc ctgcgtggaa tctttgcttc tttgacactc ccaaaccaca gttgggcagt 480
gctgctgttt ttcgaacaaa gcctgaagac tatcttcgcc ctcccagttg ggttcctttc 540
cattcaaata ttgggctaaa gcttcacgag gtgaagaaaa tgtttgaagg ggtttcagat 600
aaagaaacag gggtcactgt aagttttaac ttcaacaaag cagtttcgag ctgtgacttg 660
ttttctttcc gcagctgcta tgaactcgaa tcagaatggc tgaacctggt ggaggatatt 720
tacaagaggc ctgtagttcc agtgggcgta attccaccct cttttcaagt cagaattgtg 780
aatgaagaag acaacaaacc agagtggtta aagatccaat cttggttaga taaacaagag 840
caaggatcgg tggtatacat agcatttggc agtgagctta agctgggcca acaagatctc 900
accgaattag ctcttggact tgagctttct gggttgccat tcttttgggc acttagaaag 960
cagcaagaca gctcatcagt agatttacca gatgggtttg aggaccgagt cagtgatcgt 1020
ggagttgttt gcagagactg ggtgccccaa cttaagatcc tagctcacgg gtcaattggg 1080
ggttatttga ctcactgtgg ttcaggttca gtgatagagg gacttcattt tgggcgtgtt 1140
cttgttatgc tgccctattt actagaccaa gcattatatg ctagagtatt ggaggagaaa 1200
aagctggggg ttgagatacc aaggaacgaa caagatgggt cttttactag gagctcagtg 1260
gccaagtctg tgaagttggc catagtggat gaggggggaa gtatttacag ggacaaagcc 1320
aaagagatgg gcttggtatt cagtgacaaa gatcgtcatg aacaatacat tgagaatttc 1380
cttcaacacc ttcaacacaa aagggaacct ttccaaattt aa 1422
<210> 4
<211> 473
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 鼠李糖基转移酶，其能够将alpha-1,2-l-吡喃鼠李糖转移至QA-F（Qs-28-O-RhaT）
<400> 4
Met Ala Lys Thr Asp Lys Gln Leu His Ile Ala Met Phe Pro Trp Leu
1 5 10 15
Ala Met Gly His Ile Phe Pro Asn Phe Glu Leu Ala Lys Leu Phe Ala
20 25 30
Gln Lys Gly His Ser Ile Thr Leu Ile Ser Thr Pro Arg Asn Ile Ser
35 40 45
Arg Leu Pro Gln Ile Pro Thr His Leu Glu Gln Leu Ile Lys Leu Val
50 55 60
Ser Leu Pro Ile Leu Pro Lys His Lys Ala Asn Leu Pro Glu Asn Ala
65 70 75 80
Glu Ser Thr Met Asp Val Thr Pro Asn Lys Val Pro Tyr Leu Lys Met
85 90 95
Ala Tyr Asp Gly Leu Gln Glu Ser Leu Thr Gln Leu Leu Lys Ser Ser
100 105 110
Ala Pro Asp Trp Ile Leu Tyr Asp Phe Ala Ala Asp Trp Leu Pro Pro
115 120 125
Leu Val His Ser Leu Gln Ile Arg Cys Val Phe Phe Val Val Ser Pro
130 135 140
Ala Trp Asn Leu Cys Phe Phe Asp Thr Pro Lys Pro Gln Leu Gly Ser
145 150 155 160
Ala Ala Val Phe Arg Thr Lys Pro Glu Asp Tyr Leu Arg Pro Pro Ser
165 170 175
Trp Val Pro Phe His Ser Asn Ile Gly Leu Lys Leu His Glu Val Lys
180 185 190
Lys Met Phe Glu Gly Val Ser Asp Lys Glu Thr Gly Val Thr Val Ser
195 200 205
Phe Asn Phe Asn Lys Ala Val Ser Ser Cys Asp Leu Phe Ser Phe Arg
210 215 220
Ser Cys Tyr Glu Leu Glu Ser Glu Trp Leu Asn Leu Val Glu Asp Ile
225 230 235 240
Tyr Lys Arg Pro Val Val Pro Val Gly Val Ile Pro Pro Ser Phe Gln
245 250 255
Val Arg Ile Val Asn Glu Glu Asp Asn Lys Pro Glu Trp Leu Lys Ile
260 265 270
Gln Ser Trp Leu Asp Lys Gln Glu Gln Gly Ser Val Val Tyr Ile Ala
275 280 285
Phe Gly Ser Glu Leu Lys Leu Gly Gln Gln Asp Leu Thr Glu Leu Ala
290 295 300
Leu Gly Leu Glu Leu Ser Gly Leu Pro Phe Phe Trp Ala Leu Arg Lys
305 310 315 320
Gln Gln Asp Ser Ser Ser Val Asp Leu Pro Asp Gly Phe Glu Asp Arg
325 330 335
Val Ser Asp Arg Gly Val Val Cys Arg Asp Trp Val Pro Gln Leu Lys
340 345 350
Ile Leu Ala His Gly Ser Ile Gly Gly Tyr Leu Thr His Cys Gly Ser
355 360 365
Gly Ser Val Ile Glu Gly Leu His Phe Gly Arg Val Leu Val Met Leu
370 375 380
Pro Tyr Leu Leu Asp Gln Ala Leu Tyr Ala Arg Val Leu Glu Glu Lys
385 390 395 400
Lys Leu Gly Val Glu Ile Pro Arg Asn Glu Gln Asp Gly Ser Phe Thr
405 410 415
Arg Ser Ser Val Ala Lys Ser Val Lys Leu Ala Ile Val Asp Glu Gly
420 425 430
Gly Ser Ile Tyr Arg Asp Lys Ala Lys Glu Met Gly Leu Val Phe Ser
435 440 445
Asp Lys Asp Arg His Glu Gln Tyr Ile Glu Asn Phe Leu Gln His Leu
450 455 460
Gln His Lys Arg Glu Pro Phe Gln Ile
465 470
<210> 5
<211> 1395
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 6的酶的核苷酸
<400> 5
atggctgctg cagctcccaa tcacaggctc cacatagcat tcttcccatg gttagcattt 60
ggtcacataa accctttctt tgagcttgcg aagctcattg ctcaaaaggg tcatcatatt 120
tctttcattt ccaccccaag aaacatccaa cgcctttcac aagttcctcc acaattagca 180
gattccatag atctagtgag cttaccagta atccataatt caaacctccc agaaaacgca 240
gagtccacca tggacattcc acctgataaa accccttacc ttgggatgct tcacgacagt 300
ctcaaagaac cccttactca attccttcaa actcattccc ctgattggat tctgtatgac 360
ttttcagctg gttggcttgc tgccatagta gaagaccttg gtatctccca cggctacttt 420
tctatcattc cctgttggaa cataggcttc aatggacgcc aaatgaatgg tttccaaaag 480
ccagatattt cattgccctc cgccgtgtcg cttaagaaat atgaggtgaa gaaaatcatg 540
gatttggtca aatcttttcc caaaattttg gatgagtcgg ccactaaatc catagcttcg 600
cattcgacct gtgaagtaat ttttatacga aattgccccg agattgaagc agattggttc 660
gactatactt cgaaaatttt cgataaacca gtggttccgg tgggcgtagt gcccccatct 720
gtgcacataa ctaacaaaga gaaggacgag catttcaaca aatggttgga gatcaaagaa 780
tggttggatc aacaagacag aggttctgta atttatatag cttttggaac tgaatcactg 840
ccaaatcagg atgaaatcac catgcttgct caagggcttg agctatgtgg gcttcctttc 900
ttttgggcat taaggaagtc taatgtggct tctgatcagc caaattcaga ctcagttgag 960
ctaccggagg gatttgaaga acaaaccaaa ggtcgtggaa ttgtgtggac gagttgggca 1020
cctcaacaga gaattctggg tcacaattca attgggggtt ttgtgactca ctgtggttgg 1080
agttcagtaa tagaaggaat tcactatgga cggccactga ttatgttccc tctaacagtc 1140
gaacagtctc tgaatgctag gattttgggg gagaagaagt tgggtatgga agtacccaga 1200
gaagatgatg ggtcttttac aggtgaagtt gtggcagaga cattgaagct ggtattgctg 1260
gaccaagatg ggaaagttta cagggacaag gtaacagaga tgagtaaggt atttggggac 1320
aaagacaaac atgagaaata catgggtgat ctacttgaat tcttcaaaaa ttacaggtct 1380
cttaagagga attag 1395
<210> 6
<211> 464
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 木糖基转移酶，其能够将beta-1,4-d-吡喃木糖转移至QA-FR（Qs-28-O-XylT3）
<400> 6
Met Ala Ala Ala Ala Pro Asn His Arg Leu His Ile Ala Phe Phe Pro
1 5 10 15
Trp Leu Ala Phe Gly His Ile Asn Pro Phe Phe Glu Leu Ala Lys Leu
20 25 30
Ile Ala Gln Lys Gly His His Ile Ser Phe Ile Ser Thr Pro Arg Asn
35 40 45
Ile Gln Arg Leu Ser Gln Val Pro Pro Gln Leu Ala Asp Ser Ile Asp
50 55 60
Leu Val Ser Leu Pro Val Ile His Asn Ser Asn Leu Pro Glu Asn Ala
65 70 75 80
Glu Ser Thr Met Asp Ile Pro Pro Asp Lys Thr Pro Tyr Leu Gly Met
85 90 95
Leu His Asp Ser Leu Lys Glu Pro Leu Thr Gln Phe Leu Gln Thr His
100 105 110
Ser Pro Asp Trp Ile Leu Tyr Asp Phe Ser Ala Gly Trp Leu Ala Ala
115 120 125
Ile Val Glu Asp Leu Gly Ile Ser His Gly Tyr Phe Ser Ile Ile Pro
130 135 140
Cys Trp Asn Ile Gly Phe Asn Gly Arg Gln Met Asn Gly Phe Gln Lys
145 150 155 160
Pro Asp Ile Ser Leu Pro Ser Ala Val Ser Leu Lys Lys Tyr Glu Val
165 170 175
Lys Lys Ile Met Asp Leu Val Lys Ser Phe Pro Lys Ile Leu Asp Glu
180 185 190
Ser Ala Thr Lys Ser Ile Ala Ser His Ser Thr Cys Glu Val Ile Phe
195 200 205
Ile Arg Asn Cys Pro Glu Ile Glu Ala Asp Trp Phe Asp Tyr Thr Ser
210 215 220
Lys Ile Phe Asp Lys Pro Val Val Pro Val Gly Val Val Pro Pro Ser
225 230 235 240
Val His Ile Thr Asn Lys Glu Lys Asp Glu His Phe Asn Lys Trp Leu
245 250 255
Glu Ile Lys Glu Trp Leu Asp Gln Gln Asp Arg Gly Ser Val Ile Tyr
260 265 270
Ile Ala Phe Gly Thr Glu Ser Leu Pro Asn Gln Asp Glu Ile Thr Met
275 280 285
Leu Ala Gln Gly Leu Glu Leu Cys Gly Leu Pro Phe Phe Trp Ala Leu
290 295 300
Arg Lys Ser Asn Val Ala Ser Asp Gln Pro Asn Ser Asp Ser Val Glu
305 310 315 320
Leu Pro Glu Gly Phe Glu Glu Gln Thr Lys Gly Arg Gly Ile Val Trp
325 330 335
Thr Ser Trp Ala Pro Gln Gln Arg Ile Leu Gly His Asn Ser Ile Gly
340 345 350
Gly Phe Val Thr His Cys Gly Trp Ser Ser Val Ile Glu Gly Ile His
355 360 365
Tyr Gly Arg Pro Leu Ile Met Phe Pro Leu Thr Val Glu Gln Ser Leu
370 375 380
Asn Ala Arg Ile Leu Gly Glu Lys Lys Leu Gly Met Glu Val Pro Arg
385 390 395 400
Glu Asp Asp Gly Ser Phe Thr Gly Glu Val Val Ala Glu Thr Leu Lys
405 410 415
Leu Val Leu Leu Asp Gln Asp Gly Lys Val Tyr Arg Asp Lys Val Thr
420 425 430
Glu Met Ser Lys Val Phe Gly Asp Lys Asp Lys His Glu Lys Tyr Met
435 440 445
Gly Asp Leu Leu Glu Phe Phe Lys Asn Tyr Arg Ser Leu Lys Arg Asn
450 455 460
<210> 7
<211> 1530
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 8的酶的核苷酸
<400> 7
atggactcca cccacttgca gccggccact actcctctga aaattcactt catacctttc 60
atatctccgg gtcacatcat cccactctct gaattggctc gtatctttgc ttcacgcggt 120
gagcatgtga ctatcattac cactcctttc aacgctgacc tacttcagaa atccattgac 180
gaagacagag attccggcga gcacattggc atccacaccg ttgaatggtc agccacagag 240
ctaggccttc ctcatgggat tgaaaatctc agcaacgtca ctgacttgga gaccgccatt 300
aagctacaca gggccctcat gctaatgcag aaacagatgg aagatttcat gacccgaaat 360
ccacccgatt gtataattgc cgacacgttt tacccgtggg cctccgaatt tgctaatcgg 420
atgggtatcc cgagactcat tttctacccg tggagtactt tcgcgctctg tttgatggaa 480
tctattcgat ctcccgactc cccgcaccga agattgagtt cggattcgga tccatttgtg 540
gttccgggtc ttcctcaccc gatcatcttg acccgttctc agcttccgga acacgatcga 600
aaggacatag cggacccggc tgcccaactc atggatcagc ataaagaaac tgagatgaag 660
agctacggaa ttattctcaa caatttcgcg gagatcgaaa cagaatacac agagcattac 720
aagaaaataa cgggtcacaa ggtttggcac attggacctg ccgcagcaat tgttcaccga 780
aatgccaaag agaaggcaga gagggtattc aagagtgatg agcatgacaa taaccttgtc 840
atcaattggc tcaactcgaa ggaaccaaac tcagttgttt atgtttgttt cggcagcgga 900
tgtcaattcc ctgataaaca actctatgag attgcatgcg ggttagagtt atctgggcat 960
caatttgttt gggtggttcg cggaaaagat aaacaaatcg atgttaatga cgatggggag 1020
aagacatggt tgcctaaagg gtttgaggaa agaatgaaaa cagaaaataa aggtttgatt 1080
gtaaggggat gggccccaca ggtgctggtt ttggatcatc catcattggg atgtttcttg 1140
acgcattgcg gctggaattc tacgattgag ggaatcacag caggcgttcc tttgatcacg 1200
tggccagtat tcgccgagca attctataat gagaagctaa tcacgcaggt gcatgggaat 1260
ggggtggtgg ttggttcaga ggagtggatc atgttgttca ccgtcgctaa aagcttggta 1320
agtagagaca aaattgagaa tgctgtgagg aagataatgg acggtggtga tgaggctgta 1380
caaatcagaa ggcgggcccg ggaacttgga gaaaaagctt ggaaagctgc ttcaactggg 1440
gggtcctcct acaataatct aaccgcagca attgaagacc ttaagcggtt gagagaggac 1500
cgttcgaagc tgaaaacaaa aacaatttga 1530
<210> 8
<211> 509
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 木糖基转移酶，其能够将beta-1,3-d-吡喃木糖转移至QA-FRX（Qs-28-O-XylT4）
<400> 8
Met Asp Ser Thr His Leu Gln Pro Ala Thr Thr Pro Leu Lys Ile His
1 5 10 15
Phe Ile Pro Phe Ile Ser Pro Gly His Ile Ile Pro Leu Ser Glu Leu
20 25 30
Ala Arg Ile Phe Ala Ser Arg Gly Glu His Val Thr Ile Ile Thr Thr
35 40 45
Pro Phe Asn Ala Asp Leu Leu Gln Lys Ser Ile Asp Glu Asp Arg Asp
50 55 60
Ser Gly Glu His Ile Gly Ile His Thr Val Glu Trp Ser Ala Thr Glu
65 70 75 80
Leu Gly Leu Pro His Gly Ile Glu Asn Leu Ser Asn Val Thr Asp Leu
85 90 95
Glu Thr Ala Ile Lys Leu His Arg Ala Leu Met Leu Met Gln Lys Gln
100 105 110
Met Glu Asp Phe Met Thr Arg Asn Pro Pro Asp Cys Ile Ile Ala Asp
115 120 125
Thr Phe Tyr Pro Trp Ala Ser Glu Phe Ala Asn Arg Met Gly Ile Pro
130 135 140
Arg Leu Ile Phe Tyr Pro Trp Ser Thr Phe Ala Leu Cys Leu Met Glu
145 150 155 160
Ser Ile Arg Ser Pro Asp Ser Pro His Arg Arg Leu Ser Ser Asp Ser
165 170 175
Asp Pro Phe Val Val Pro Gly Leu Pro His Pro Ile Ile Leu Thr Arg
180 185 190
Ser Gln Leu Pro Glu His Asp Arg Lys Asp Ile Ala Asp Pro Ala Ala
195 200 205
Gln Leu Met Asp Gln His Lys Glu Thr Glu Met Lys Ser Tyr Gly Ile
210 215 220
Ile Leu Asn Asn Phe Ala Glu Ile Glu Thr Glu Tyr Thr Glu His Tyr
225 230 235 240
Lys Lys Ile Thr Gly His Lys Val Trp His Ile Gly Pro Ala Ala Ala
245 250 255
Ile Val His Arg Asn Ala Lys Glu Lys Ala Glu Arg Val Phe Lys Ser
260 265 270
Asp Glu His Asp Asn Asn Leu Val Ile Asn Trp Leu Asn Ser Lys Glu
275 280 285
Pro Asn Ser Val Val Tyr Val Cys Phe Gly Ser Gly Cys Gln Phe Pro
290 295 300
Asp Lys Gln Leu Tyr Glu Ile Ala Cys Gly Leu Glu Leu Ser Gly His
305 310 315 320
Gln Phe Val Trp Val Val Arg Gly Lys Asp Lys Gln Ile Asp Val Asn
325 330 335
Asp Asp Gly Glu Lys Thr Trp Leu Pro Lys Gly Phe Glu Glu Arg Met
340 345 350
Lys Thr Glu Asn Lys Gly Leu Ile Val Arg Gly Trp Ala Pro Gln Val
355 360 365
Leu Val Leu Asp His Pro Ser Leu Gly Cys Phe Leu Thr His Cys Gly
370 375 380
Trp Asn Ser Thr Ile Glu Gly Ile Thr Ala Gly Val Pro Leu Ile Thr
385 390 395 400
Trp Pro Val Phe Ala Glu Gln Phe Tyr Asn Glu Lys Leu Ile Thr Gln
405 410 415
Val His Gly Asn Gly Val Val Val Gly Ser Glu Glu Trp Ile Met Leu
420 425 430
Phe Thr Val Ala Lys Ser Leu Val Ser Arg Asp Lys Ile Glu Asn Ala
435 440 445
Val Arg Lys Ile Met Asp Gly Gly Asp Glu Ala Val Gln Ile Arg Arg
450 455 460
Arg Ala Arg Glu Leu Gly Glu Lys Ala Trp Lys Ala Ala Ser Thr Gly
465 470 475 480
Gly Ser Ser Tyr Asn Asn Leu Thr Ala Ala Ile Glu Asp Leu Lys Arg
485 490 495
Leu Arg Glu Asp Arg Ser Lys Leu Lys Thr Lys Thr Ile
500 505
<210> 9
<211> 1530
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 10的酶的核苷酸
<400> 9
atggactcca cccacttgca gccggccact actcctctga aaattcacgt catacctttc 60
atagctccgg gtcacattat cccactctct gaattggctc gtatctttgc ttcacgcggt 120
gagcatgtga ctatcataac cactcctttc aacgctgacc tacttcagaa atccattgac 180
gaagacagag attccggcga gcacattggc atccacaccg ttgaatggtc agccacagag 240
ctaggccttc ctcatggggt tgaaaatctc agcaacgtca ctgacttgga gaccggcatt 300
aagctacaca gggccctcgt gctaatgcag aaacagatgg aagatttcat gacccgaaat 360
ccacccgatt gtataattgc cgacacgttt tacccgtggg cctccgaatt tgctaatcgg 420
atgggtatcc cgagactcat tttcttcccg gggtgtactt tcgcgctctg tttgatggaa 480
tctattcgat ctcccgactc cccgcaccga agattgagtt cggattcgga cccatttgtg 540
gttccgggtc ttcctcaccc gatcatcttg acccgttctc aacttccgga acacgatcga 600
gaggacatag cggacccggc tgcccaattc atggatcagt gtaaagaagc tgcgatgaag 660
agctacggaa ttattctcaa caatttcgcg gagatcgaaa cagaatacac agagcattac 720
aagaaaataa cgggtcacaa ggtttggcac attggacctg ccgcagcaat tgttcaccga 780
aatgccaaag agaaggcaga ggggcttttc aaaagtgacg agcatgacaa taaccttgtc 840
atcaattggc tcaactcgaa ggaaccaaac tcagttgttt atgtttgttt cggcagcgga 900
tgtcaattcc ctgataaaca actctatgag attgcatgcg ggttagagtt atctgggcat 960
caatttattt gggtggttcg cggcaaagat aaacaaatcg atgttaatga cgatgaggag 1020
aagacatggt tgcctaaagg gtttgaggaa agaatgaaaa cagaaaataa aggtttgatt 1080
gtaaggggat gggccccaca ggtgctggtt ttggatcatc catcgttggg atgtttcttg 1140
acgcattgcg gctggaattc tacgattgag ggaatcacag caggtgttcc tttgatcacg 1200
tggccagtat actccgagca attctataat gagaagctaa tcacgcaggt gcatggtaat 1260
ggggtggggg ttggttcaga ggagtggatc atgctgttca gcgtcgctaa aagtttggta 1320
agtagagaca aaattgagaa tgctgtgagg aagataatgg acggtggtga tgaggcttta 1380
gaaatcagaa ggcgggcccg ggaacttgga gaaaaagcta ggaaagctgc ttcaattggg 1440
gggtcctccg acaataatct aaccgcagca attgaagacc ttaagcggtt gagagaggac 1500
cgttcgaagc tgaaaacaaa aacaatttga 1530
<210> 10
<211> 509
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 芹菜糖基转移酶，其能够将beta-1,3-d-呋喃芹菜糖转移至QA-FRX（Qs-28-O-ApiT4）
<400> 10
Met Asp Ser Thr His Leu Gln Pro Ala Thr Thr Pro Leu Lys Ile His
1 5 10 15
Val Ile Pro Phe Ile Ala Pro Gly His Ile Ile Pro Leu Ser Glu Leu
20 25 30
Ala Arg Ile Phe Ala Ser Arg Gly Glu His Val Thr Ile Ile Thr Thr
35 40 45
Pro Phe Asn Ala Asp Leu Leu Gln Lys Ser Ile Asp Glu Asp Arg Asp
50 55 60
Ser Gly Glu His Ile Gly Ile His Thr Val Glu Trp Ser Ala Thr Glu
65 70 75 80
Leu Gly Leu Pro His Gly Val Glu Asn Leu Ser Asn Val Thr Asp Leu
85 90 95
Glu Thr Gly Ile Lys Leu His Arg Ala Leu Val Leu Met Gln Lys Gln
100 105 110
Met Glu Asp Phe Met Thr Arg Asn Pro Pro Asp Cys Ile Ile Ala Asp
115 120 125
Thr Phe Tyr Pro Trp Ala Ser Glu Phe Ala Asn Arg Met Gly Ile Pro
130 135 140
Arg Leu Ile Phe Phe Pro Gly Cys Thr Phe Ala Leu Cys Leu Met Glu
145 150 155 160
Ser Ile Arg Ser Pro Asp Ser Pro His Arg Arg Leu Ser Ser Asp Ser
165 170 175
Asp Pro Phe Val Val Pro Gly Leu Pro His Pro Ile Ile Leu Thr Arg
180 185 190
Ser Gln Leu Pro Glu His Asp Arg Glu Asp Ile Ala Asp Pro Ala Ala
195 200 205
Gln Phe Met Asp Gln Cys Lys Glu Ala Ala Met Lys Ser Tyr Gly Ile
210 215 220
Ile Leu Asn Asn Phe Ala Glu Ile Glu Thr Glu Tyr Thr Glu His Tyr
225 230 235 240
Lys Lys Ile Thr Gly His Lys Val Trp His Ile Gly Pro Ala Ala Ala
245 250 255
Ile Val His Arg Asn Ala Lys Glu Lys Ala Glu Gly Leu Phe Lys Ser
260 265 270
Asp Glu His Asp Asn Asn Leu Val Ile Asn Trp Leu Asn Ser Lys Glu
275 280 285
Pro Asn Ser Val Val Tyr Val Cys Phe Gly Ser Gly Cys Gln Phe Pro
290 295 300
Asp Lys Gln Leu Tyr Glu Ile Ala Cys Gly Leu Glu Leu Ser Gly His
305 310 315 320
Gln Phe Ile Trp Val Val Arg Gly Lys Asp Lys Gln Ile Asp Val Asn
325 330 335
Asp Asp Glu Glu Lys Thr Trp Leu Pro Lys Gly Phe Glu Glu Arg Met
340 345 350
Lys Thr Glu Asn Lys Gly Leu Ile Val Arg Gly Trp Ala Pro Gln Val
355 360 365
Leu Val Leu Asp His Pro Ser Leu Gly Cys Phe Leu Thr His Cys Gly
370 375 380
Trp Asn Ser Thr Ile Glu Gly Ile Thr Ala Gly Val Pro Leu Ile Thr
385 390 395 400
Trp Pro Val Tyr Ser Glu Gln Phe Tyr Asn Glu Lys Leu Ile Thr Gln
405 410 415
Val His Gly Asn Gly Val Gly Val Gly Ser Glu Glu Trp Ile Met Leu
420 425 430
Phe Ser Val Ala Lys Ser Leu Val Ser Arg Asp Lys Ile Glu Asn Ala
435 440 445
Val Arg Lys Ile Met Asp Gly Gly Asp Glu Ala Leu Glu Ile Arg Arg
450 455 460
Arg Ala Arg Glu Leu Gly Glu Lys Ala Arg Lys Ala Ala Ser Ile Gly
465 470 475 480
Gly Ser Ser Asp Asn Asn Leu Thr Ala Ala Ile Glu Asp Leu Lys Arg
485 490 495
Leu Arg Glu Asp Arg Ser Lys Leu Lys Thr Lys Thr Ile
500 505
<210> 11
<211> 897
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 12的酶的核苷酸
<400> 11
atggcagaag caacgcagag gtatgctgtt gtgacaggat ctaataaggg aattggattt 60
gggatatgca agcagttggc ttctaaggga atcaaagtag tgttaacagc tagagatgag 120
aagagaggtc ttgaagcagt tgagaaattg aaagaaatta gtctggctgg tcatgtggtt 180
tttcatcaac tcgatgtgtc tgatcctgct agtgttacta gccttgaaga tttcatcaaa 240
acccagtttg ggaagctaga tattctggta aacaatgctg ggataacagg aacaactgta 300
gatgctgatg ctttagcagc ttcaggcttc ggtacagggg gtgaacgtaa gcctattgat 360
tggagtaagt tagtgataca gacttatgaa tcagttgaaa aagctttcaa cacaaactat 420
tacggtggca aaagaatgac agaagcactt atacccctcc tccagctatc agactcaccc 480
aggattgtta atgtttcctc tgctatggga cagttagaga atatacctag tggatgggca 540
aaggaagtgc tcacagatgt tgataaccta acagaaggaa aattggatga ggtttcaacc 600
cagtttttga aagatttcaa agagggttca ttggaaacca aaggctggcc tagtcttatg 660
tcttcttata tagtctcaaa agctgtttta aatgcctaca caaggattct tgctaagaaa 720
tacccagctt tctgcatcaa ttgtgtagat cctggctatg tgaagacaga cataaaccat 780
catactggcc aattaagtgt tgatgaaggt gctgaaagtc ctgtaagact ggccttgctg 840
cctaatggtg gtccttctgg cgtgttcttc tccaggacag aagaagcacc attttga 897
<210> 12
<211> 298
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 氧化还原酶，其能够增强岩藻糖基转移酶的活性（QsFucSyn）
<400> 12
Met Ala Glu Ala Thr Gln Arg Tyr Ala Val Val Thr Gly Ser Asn Lys
1 5 10 15
Gly Ile Gly Phe Gly Ile Cys Lys Gln Leu Ala Ser Lys Gly Ile Lys
20 25 30
Val Val Leu Thr Ala Arg Asp Glu Lys Arg Gly Leu Glu Ala Val Glu
35 40 45
Lys Leu Lys Glu Ile Ser Leu Ala Gly His Val Val Phe His Gln Leu
50 55 60
Asp Val Ser Asp Pro Ala Ser Val Thr Ser Leu Glu Asp Phe Ile Lys
65 70 75 80
Thr Gln Phe Gly Lys Leu Asp Ile Leu Val Asn Asn Ala Gly Ile Thr
85 90 95
Gly Thr Thr Val Asp Ala Asp Ala Leu Ala Ala Ser Gly Phe Gly Thr
100 105 110
Gly Gly Glu Arg Lys Pro Ile Asp Trp Ser Lys Leu Val Ile Gln Thr
115 120 125
Tyr Glu Ser Val Glu Lys Ala Phe Asn Thr Asn Tyr Tyr Gly Gly Lys
130 135 140
Arg Met Thr Glu Ala Leu Ile Pro Leu Leu Gln Leu Ser Asp Ser Pro
145 150 155 160
Arg Ile Val Asn Val Ser Ser Ala Met Gly Gln Leu Glu Asn Ile Pro
165 170 175
Ser Gly Trp Ala Lys Glu Val Leu Thr Asp Val Asp Asn Leu Thr Glu
180 185 190
Gly Lys Leu Asp Glu Val Ser Thr Gln Phe Leu Lys Asp Phe Lys Glu
195 200 205
Gly Ser Leu Glu Thr Lys Gly Trp Pro Ser Leu Met Ser Ser Tyr Ile
210 215 220
Val Ser Lys Ala Val Leu Asn Ala Tyr Thr Arg Ile Leu Ala Lys Lys
225 230 235 240
Tyr Pro Ala Phe Cys Ile Asn Cys Val Asp Pro Gly Tyr Val Lys Thr
245 250 255
Asp Ile Asn His His Thr Gly Gln Leu Ser Val Asp Glu Gly Ala Glu
260 265 270
Ser Pro Val Arg Leu Ala Leu Leu Pro Asn Gly Gly Pro Ser Gly Val
275 280 285
Phe Phe Ser Arg Thr Glu Glu Ala Pro Phe
290 295
<210> 13
<211> 1197
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 14的酶的核苷酸
<400> 13
atgccaactt tgtacaaaaa agcaggctta atggcgtcgg cgtcaagggt agatctggat 60
ggtaatcaga taaagccgat gacaatttgc atgatcggtg ccggtgggtt cattgggtcc 120
cacctctgcg agaagattat ggcggagaca ccgcacaagg ttctggcatt agatgtctac 180
aatgacaaga tcaagcactt actggagccg gattctcttc aatggaaaga tcgcatccaa 240
ttccaccgca tcaacattaa gcacgattcg aggctcgaag gtctcatcaa gatggcagat 300
ctgactataa atctggctgc tatttgtact cccgcggatt acaacacccg tcctctggac 360
acaatttata gcaatttcat tgacgctctt cctgtggtaa agtactgttc ggagaataac 420
aagcgtctca ttcatttctc tacgtgtgaa gtgtatggga aaacgattgg gagctttctc 480
ccaaaagaca gccctcttct aaaggatcct gaatattttg ttcttaaaga agatgcctcc 540
ccatgcatat ttggtcctat tgaaaagcag agatggtcct acgcatgtgc aaagcaattg 600
attgagaggc tggtttatgc tgagggtgct gagaatggcc ttgagttcac tattgtgcga 660
cctttcaatt ggattggccc cagaatggat ttcatacctg gcattgatgg tccaagtgaa 720
ggtgttccac gggttctggc atgctttagt aacaatctcc ttcgcggtga gccactcaaa 780
ctcgttgatg gtggccaatc ccagagaact tttgtttata tcaaggatgc aattgaagct 840
gttttgttga tgattgaaaa ccctgccagg gctaatggtc atatttttaa tgtgggtaac 900
cctcacaatg aagttacagt tcggcaactt gctgaaatga tgaccgaggt ctattctaag 960
gtaagtggag aaccgtctct tgaggtgcct accattgatg taagctccaa agaattttat 1020
ggtgaaggat acgatgatag tgacaagaga attcctgaca tgaccataat caacaggcaa 1080
cttggctgga accctaagac atcgctctgg gatcttcttg agtcgaccct cacctatcaa 1140
cataggacat atgcagaagc tattaagaaa tcaattgcga aaccagttgc cagctag 1197
<210> 14
<211> 398
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 能够增强芹菜糖基转移酶的活性的酶（QsAXS1）
<400> 14
Met Pro Thr Leu Tyr Lys Lys Ala Gly Leu Met Ala Ser Ala Ser Arg
1 5 10 15
Val Asp Leu Asp Gly Asn Gln Ile Lys Pro Met Thr Ile Cys Met Ile
20 25 30
Gly Ala Gly Gly Phe Ile Gly Ser His Leu Cys Glu Lys Ile Met Ala
35 40 45
Glu Thr Pro His Lys Val Leu Ala Leu Asp Val Tyr Asn Asp Lys Ile
50 55 60
Lys His Leu Leu Glu Pro Asp Ser Leu Gln Trp Lys Asp Arg Ile Gln
65 70 75 80
Phe His Arg Ile Asn Ile Lys His Asp Ser Arg Leu Glu Gly Leu Ile
85 90 95
Lys Met Ala Asp Leu Thr Ile Asn Leu Ala Ala Ile Cys Thr Pro Ala
100 105 110
Asp Tyr Asn Thr Arg Pro Leu Asp Thr Ile Tyr Ser Asn Phe Ile Asp
115 120 125
Ala Leu Pro Val Val Lys Tyr Cys Ser Glu Asn Asn Lys Arg Leu Ile
130 135 140
His Phe Ser Thr Cys Glu Val Tyr Gly Lys Thr Ile Gly Ser Phe Leu
145 150 155 160
Pro Lys Asp Ser Pro Leu Leu Lys Asp Pro Glu Tyr Phe Val Leu Lys
165 170 175
Glu Asp Ala Ser Pro Cys Ile Phe Gly Pro Ile Glu Lys Gln Arg Trp
180 185 190
Ser Tyr Ala Cys Ala Lys Gln Leu Ile Glu Arg Leu Val Tyr Ala Glu
195 200 205
Gly Ala Glu Asn Gly Leu Glu Phe Thr Ile Val Arg Pro Phe Asn Trp
210 215 220
Ile Gly Pro Arg Met Asp Phe Ile Pro Gly Ile Asp Gly Pro Ser Glu
225 230 235 240
Gly Val Pro Arg Val Leu Ala Cys Phe Ser Asn Asn Leu Leu Arg Gly
245 250 255
Glu Pro Leu Lys Leu Val Asp Gly Gly Gln Ser Gln Arg Thr Phe Val
260 265 270
Tyr Ile Lys Asp Ala Ile Glu Ala Val Leu Leu Met Ile Glu Asn Pro
275 280 285
Ala Arg Ala Asn Gly His Ile Phe Asn Val Gly Asn Pro His Asn Glu
290 295 300
Val Thr Val Arg Gln Leu Ala Glu Met Met Thr Glu Val Tyr Ser Lys
305 310 315 320
Val Ser Gly Glu Pro Ser Leu Glu Val Pro Thr Ile Asp Val Ser Ser
325 330 335
Lys Glu Phe Tyr Gly Glu Gly Tyr Asp Asp Ser Asp Lys Arg Ile Pro
340 345 350
Asp Met Thr Ile Ile Asn Arg Gln Leu Gly Trp Asn Pro Lys Thr Ser
355 360 365
Leu Trp Asp Leu Leu Glu Ser Thr Leu Thr Tyr Gln His Arg Thr Tyr
370 375 380
Ala Glu Ala Ile Lys Lys Ser Ile Ala Lys Pro Val Ala Ser
385 390 395
<210> 15
<211> 1275
<212> DNA
<213> 糙伏毛燕麦（Avena strigosa）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 16的酶的核苷酸
<400> 15
atggcgcccg agaaaatgcc cgaggaggac gaggaaatcg tcgccggggt cgtcgcaggg 60
aagatcccct cctacgtgct cgagaccagg ctaggcgact gccgcagggc agccgggatc 120
cgccgcgagg cgctgcgccg gatcaccggc agggagatcg acggccttcc cctcgacggc 180
ttcgactacg actcgattct cggacagtgc tgcgagatgc ccgtcgggta cgtgcagctg 240
ccggtcggcg tcgcggggcc gctcgtcctc gacggccgcc gcatatacgt cccgatggcc 300
accacggagg gctgcctaat cgccagcacc aaccgcggat gcaaggccat tgccgagtcc 360
ggaggcgcat ccagcgtcgt gtaccgcgac gggatgaccc gcgcccccgt agcccgcttc 420
ccctccgcac gacgcgccgc agagctcaag ggcttcctgg agaatccggc caactacgac 480
accctgtccg tggtctttaa cagatcaagc agatttgcaa ggctgcaggg ggtcaagtgc 540
gccatggctg ggaggaactt gtacatgagg ttcacctgca gcaccgggga tgccatgggg 600
atgaacatgg tctccaaggg cgtccaaaat gtgctcgact atctgcagga ggacttccct 660
gacatggacg ttgtcagcat ctcaggcaac ttttgttccg acaagaaatc agctgctgta 720
aactggattg aaggccgtgg aaagtccgtg gtttgtgagg cagtaatcag agaggaagtt 780
gtccacaagg ttctcaagac caacgttcag tcactcgtgg agttgaatgt gatcaagaac 840
cttgctggct cagcagttgc tggtgctctt gggggtttca acgcccacgc aagcaacatc 900
gtaacggcta tcttcattgc cactggtcag gatcctgcac agaatgtgga gagctcacag 960
tgtatcacta tgttggaagc tgtaaatgat ggcagagacc ttcacatctc cgttacaatg 1020
ccatctatcg aggtgggcac agttggtgga ggcacgcagc tggcctcaca gtcggcctgc 1080
ttggacctac tgggcgtcaa aggcgccaac agggaatctc cggggtcgaa cgctaggctg 1140
ctggccacgg tggtggctgg tgccgtccta gctggggagc tgtccctcat ctccgcccaa 1200
gctgccggcc atctggtcca gagccacatg aaatacaaca gatccagcaa ggacatgtcc 1260
aagatcgcct gctga 1275
<210> 16
<211> 424
<212> PRT
<213> 糙伏毛燕麦（Avena strigosa）
<220>
<221> misc_feature
<223> AstHMGR（糙伏毛燕麦（Avena strigosa）截短的HMG-CoA还原酶）转化的核苷酸序列
<400> 16
Met Ala Pro Glu Lys Met Pro Glu Glu Asp Glu Glu Ile Val Ala Gly
1 5 10 15
Val Val Ala Gly Lys Ile Pro Ser Tyr Val Leu Glu Thr Arg Leu Gly
20 25 30
Asp Cys Arg Arg Ala Ala Gly Ile Arg Arg Glu Ala Leu Arg Arg Ile
35 40 45
Thr Gly Arg Glu Ile Asp Gly Leu Pro Leu Asp Gly Phe Asp Tyr Asp
50 55 60
Ser Ile Leu Gly Gln Cys Cys Glu Met Pro Val Gly Tyr Val Gln Leu
65 70 75 80
Pro Val Gly Val Ala Gly Pro Leu Val Leu Asp Gly Arg Arg Ile Tyr
85 90 95
Val Pro Met Ala Thr Thr Glu Gly Cys Leu Ile Ala Ser Thr Asn Arg
100 105 110
Gly Cys Lys Ala Ile Ala Glu Ser Gly Gly Ala Ser Ser Val Val Tyr
115 120 125
Arg Asp Gly Met Thr Arg Ala Pro Val Ala Arg Phe Pro Ser Ala Arg
130 135 140
Arg Ala Ala Glu Leu Lys Gly Phe Leu Glu Asn Pro Ala Asn Tyr Asp
145 150 155 160
Thr Leu Ser Val Val Phe Asn Arg Ser Ser Arg Phe Ala Arg Leu Gln
165 170 175
Gly Val Lys Cys Ala Met Ala Gly Arg Asn Leu Tyr Met Arg Phe Thr
180 185 190
Cys Ser Thr Gly Asp Ala Met Gly Met Asn Met Val Ser Lys Gly Val
195 200 205
Gln Asn Val Leu Asp Tyr Leu Gln Glu Asp Phe Pro Asp Met Asp Val
210 215 220
Val Ser Ile Ser Gly Asn Phe Cys Ser Asp Lys Lys Ser Ala Ala Val
225 230 235 240
Asn Trp Ile Glu Gly Arg Gly Lys Ser Val Val Cys Glu Ala Val Ile
245 250 255
Arg Glu Glu Val Val His Lys Val Leu Lys Thr Asn Val Gln Ser Leu
260 265 270
Val Glu Leu Asn Val Ile Lys Asn Leu Ala Gly Ser Ala Val Ala Gly
275 280 285
Ala Leu Gly Gly Phe Asn Ala His Ala Ser Asn Ile Val Thr Ala Ile
290 295 300
Phe Ile Ala Thr Gly Gln Asp Pro Ala Gln Asn Val Glu Ser Ser Gln
305 310 315 320
Cys Ile Thr Met Leu Glu Ala Val Asn Asp Gly Arg Asp Leu His Ile
325 330 335
Ser Val Thr Met Pro Ser Ile Glu Val Gly Thr Val Gly Gly Gly Thr
340 345 350
Gln Leu Ala Ser Gln Ser Ala Cys Leu Asp Leu Leu Gly Val Lys Gly
355 360 365
Ala Asn Arg Glu Ser Pro Gly Ser Asn Ala Arg Leu Leu Ala Thr Val
370 375 380
Val Ala Gly Ala Val Leu Ala Gly Glu Leu Ser Leu Ile Ser Ala Gln
385 390 395 400
Ala Ala Gly His Leu Val Gln Ser His Met Lys Tyr Asn Arg Ser Ser
405 410 415
Lys Asp Met Ser Lys Ile Ala Cys
420
<210> 17
<211> 2277
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 18的酶的核苷酸
<400> 17
atgtggaggc tgaagatagc agaaggtggt tccgatccat atctgttcag cacaaacaac 60
ttcgtgggtc gccagacatg ggagttcgaa ccggaggccg gcacacctga ggagcgagca 120
gaggtcgaag ctgcccgcca aaacttttac aacaaccgtt accaggtcaa gccctgtgac 180
gacctccttt ggagatatca gttcctgaga gagaagaatt tcaaacaaac aataccgcct 240
gtcaaggttg aagatggcca agaaattact tatgagatgg ccacaacctc aatgcagagg 300
gcggcccgtc acctatcagc cttgcaggcc agcgatggcc attggccagc tcaaattgct 360
ggccccttgt tcttcatgcc acccttggtc ttttgtgtgt acattactgg gcatcttaat 420
acagtattcc catctgaaca tcgcaaagaa atccttcgtt acatgtacta tcaccagaac 480
gaagatggtg ggtggggact gcacatagag ggtcacagca ccatgttttg cacagcactc 540
aactacattt gtatgcgtat ccttggggaa ggaccagagg ggggtcaaga caatgcttgt 600
gccagagcac gaatgtggat tcttgatcat ggtggtgtaa cacatattcc atcttgggga 660
aagacctggc tttcgatact tggtctattt gagtggtctg gaagcaatcc aatgcctcca 720
gagttttgga tccttccttc atttcttcct atgcatccag caaaaatgtg gtgctattgc 780
cggatggttt acatgcccat gtcttattta tatgggaaaa ggtttgttgg cccaatcacg 840
cctctcattg ttcagttaag agaggaaata cacactcaaa attaccatga aatcaactgg 900
aagtcagtcc gccatctatg tgcaaaggag gatatctact atccccatcc actcatccaa 960
gatttgattt gggacagttt gtacatacta acggagcctc ttctcactcg ctggcccttg 1020
aacaagttgg tgcgggagag ggctctccaa gtaacaatga agcatatcca ctatgaagat 1080
gaaaatagtc gatacataac cattggatgt gtggaaaagg tgttatgtat gcttgcttgt 1140
tgggttgatg atccaaatgg agatgctttc aagaagcacc ttgctcgagt cccagattac 1200
gtatgggtct ctgaagatgg aattactatg cagagttttg gtagtcaaga atgggatgct 1260
ggctttgccg tccaggctct gcttgcttct aatcttaccg aggaacttgg ccctgctctt 1320
gccaaaggac atgacttcat aaagcaatct caggttaagg acaatccttc aggtgacttc 1380
aaaagcatgt atcgtcacat ttctagagga tcatggacct tctctgacca agatcatgga 1440
tggcaagttt ctgattgcac tgcagaaggt ctgaagtgtt gcctgctttt gtcgatgttg 1500
ccaccagaaa ttgttggtga aaaaatggaa ccacaaaggc tatttgattc tgtcaatgtg 1560
ctgctctctc tacagagcaa aaaaggtggt ttagctgcct gggagccagc aggggcgcaa 1620
gattggttgg aattactcaa tcccacagaa ttttttgcgg acattgtcgt tgagcatgaa 1680
tatgttgaat gtactggatc agcaattcag gcattagttt tgttcaagaa gctgtatccg 1740
gggcacagga aaaaagagat tgacagtttc attacaaatg ctgtccggtt ccttgagaat 1800
acacaaacgg cagatggctc ttggtatgga aactggggag tttgcttcac ctatggttgt 1860
tggttcgcac tgggagggct agcagcagct ggcaagactt acaacaactg tcctgcaata 1920
cgcaaagctg ttaatttcct acttacaaca caaagagaag acggtggttg gggagaaagc 1980
tatctttcaa gcccaaaaaa gatatatgta cccctggaag gaagccgatc aaatgtggta 2040
catactgcat gggctatgat gggtctaatt catgctgggc aggctgaaag agactcaact 2100
cctcttcatc gtgcagcaaa gttgatcatc aattatcaac tagaaaatgg cgattggccg 2160
caacaggaaa tcactggagt attcatgaaa aactgcatgt tacattaccc tatgtacaga 2220
aacatctacc caatgtgggc tcttgcagaa taccggaggc gggttccatt gccttaa 2277
<210> 18
<211> 758
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 参与从2,3-氧化鲨烯制备β-香树素的酶（QsbAS）
<400> 18
Met Trp Arg Leu Lys Ile Ala Glu Gly Gly Ser Asp Pro Tyr Leu Phe
1 5 10 15
Ser Thr Asn Asn Phe Val Gly Arg Gln Thr Trp Glu Phe Glu Pro Glu
20 25 30
Ala Gly Thr Pro Glu Glu Arg Ala Glu Val Glu Ala Ala Arg Gln Asn
35 40 45
Phe Tyr Asn Asn Arg Tyr Gln Val Lys Pro Cys Asp Asp Leu Leu Trp
50 55 60
Arg Tyr Gln Phe Leu Arg Glu Lys Asn Phe Lys Gln Thr Ile Pro Pro
65 70 75 80
Val Lys Val Glu Asp Gly Gln Glu Ile Thr Tyr Glu Met Ala Thr Thr
85 90 95
Ser Met Gln Arg Ala Ala Arg His Leu Ser Ala Leu Gln Ala Ser Asp
100 105 110
Gly His Trp Pro Ala Gln Ile Ala Gly Pro Leu Phe Phe Met Pro Pro
115 120 125
Leu Val Phe Cys Val Tyr Ile Thr Gly His Leu Asn Thr Val Phe Pro
130 135 140
Ser Glu His Arg Lys Glu Ile Leu Arg Tyr Met Tyr Tyr His Gln Asn
145 150 155 160
Glu Asp Gly Gly Trp Gly Leu His Ile Glu Gly His Ser Thr Met Phe
165 170 175
Cys Thr Ala Leu Asn Tyr Ile Cys Met Arg Ile Leu Gly Glu Gly Pro
180 185 190
Glu Gly Gly Gln Asp Asn Ala Cys Ala Arg Ala Arg Met Trp Ile Leu
195 200 205
Asp His Gly Gly Val Thr His Ile Pro Ser Trp Gly Lys Thr Trp Leu
210 215 220
Ser Ile Leu Gly Leu Phe Glu Trp Ser Gly Ser Asn Pro Met Pro Pro
225 230 235 240
Glu Phe Trp Ile Leu Pro Ser Phe Leu Pro Met His Pro Ala Lys Met
245 250 255
Trp Cys Tyr Cys Arg Met Val Tyr Met Pro Met Ser Tyr Leu Tyr Gly
260 265 270
Lys Arg Phe Val Gly Pro Ile Thr Pro Leu Ile Val Gln Leu Arg Glu
275 280 285
Glu Ile His Thr Gln Asn Tyr His Glu Ile Asn Trp Lys Ser Val Arg
290 295 300
His Leu Cys Ala Lys Glu Asp Ile Tyr Tyr Pro His Pro Leu Ile Gln
305 310 315 320
Asp Leu Ile Trp Asp Ser Leu Tyr Ile Leu Thr Glu Pro Leu Leu Thr
325 330 335
Arg Trp Pro Leu Asn Lys Leu Val Arg Glu Arg Ala Leu Gln Val Thr
340 345 350
Met Lys His Ile His Tyr Glu Asp Glu Asn Ser Arg Tyr Ile Thr Ile
355 360 365
Gly Cys Val Glu Lys Val Leu Cys Met Leu Ala Cys Trp Val Asp Asp
370 375 380
Pro Asn Gly Asp Ala Phe Lys Lys His Leu Ala Arg Val Pro Asp Tyr
385 390 395 400
Val Trp Val Ser Glu Asp Gly Ile Thr Met Gln Ser Phe Gly Ser Gln
405 410 415
Glu Trp Asp Ala Gly Phe Ala Val Gln Ala Leu Leu Ala Ser Asn Leu
420 425 430
Thr Glu Glu Leu Gly Pro Ala Leu Ala Lys Gly His Asp Phe Ile Lys
435 440 445
Gln Ser Gln Val Lys Asp Asn Pro Ser Gly Asp Phe Lys Ser Met Tyr
450 455 460
Arg His Ile Ser Arg Gly Ser Trp Thr Phe Ser Asp Gln Asp His Gly
465 470 475 480
Trp Gln Val Ser Asp Cys Thr Ala Glu Gly Leu Lys Cys Cys Leu Leu
485 490 495
Leu Ser Met Leu Pro Pro Glu Ile Val Gly Glu Lys Met Glu Pro Gln
500 505 510
Arg Leu Phe Asp Ser Val Asn Val Leu Leu Ser Leu Gln Ser Lys Lys
515 520 525
Gly Gly Leu Ala Ala Trp Glu Pro Ala Gly Ala Gln Asp Trp Leu Glu
530 535 540
Leu Leu Asn Pro Thr Glu Phe Phe Ala Asp Ile Val Val Glu His Glu
545 550 555 560
Tyr Val Glu Cys Thr Gly Ser Ala Ile Gln Ala Leu Val Leu Phe Lys
565 570 575
Lys Leu Tyr Pro Gly His Arg Lys Lys Glu Ile Asp Ser Phe Ile Thr
580 585 590
Asn Ala Val Arg Phe Leu Glu Asn Thr Gln Thr Ala Asp Gly Ser Trp
595 600 605
Tyr Gly Asn Trp Gly Val Cys Phe Thr Tyr Gly Cys Trp Phe Ala Leu
610 615 620
Gly Gly Leu Ala Ala Ala Gly Lys Thr Tyr Asn Asn Cys Pro Ala Ile
625 630 635 640
Arg Lys Ala Val Asn Phe Leu Leu Thr Thr Gln Arg Glu Asp Gly Gly
645 650 655
Trp Gly Glu Ser Tyr Leu Ser Ser Pro Lys Lys Ile Tyr Val Pro Leu
660 665 670
Glu Gly Ser Arg Ser Asn Val Val His Thr Ala Trp Ala Met Met Gly
675 680 685
Leu Ile His Ala Gly Gln Ala Glu Arg Asp Ser Thr Pro Leu His Arg
690 695 700
Ala Ala Lys Leu Ile Ile Asn Tyr Gln Leu Glu Asn Gly Asp Trp Pro
705 710 715 720
Gln Gln Glu Ile Thr Gly Val Phe Met Lys Asn Cys Met Leu His Tyr
725 730 735
Pro Met Tyr Arg Asn Ile Tyr Pro Met Trp Ala Leu Ala Glu Tyr Arg
740 745 750
Arg Arg Val Pro Leu Pro
755
<210> 19
<211> 1443
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 20的酶的核苷酸
<400> 19
atggagcact tgtatctctc ccttgtgctc ctgtttgttt cctcaatctc cctctccctc 60
ttcttcctgt tctacaaaca caaatctatg ttcaccgggg ccaacctacc acctggtaaa 120
atcggttacc cattgatcgg agagagcttg gagttcttgt ccacgggatg gaagggccac 180
ccggagaaat tcatcttcga tcgcatgagc aagtactcat cccaaatctt caagacctcg 240
attttagggg aaccaacggc ggtgttcccg ggagccgtat gcaacaagtt cctcttctcc 300
aacgagaaca agctggtgaa tgcatggtgg cctgcctccg tggacaagat ctttccttcc 360
tcactccaga catcctccaa agaagaggcc aagaagatga ggaagttgct tcctcagttt 420
ctcaagcccg aagctctgca ccgctacatt ggtattatgg attctattgc ccagagacac 480
tttgccgata gctgggaaaa caaaaaccaa gtcattgtct ttcctctagc aaagaggtat 540
actttctggc tggcttgccg tttgttcatt agcgtcgagg atccgaccca cgtatccaga 600
tttgctgacc cgttccaact tttggccgcc ggaatcatat caatcccaat cgacttgcca 660
gggacaccgt tccgcaaggc aatcaatgcg tcccagttca tcaggaagga attgttggcc 720
atcatcaggc agagaaagat cgatttgggt gaagggaagg catctccgac gcaggacata 780
ctgtctcaca tgttgctcac atgcgacgag aacggacaat acatgaatga attggacatt 840
gccgacaaga ttcttggctt gttggtcggc ggacatgaca ctgccagtgc cgcttgcact 900
ttcattgtca agttcctcgc tgagcttccc cacatttatg aacaagtcta caaggagcaa 960
atggagattg caaaatcaaa agtgccagga gagttgttga attgggagga catccaaaag 1020
atgaaatatt cgtggaacgt agcttgtgaa gtgatgagac ttgcccctcc actccaagga 1080
gctttcaggg aagccattac tgacttcgtc ttcaacggtt tctccattcc aaaaggctgg 1140
aagttgtact ggagcgcaaa ttccacccac aaaagtccgg attatttccc tgagcccgac 1200
aagttcgacc caactagatt cgaaggaaat ggacctgcgc cttacacctt tgttccattt 1260
gggggaggac ccaggatgtg cccgggcaaa gagtatgccc gattggaaat acttgtgttc 1320
atgcataact tggtgaagag gttcaagtgg gagaaattgg ttcctgatga aaagattgtg 1380
gttgatccaa tgcccattcc agcaaagggt cttcctgttc gcctttatcc tcacaaagct 1440
tga 1443
<210> 20
<211> 480
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 参与从β-香树素制备齐墩果酸的酶（QsCYP716-C-28）
<400> 20
Met Glu His Leu Tyr Leu Ser Leu Val Leu Leu Phe Val Ser Ser Ile
1 5 10 15
Ser Leu Ser Leu Phe Phe Leu Phe Tyr Lys His Lys Ser Met Phe Thr
20 25 30
Gly Ala Asn Leu Pro Pro Gly Lys Ile Gly Tyr Pro Leu Ile Gly Glu
35 40 45
Ser Leu Glu Phe Leu Ser Thr Gly Trp Lys Gly His Pro Glu Lys Phe
50 55 60
Ile Phe Asp Arg Met Ser Lys Tyr Ser Ser Gln Ile Phe Lys Thr Ser
65 70 75 80
Ile Leu Gly Glu Pro Thr Ala Val Phe Pro Gly Ala Val Cys Asn Lys
85 90 95
Phe Leu Phe Ser Asn Glu Asn Lys Leu Val Asn Ala Trp Trp Pro Ala
100 105 110
Ser Val Asp Lys Ile Phe Pro Ser Ser Leu Gln Thr Ser Ser Lys Glu
115 120 125
Glu Ala Lys Lys Met Arg Lys Leu Leu Pro Gln Phe Leu Lys Pro Glu
130 135 140
Ala Leu His Arg Tyr Ile Gly Ile Met Asp Ser Ile Ala Gln Arg His
145 150 155 160
Phe Ala Asp Ser Trp Glu Asn Lys Asn Gln Val Ile Val Phe Pro Leu
165 170 175
Ala Lys Arg Tyr Thr Phe Trp Leu Ala Cys Arg Leu Phe Ile Ser Val
180 185 190
Glu Asp Pro Thr His Val Ser Arg Phe Ala Asp Pro Phe Gln Leu Leu
195 200 205
Ala Ala Gly Ile Ile Ser Ile Pro Ile Asp Leu Pro Gly Thr Pro Phe
210 215 220
Arg Lys Ala Ile Asn Ala Ser Gln Phe Ile Arg Lys Glu Leu Leu Ala
225 230 235 240
Ile Ile Arg Gln Arg Lys Ile Asp Leu Gly Glu Gly Lys Ala Ser Pro
245 250 255
Thr Gln Asp Ile Leu Ser His Met Leu Leu Thr Cys Asp Glu Asn Gly
260 265 270
Gln Tyr Met Asn Glu Leu Asp Ile Ala Asp Lys Ile Leu Gly Leu Leu
275 280 285
Val Gly Gly His Asp Thr Ala Ser Ala Ala Cys Thr Phe Ile Val Lys
290 295 300
Phe Leu Ala Glu Leu Pro His Ile Tyr Glu Gln Val Tyr Lys Glu Gln
305 310 315 320
Met Glu Ile Ala Lys Ser Lys Val Pro Gly Glu Leu Leu Asn Trp Glu
325 330 335
Asp Ile Gln Lys Met Lys Tyr Ser Trp Asn Val Ala Cys Glu Val Met
340 345 350
Arg Leu Ala Pro Pro Leu Gln Gly Ala Phe Arg Glu Ala Ile Thr Asp
355 360 365
Phe Val Phe Asn Gly Phe Ser Ile Pro Lys Gly Trp Lys Leu Tyr Trp
370 375 380
Ser Ala Asn Ser Thr His Lys Ser Pro Asp Tyr Phe Pro Glu Pro Asp
385 390 395 400
Lys Phe Asp Pro Thr Arg Phe Glu Gly Asn Gly Pro Ala Pro Tyr Thr
405 410 415
Phe Val Pro Phe Gly Gly Gly Pro Arg Met Cys Pro Gly Lys Glu Tyr
420 425 430
Ala Arg Leu Glu Ile Leu Val Phe Met His Asn Leu Val Lys Arg Phe
435 440 445
Lys Trp Glu Lys Leu Val Pro Asp Glu Lys Ile Val Val Asp Pro Met
450 455 460
Pro Ile Pro Ala Lys Gly Leu Pro Val Arg Leu Tyr Pro His Lys Ala
465 470 475 480
<210> 21
<211> 1506
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 22的酶的核苷酸
<400> 21
atgatatata ataatgatag taatgataat gaattagtaa tcagctcagt tcagcaacca 60
tccatggatc ctttcttcat ttttggctta cttctcttgg ctctctttct ctctgtttct 120
tttcttctct acctttcccg tagagcctat gcttctctcc ccaaccctcc gccggggaag 180
ctcggcttcc ccgtcgtcgg cgagagtctc gaatttctct ccacccgacg caaaggtgtt 240
cctgagaaat tcgtcttcga cagaatggcc aaatactgtc gggatgtctt taagacatca 300
atattgggag caaccaccgc cgtcatgtgc ggcaccgccg gtaacaaatt cttgttctcc 360
aacgagaaaa aacacgtcac tggttggtgg ccgaaatctg tagagctgat tttcccaacc 420
tcacttgaga aatcatccaa cgaagaatcc atcatgatga aacaattcct tcccaacttc 480
ttgaaaccag aacctttgca gaagtacata cccgttatgg acataattac ccaaagacac 540
ttcaatacaa gctgggaagg acgcaacgtg gtcaaagtgt ttcctacggc tgccgaattc 600
accacgttgc tggcttgtcg ggtattcctc agtgttgagg atcccattga agtagccaag 660
atttcagagc catttgaaat cttagctgct gggtttcttt caatacccat aaatcttccg 720
ggtaccaaat taaataaagc ggttaaggca gcggatcaga ttagagacgc aattgtacag 780
attttgaaac ggagaagggt tgaaattgcg gagaataaag caaatggaat gcaagatata 840
gcgtccatgt tgttgacgac accaactaat gctgggtttt atatgaccga ggctcacatt 900
tctgagaaaa ttttgggtat gattgttggt ggccgtgata ctgctagtac tgttatcacc 960
ttcatcatca agtatttggc agagaatcct gaaatttata ataaggtcta tgaggagcaa 1020
atggaagtgg taaagtcaaa gaaaccaggt gagttgctga actgggaaga tgtgcagaaa 1080
atgaagtact cttggtgcgt agcatgtgaa gctatgcgac ttgctcctcc tgttcaaggt 1140
ggtttcaagg tggccattaa tgactttgtg tattctgggt tcaacattcg caagggttgg 1200
aagttatatt ggagtgccat tgcaacacac atgaatccag aatatttccc agaacctgag 1260
aaattcaacc cctcaaggtt tgaagggaag ggaccagtac cttacagctt cgtacccttc 1320
ggaggcggac ctcggatgtg tcccgggaaa gagtattccc ggctggaaac acttgttttc 1380
atgcatcatt tggtgacgag gtacaattgg gagaaagtgt atcccacaga gaagataaca 1440
gtggatccaa tgccattccc tgtcaacggc ctccccattc gccttattcc tcacaagcac 1500
caatga 1506
<210> 22
<211> 501
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 参与从齐墩果酸制备刺囊酸的酶（QsCYP716-C-16alpha）
<400> 22
Met Ile Tyr Asn Asn Asp Ser Asn Asp Asn Glu Leu Val Ile Ser Ser
1 5 10 15
Val Gln Gln Pro Ser Met Asp Pro Phe Phe Ile Phe Gly Leu Leu Leu
20 25 30
Leu Ala Leu Phe Leu Ser Val Ser Phe Leu Leu Tyr Leu Ser Arg Arg
35 40 45
Ala Tyr Ala Ser Leu Pro Asn Pro Pro Pro Gly Lys Leu Gly Phe Pro
50 55 60
Val Val Gly Glu Ser Leu Glu Phe Leu Ser Thr Arg Arg Lys Gly Val
65 70 75 80
Pro Glu Lys Phe Val Phe Asp Arg Met Ala Lys Tyr Cys Arg Asp Val
85 90 95
Phe Lys Thr Ser Ile Leu Gly Ala Thr Thr Ala Val Met Cys Gly Thr
100 105 110
Ala Gly Asn Lys Phe Leu Phe Ser Asn Glu Lys Lys His Val Thr Gly
115 120 125
Trp Trp Pro Lys Ser Val Glu Leu Ile Phe Pro Thr Ser Leu Glu Lys
130 135 140
Ser Ser Asn Glu Glu Ser Ile Met Met Lys Gln Phe Leu Pro Asn Phe
145 150 155 160
Leu Lys Pro Glu Pro Leu Gln Lys Tyr Ile Pro Val Met Asp Ile Ile
165 170 175
Thr Gln Arg His Phe Asn Thr Ser Trp Glu Gly Arg Asn Val Val Lys
180 185 190
Val Phe Pro Thr Ala Ala Glu Phe Thr Thr Leu Leu Ala Cys Arg Val
195 200 205
Phe Leu Ser Val Glu Asp Pro Ile Glu Val Ala Lys Ile Ser Glu Pro
210 215 220
Phe Glu Ile Leu Ala Ala Gly Phe Leu Ser Ile Pro Ile Asn Leu Pro
225 230 235 240
Gly Thr Lys Leu Asn Lys Ala Val Lys Ala Ala Asp Gln Ile Arg Asp
245 250 255
Ala Ile Val Gln Ile Leu Lys Arg Arg Arg Val Glu Ile Ala Glu Asn
260 265 270
Lys Ala Asn Gly Met Gln Asp Ile Ala Ser Met Leu Leu Thr Thr Pro
275 280 285
Thr Asn Ala Gly Phe Tyr Met Thr Glu Ala His Ile Ser Glu Lys Ile
290 295 300
Leu Gly Met Ile Val Gly Gly Arg Asp Thr Ala Ser Thr Val Ile Thr
305 310 315 320
Phe Ile Ile Lys Tyr Leu Ala Glu Asn Pro Glu Ile Tyr Asn Lys Val
325 330 335
Tyr Glu Glu Gln Met Glu Val Val Lys Ser Lys Lys Pro Gly Glu Leu
340 345 350
Leu Asn Trp Glu Asp Val Gln Lys Met Lys Tyr Ser Trp Cys Val Ala
355 360 365
Cys Glu Ala Met Arg Leu Ala Pro Pro Val Gln Gly Gly Phe Lys Val
370 375 380
Ala Ile Asn Asp Phe Val Tyr Ser Gly Phe Asn Ile Arg Lys Gly Trp
385 390 395 400
Lys Leu Tyr Trp Ser Ala Ile Ala Thr His Met Asn Pro Glu Tyr Phe
405 410 415
Pro Glu Pro Glu Lys Phe Asn Pro Ser Arg Phe Glu Gly Lys Gly Pro
420 425 430
Val Pro Tyr Ser Phe Val Pro Phe Gly Gly Gly Pro Arg Met Cys Pro
435 440 445
Gly Lys Glu Tyr Ser Arg Leu Glu Thr Leu Val Phe Met His His Leu
450 455 460
Val Thr Arg Tyr Asn Trp Glu Lys Val Tyr Pro Thr Glu Lys Ile Thr
465 470 475 480
Val Asp Pro Met Pro Phe Pro Val Asn Gly Leu Pro Ile Arg Leu Ile
485 490 495
Pro His Lys His Gln
500
<210> 23
<211> 1524
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 24的酶的核苷酸
<400> 23
atgtggttca cagtaggatt ggtcttggtt ttcgccctat tcatacgtct ctacagcagt 60
ctgtggttga agcctcgtgc aactcggatt aagcttagca atcaaggaat taaaggtcca 120
aaaccagcat ttcttctggg taatgttgca gagatgagaa gatttcaatc taagcttcca 180
aaatctgaac tcaaacaagg ccaagtttct catgattggg cttctaaatc tctgtttcca 240
tttttcagtc tttggtccca gaaatacgga aatacgttcg tgttctcatt ggggaacata 300
caggtgctct atgtttctga tcatgagttg gtgaaagaaa ttaatcagaa tacctcttta 360
gatttgggca aacccaagta cctgcagaag gagcgtggcc ctttgctggg acaaggtatt 420
ttgacctcca atggacagct ttgggcgtac cagagaaaaa tcatgactcc tgaactctac 480
aaggagaaaa tcaagggcat gtgcgagttg atggtggaat ctgtagcttg gttggttgag 540
gaatggggaa cgaagatcca agctgagggt ggggcagcag acattagaat agacgaggat 600
cttagaagct tctctggtga tgtaatttca aaagcttgtt ttgggagctg ctatgccgga 660
gggagggaaa tctttcttag gctcagagct cttcaacacc aaattgcttc caaagcctta 720
ctcatgggct tccctggatt aaagtacctg cccattaaga gcaacagaga gatatggaga 780
ttggagaagg agatcttcca gctgattatg aagctggctg aagatagaaa aaaagaacaa 840
catgagagag acctattaca gattataatt gagggagcta aaagtagtga tctgagttcg 900
gaagcaatgg caaaattcat tgtggacaac tgcaagaatg tctacttggc tggccatgaa 960
actactgcaa tgtctgctgg ttggactttg cttctcttgg ctaatcatcc tgagtggcaa 1020
gcccgtgtcc gtgatgagat tttacaagtc accgagggcc gcaatcctga ttttgacatg 1080
ctgcacaaga tgaaactgtt aacaatggta attcaggagg cactgcgact ctacccaaca 1140
gtcatattca tgtcaagaga agcattggaa gatattaatg ttggaaacat ccaagttcca 1200
aaaggtgtta acatatggat acctgtggta aatcttcaaa gggacacaac ggtatggggt 1260
gcagacgcaa acgagtttaa tcctgaaagg tttgccaatg gagttaacaa ttcatgcaag 1320
gttccacaac tttacctacc atttggagct ggacctcgca tttgtcctgg aattaatctg 1380
gccatgactg agatcaagat acttctgtgt atcctgctca ccaagttttc gttttcagtt 1440
tcacccaact atcgccactc accggtgttt aaattggtgc ttgagcctga aaatggaatc 1500
aatgtcatca tgaagaagct ctaa 1524
<210> 24
<211> 507
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 参与从刺囊酸制备皂树皮酸的酶（QsCYP714-C-23）
<400> 24
Met Trp Phe Thr Val Gly Leu Val Leu Val Phe Ala Leu Phe Ile Arg
1 5 10 15
Leu Tyr Ser Ser Leu Trp Leu Lys Pro Arg Ala Thr Arg Ile Lys Leu
20 25 30
Ser Asn Gln Gly Ile Lys Gly Pro Lys Pro Ala Phe Leu Leu Gly Asn
35 40 45
Val Ala Glu Met Arg Arg Phe Gln Ser Lys Leu Pro Lys Ser Glu Leu
50 55 60
Lys Gln Gly Gln Val Ser His Asp Trp Ala Ser Lys Ser Leu Phe Pro
65 70 75 80
Phe Phe Ser Leu Trp Ser Gln Lys Tyr Gly Asn Thr Phe Val Phe Ser
85 90 95
Leu Gly Asn Ile Gln Val Leu Tyr Val Ser Asp His Glu Leu Val Lys
100 105 110
Glu Ile Asn Gln Asn Thr Ser Leu Asp Leu Gly Lys Pro Lys Tyr Leu
115 120 125
Gln Lys Glu Arg Gly Pro Leu Leu Gly Gln Gly Ile Leu Thr Ser Asn
130 135 140
Gly Gln Leu Trp Ala Tyr Gln Arg Lys Ile Met Thr Pro Glu Leu Tyr
145 150 155 160
Lys Glu Lys Ile Lys Gly Met Cys Glu Leu Met Val Glu Ser Val Ala
165 170 175
Trp Leu Val Glu Glu Trp Gly Thr Lys Ile Gln Ala Glu Gly Gly Ala
180 185 190
Ala Asp Ile Arg Ile Asp Glu Asp Leu Arg Ser Phe Ser Gly Asp Val
195 200 205
Ile Ser Lys Ala Cys Phe Gly Ser Cys Tyr Ala Gly Gly Arg Glu Ile
210 215 220
Phe Leu Arg Leu Arg Ala Leu Gln His Gln Ile Ala Ser Lys Ala Leu
225 230 235 240
Leu Met Gly Phe Pro Gly Leu Lys Tyr Leu Pro Ile Lys Ser Asn Arg
245 250 255
Glu Ile Trp Arg Leu Glu Lys Glu Ile Phe Gln Leu Ile Met Lys Leu
260 265 270
Ala Glu Asp Arg Lys Lys Glu Gln His Glu Arg Asp Leu Leu Gln Ile
275 280 285
Ile Ile Glu Gly Ala Lys Ser Ser Asp Leu Ser Ser Glu Ala Met Ala
290 295 300
Lys Phe Ile Val Asp Asn Cys Lys Asn Val Tyr Leu Ala Gly His Glu
305 310 315 320
Thr Thr Ala Met Ser Ala Gly Trp Thr Leu Leu Leu Leu Ala Asn His
325 330 335
Pro Glu Trp Gln Ala Arg Val Arg Asp Glu Ile Leu Gln Val Thr Glu
340 345 350
Gly Arg Asn Pro Asp Phe Asp Met Leu His Lys Met Lys Leu Leu Thr
355 360 365
Met Val Ile Gln Glu Ala Leu Arg Leu Tyr Pro Thr Val Ile Phe Met
370 375 380
Ser Arg Glu Ala Leu Glu Asp Ile Asn Val Gly Asn Ile Gln Val Pro
385 390 395 400
Lys Gly Val Asn Ile Trp Ile Pro Val Val Asn Leu Gln Arg Asp Thr
405 410 415
Thr Val Trp Gly Ala Asp Ala Asn Glu Phe Asn Pro Glu Arg Phe Ala
420 425 430
Asn Gly Val Asn Asn Ser Cys Lys Val Pro Gln Leu Tyr Leu Pro Phe
435 440 445
Gly Ala Gly Pro Arg Ile Cys Pro Gly Ile Asn Leu Ala Met Thr Glu
450 455 460
Ile Lys Ile Leu Leu Cys Ile Leu Leu Thr Lys Phe Ser Phe Ser Val
465 470 475 480
Ser Pro Asn Tyr Arg His Ser Pro Val Phe Lys Leu Val Leu Glu Pro
485 490 495
Glu Asn Gly Ile Asn Val Ile Met Lys Lys Leu
500 505
<210> 25
<211> 2142
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 26的酶的核苷酸
<400> 25
atgaaatccc cctctaaccc aaatcagaaa cccatcctcc acacttgtac aattcagcag 60
cctcgtgcta cccttaacaa aattcatagt cttattcatt tctcagccat acttgtccta 120
ttttattacc ggataacccg tctattcttc accgacgatt tcaaggtacc caagttacta 180
tggactctaa tgacaatctc cgagttcatt cttgccttca tttgggttct catccaacct 240
ttccggtggc gaccggtgtc ccgttccgtc ataccagaga atatgccgaa ggacatcagt 300
ttgccggcgg tggacgtgtt tgtatgcaca gctgaccctc aaaaagaacc cacagtggag 360
gtgatgaaca caattttatc agccatggct ttagactacc cggcggagaa gctcgccgtg 420
tatctttccg atgatggggg ttctgctgtc accttatatg ctataaaaga agcttgttgt 480
tttgctaaga tgtggcttcc gttttgtaac aagtatggga tcaaatcaag gtgtcccgag 540
gcttattttt caaagcttgc cgctgacgag tggcttcacc ggagtgtgga attcgtggca 600
gaagaaaagg aggtcaaggc taattatgaa gagttcaaga gaaatgtgca gaaatttggt 660
gagcaacaag aaaacagtcg tgttgtgcat gatcgtcacc ctcatgttga gattatacac 720
aataattgga ataacgaaga ccaagctcat gagatgccac tccttgttta tgtctctcgt 780
gaaagaagac catctcacca tcctcgattc aaagctggag ctcttaacac ccttcttcga 840
gtttctggca tcatcagcaa cagcccctac atactggttc tagactgtga catgtactgc 900
aatgacccaa cctcagctag acaagcaatg tgcttccatc ttgatcccca actgtctaaa 960
aatcttgctt ttgtacaatt ccctcaaata ttctataacg ctagtaagaa tgacgtctat 1020
gatgcccaag tcagggcggc ataccagaca aagtggcagg gtatggatgg acttcaagga 1080
ccaatttttt ctggcactgg cttttactta aagaggaagg caatgtatgg aaaccctgat 1140
caagatgata attgtctact caagccatat aagaaatttg gcatgtctgg agaatttgta 1200
gaatcactta aggtccttaa cgaacaagat ggtacccaga agaaattatt ggatggattt 1260
ttacaagagg ccaaactatt ggcctcgtgt gcctatgaaa caaagacaag ttggggtaaa 1320
gagattggat tctcatatga ctgtttaata gagagcactt tcactggtta tcttttgcac 1380
tgcagagggt ggatatctgt ttatctttat cccaagagac catgtttttt aggatgctgt 1440
cctactgata tgaaggatgc catggttcaa tataccaagt ggatgtctga gctattttca 1500
attgctatct caagattcaa tcctctgctc tatggggtgg caagaatgtc cattcttcaa 1560
agcctgtgtt atggatcctt tacactggcg cctattttgt catttccttt gttcttatat 1620
ggaacggttc ctcaattatg cctcttgaaa ggcatatctt tgtttccaaa ggtttcggac 1680
ccatggtttg ctgtgtttgc agctatcttt gtatcctccc tgtgtcaaca ctggttcgag 1740
gtcctctctt gtgatggtac atttacgact tggtgtaatg aacagcggag ttggcttata 1800
aagtcggttt ccggtagttt gtttggagtt gtgggcgcaa tcttgcagcg gctaggcttg 1860
aagacaaagt ttagtttatc aaacaaagcc atggacaaag aaaagctgga gaaatatgaa 1920
aagggtaaat ttaatttcca aggggctgcc atgttcatgg ttcctgtgtc tattttagtc 1980
atactgaaca cattttgctt cctcggtggg ttttggaaag tgatcataat gaagaatatc 2040
ctggacatgt ttggacaact ttctctctct gcctacgttc tggttctcag ttgtccagtt 2100
cttgaaggga tgttaactag aatcagcaag aaaatggtct ga 2142
<210> 26
<211> 713
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 参与从皂树皮酸制备QA-Mono的酶（QsCSL1）
<400> 26
Met Lys Ser Pro Ser Asn Pro Asn Gln Lys Pro Ile Leu His Thr Cys
1 5 10 15
Thr Ile Gln Gln Pro Arg Ala Thr Leu Asn Lys Ile His Ser Leu Ile
20 25 30
His Phe Ser Ala Ile Leu Val Leu Phe Tyr Tyr Arg Ile Thr Arg Leu
35 40 45
Phe Phe Thr Asp Asp Phe Lys Val Pro Lys Leu Leu Trp Thr Leu Met
50 55 60
Thr Ile Ser Glu Phe Ile Leu Ala Phe Ile Trp Val Leu Ile Gln Pro
65 70 75 80
Phe Arg Trp Arg Pro Val Ser Arg Ser Val Ile Pro Glu Asn Met Pro
85 90 95
Lys Asp Ile Ser Leu Pro Ala Val Asp Val Phe Val Cys Thr Ala Asp
100 105 110
Pro Gln Lys Glu Pro Thr Val Glu Val Met Asn Thr Ile Leu Ser Ala
115 120 125
Met Ala Leu Asp Tyr Pro Ala Glu Lys Leu Ala Val Tyr Leu Ser Asp
130 135 140
Asp Gly Gly Ser Ala Val Thr Leu Tyr Ala Ile Lys Glu Ala Cys Cys
145 150 155 160
Phe Ala Lys Met Trp Leu Pro Phe Cys Asn Lys Tyr Gly Ile Lys Ser
165 170 175
Arg Cys Pro Glu Ala Tyr Phe Ser Lys Leu Ala Ala Asp Glu Trp Leu
180 185 190
His Arg Ser Val Glu Phe Val Ala Glu Glu Lys Glu Val Lys Ala Asn
195 200 205
Tyr Glu Glu Phe Lys Arg Asn Val Gln Lys Phe Gly Glu Gln Gln Glu
210 215 220
Asn Ser Arg Val Val His Asp Arg His Pro His Val Glu Ile Ile His
225 230 235 240
Asn Asn Trp Asn Asn Glu Asp Gln Ala His Glu Met Pro Leu Leu Val
245 250 255
Tyr Val Ser Arg Glu Arg Arg Pro Ser His His Pro Arg Phe Lys Ala
260 265 270
Gly Ala Leu Asn Thr Leu Leu Arg Val Ser Gly Ile Ile Ser Asn Ser
275 280 285
Pro Tyr Ile Leu Val Leu Asp Cys Asp Met Tyr Cys Asn Asp Pro Thr
290 295 300
Ser Ala Arg Gln Ala Met Cys Phe His Leu Asp Pro Gln Leu Ser Lys
305 310 315 320
Asn Leu Ala Phe Val Gln Phe Pro Gln Ile Phe Tyr Asn Ala Ser Lys
325 330 335
Asn Asp Val Tyr Asp Ala Gln Val Arg Ala Ala Tyr Gln Thr Lys Trp
340 345 350
Gln Gly Met Asp Gly Leu Gln Gly Pro Ile Phe Ser Gly Thr Gly Phe
355 360 365
Tyr Leu Lys Arg Lys Ala Met Tyr Gly Asn Pro Asp Gln Asp Asp Asn
370 375 380
Cys Leu Leu Lys Pro Tyr Lys Lys Phe Gly Met Ser Gly Glu Phe Val
385 390 395 400
Glu Ser Leu Lys Val Leu Asn Glu Gln Asp Gly Thr Gln Lys Lys Leu
405 410 415
Leu Asp Gly Phe Leu Gln Glu Ala Lys Leu Leu Ala Ser Cys Ala Tyr
420 425 430
Glu Thr Lys Thr Ser Trp Gly Lys Glu Ile Gly Phe Ser Tyr Asp Cys
435 440 445
Leu Ile Glu Ser Thr Phe Thr Gly Tyr Leu Leu His Cys Arg Gly Trp
450 455 460
Ile Ser Val Tyr Leu Tyr Pro Lys Arg Pro Cys Phe Leu Gly Cys Cys
465 470 475 480
Pro Thr Asp Met Lys Asp Ala Met Val Gln Tyr Thr Lys Trp Met Ser
485 490 495
Glu Leu Phe Ser Ile Ala Ile Ser Arg Phe Asn Pro Leu Leu Tyr Gly
500 505 510
Val Ala Arg Met Ser Ile Leu Gln Ser Leu Cys Tyr Gly Ser Phe Thr
515 520 525
Leu Ala Pro Ile Leu Ser Phe Pro Leu Phe Leu Tyr Gly Thr Val Pro
530 535 540
Gln Leu Cys Leu Leu Lys Gly Ile Ser Leu Phe Pro Lys Val Ser Asp
545 550 555 560
Pro Trp Phe Ala Val Phe Ala Ala Ile Phe Val Ser Ser Leu Cys Gln
565 570 575
His Trp Phe Glu Val Leu Ser Cys Asp Gly Thr Phe Thr Thr Trp Cys
580 585 590
Asn Glu Gln Arg Ser Trp Leu Ile Lys Ser Val Ser Gly Ser Leu Phe
595 600 605
Gly Val Val Gly Ala Ile Leu Gln Arg Leu Gly Leu Lys Thr Lys Phe
610 615 620
Ser Leu Ser Asn Lys Ala Met Asp Lys Glu Lys Leu Glu Lys Tyr Glu
625 630 635 640
Lys Gly Lys Phe Asn Phe Gln Gly Ala Ala Met Phe Met Val Pro Val
645 650 655
Ser Ile Leu Val Ile Leu Asn Thr Phe Cys Phe Leu Gly Gly Phe Trp
660 665 670
Lys Val Ile Ile Met Lys Asn Ile Leu Asp Met Phe Gly Gln Leu Ser
675 680 685
Leu Ser Ala Tyr Val Leu Val Leu Ser Cys Pro Val Leu Glu Gly Met
690 695 700
Leu Thr Arg Ile Ser Lys Lys Met Val
705 710
<210> 27
<211> 2124
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 28的酶的核苷酸
<400> 27
atggcgaccg tctcctccct ccacacttgc actgtacagc aaccccgtgc agccattaat 60
cgaattcaca ttttcttaca ctttattgcc atacttttcc tcttttacta ccgggtcacc 120
ggtcttttct atgacaatgc agtacccact ttagcttggt ctctaatgac cttagctgag 180
ttgattttcg ccttcgtttg ggtgctcagc caagccttcc ggtggcgccc ggtgttgcgt 240
tcagttattc ctgagaggat tcccaaagat gtacgattgc ccgcggtgga tatcttaatt 300
tgtacggctg acccattaaa ggaaccgacg gtggaggtga tgaacactgt cttgtccgcc 360
atggcattgg actatcctgc ggagaatctg gctgtatatc tttctgatga cgggggttct 420
ccggtcacct tatttgctat gaagcaagtg ggtccgtttg ctaagctgtg gcttccgttt 480
tgcaacaagt acggaatcaa aacaaggcat cctgagtctt ttttctcggc atttgcggat 540
gacgaaaggc ttcaccggag tgatgaattc agggcagagg aggaggcgat caaggacaaa 600
tatgaagaat ttaagagaac tatagagaaa tatggtggag aaggaaaaaa tagtcatgtt 660
gtacaagacc ggcctcctca tgtggagatt atacatgaca ctaggaagat tagagagaac 720
agtgaagacc aagctgtgcc tcttcttgtc tacgtctctc gtgagaaaag accatcctac 780
aattctcggt tcaaagcagg agctctgaac acccttcttc gagtttctgg ggtaatcagc 840
aatagcccat atgtattggt gttagactgt gacatgtact gcaatgatcc aacatcagct 900
agacaagcaa tgtgcttcca tcttgatcca caaatgtctc gcactctctc ttttgtacaa 960
ttcccccagg ttttctacaa tgttagtaaa aatgatatct atgatggcca agctagggca 1020
gcctttaaga caaagtggca aggtatggat ggactacgtg ggccactgct ttctggtact 1080
ggcttttatt tgaagaggaa gtccttgtat ggaagtccaa accaagaaga tgattgttta 1140
cttgagcccc ataagaattt tggaaagtgt gacaagctca tagaatcagt aaaggtcatt 1200
tatgaacgtg atgtttcaat aaaggcagat tcatcagatg ccattttgca agatgccaaa 1260
caattagcat cttgtcccta tgaaacaaac acaagctggg gcaaagaggt tgggttctcg 1320
tatgactgct tattagagag tacattcaca ggttatctgt tgcactgcag agggtggaca 1380
tcagtttatc tttatccaaa gaagccatgt ttcttagggt gtactccagt tgatatgaag 1440
gaagccatgg ttcagtatac gaagtggatt tctgaattat ttttacttgc tatctcaaga 1500
ttcaaccctc tgacatttgg gatatccaga atgtccattc tccagagcat gtgttacgga 1560
taccttacaa tcatgcccat tttatctgtt gctatgatct tctatgccac agttcctcaa 1620
ttgtgcctct tgagaggcgt acctctgttt cccaaggttt cagacccatg gtttgcagtg 1680
ttcctagcaa tatttgtgtc ctccctctgt cagcacttaa ttgaagtcct cacgagtgat 1740
ggcacgctca agacttggtg gaatgaacaa agaaattggg tgataaagtc tggttccggt 1800
agcgtatttg gagctctgag tggaatattg aagtggtttg gcatgaagat taaatttggt 1860
ttatcaaaca aagccgtgga caaagaaaag cttgagaaat atgaaaaggg taagtttgat 1920
ttccaagggg ctgccatgtt tatggttccc ttaactatat cagtcatctt gaacacatta 1980
tgccttatcg gtggtttatg gagagtaatc acacttaaaa acttcgaaga gatgtcaggg 2040
cagttcatca tctccttgta ctttctagct ctcagctatc caattcttga agggttacta 2100
agaaaaggca agggaaaggc ctaa 2124
<210> 28
<211> 707
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 参与从皂树皮酸制备QA-Mono的酶（QsCslG2）
<400> 28
Met Ala Thr Val Ser Ser Leu His Thr Cys Thr Val Gln Gln Pro Arg
1 5 10 15
Ala Ala Ile Asn Arg Ile His Ile Phe Leu His Phe Ile Ala Ile Leu
20 25 30
Phe Leu Phe Tyr Tyr Arg Val Thr Gly Leu Phe Tyr Asp Asn Ala Val
35 40 45
Pro Thr Leu Ala Trp Ser Leu Met Thr Leu Ala Glu Leu Ile Phe Ala
50 55 60
Phe Val Trp Val Leu Ser Gln Ala Phe Arg Trp Arg Pro Val Leu Arg
65 70 75 80
Ser Val Ile Pro Glu Arg Ile Pro Lys Asp Val Arg Leu Pro Ala Val
85 90 95
Asp Ile Leu Ile Cys Thr Ala Asp Pro Leu Lys Glu Pro Thr Val Glu
100 105 110
Val Met Asn Thr Val Leu Ser Ala Met Ala Leu Asp Tyr Pro Ala Glu
115 120 125
Asn Leu Ala Val Tyr Leu Ser Asp Asp Gly Gly Ser Pro Val Thr Leu
130 135 140
Phe Ala Met Lys Gln Val Gly Pro Phe Ala Lys Leu Trp Leu Pro Phe
145 150 155 160
Cys Asn Lys Tyr Gly Ile Lys Thr Arg His Pro Glu Ser Phe Phe Ser
165 170 175
Ala Phe Ala Asp Asp Glu Arg Leu His Arg Ser Asp Glu Phe Arg Ala
180 185 190
Glu Glu Glu Ala Ile Lys Asp Lys Tyr Glu Glu Phe Lys Arg Thr Ile
195 200 205
Glu Lys Tyr Gly Gly Glu Gly Lys Asn Ser His Val Val Gln Asp Arg
210 215 220
Pro Pro His Val Glu Ile Ile His Asp Thr Arg Lys Ile Arg Glu Asn
225 230 235 240
Ser Glu Asp Gln Ala Val Pro Leu Leu Val Tyr Val Ser Arg Glu Lys
245 250 255
Arg Pro Ser Tyr Asn Ser Arg Phe Lys Ala Gly Ala Leu Asn Thr Leu
260 265 270
Leu Arg Val Ser Gly Val Ile Ser Asn Ser Pro Tyr Val Leu Val Leu
275 280 285
Asp Cys Asp Met Tyr Cys Asn Asp Pro Thr Ser Ala Arg Gln Ala Met
290 295 300
Cys Phe His Leu Asp Pro Gln Met Ser Arg Thr Leu Ser Phe Val Gln
305 310 315 320
Phe Pro Gln Val Phe Tyr Asn Val Ser Lys Asn Asp Ile Tyr Asp Gly
325 330 335
Gln Ala Arg Ala Ala Phe Lys Thr Lys Trp Gln Gly Met Asp Gly Leu
340 345 350
Arg Gly Pro Leu Leu Ser Gly Thr Gly Phe Tyr Leu Lys Arg Lys Ser
355 360 365
Leu Tyr Gly Ser Pro Asn Gln Glu Asp Asp Cys Leu Leu Glu Pro His
370 375 380
Lys Asn Phe Gly Lys Cys Asp Lys Leu Ile Glu Ser Val Lys Val Ile
385 390 395 400
Tyr Glu Arg Asp Val Ser Ile Lys Ala Asp Ser Ser Asp Ala Ile Leu
405 410 415
Gln Asp Ala Lys Gln Leu Ala Ser Cys Pro Tyr Glu Thr Asn Thr Ser
420 425 430
Trp Gly Lys Glu Val Gly Phe Ser Tyr Asp Cys Leu Leu Glu Ser Thr
435 440 445
Phe Thr Gly Tyr Leu Leu His Cys Arg Gly Trp Thr Ser Val Tyr Leu
450 455 460
Tyr Pro Lys Lys Pro Cys Phe Leu Gly Cys Thr Pro Val Asp Met Lys
465 470 475 480
Glu Ala Met Val Gln Tyr Thr Lys Trp Ile Ser Glu Leu Phe Leu Leu
485 490 495
Ala Ile Ser Arg Phe Asn Pro Leu Thr Phe Gly Ile Ser Arg Met Ser
500 505 510
Ile Leu Gln Ser Met Cys Tyr Gly Tyr Leu Thr Ile Met Pro Ile Leu
515 520 525
Ser Val Ala Met Ile Phe Tyr Ala Thr Val Pro Gln Leu Cys Leu Leu
530 535 540
Arg Gly Val Pro Leu Phe Pro Lys Val Ser Asp Pro Trp Phe Ala Val
545 550 555 560
Phe Leu Ala Ile Phe Val Ser Ser Leu Cys Gln His Leu Ile Glu Val
565 570 575
Leu Thr Ser Asp Gly Thr Leu Lys Thr Trp Trp Asn Glu Gln Arg Asn
580 585 590
Trp Val Ile Lys Ser Gly Ser Gly Ser Val Phe Gly Ala Leu Ser Gly
595 600 605
Ile Leu Lys Trp Phe Gly Met Lys Ile Lys Phe Gly Leu Ser Asn Lys
610 615 620
Ala Val Asp Lys Glu Lys Leu Glu Lys Tyr Glu Lys Gly Lys Phe Asp
625 630 635 640
Phe Gln Gly Ala Ala Met Phe Met Val Pro Leu Thr Ile Ser Val Ile
645 650 655
Leu Asn Thr Leu Cys Leu Ile Gly Gly Leu Trp Arg Val Ile Thr Leu
660 665 670
Lys Asn Phe Glu Glu Met Ser Gly Gln Phe Ile Ile Ser Leu Tyr Phe
675 680 685
Leu Ala Leu Ser Tyr Pro Ile Leu Glu Gly Leu Leu Arg Lys Gly Lys
690 695 700
Gly Lys Ala
705
<210> 29
<211> 1479
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 30的酶的核苷酸
<400> 29
atggtggagt ctccagcaga tcatgatgtg ctcaaaatca ttgtccttcc atgggtaacc 60
tcaggtcaca tgattcccat ggtagatgca gccagactat ttgctatgca tggtgcagat 120
gttaccatca tcaccacccc agctaatgcc cttacattcc agaaatccgt cgaccgtgat 180
ttcaattccg gtcgtttaat cagaactcac acccttaaat tccctgcagc agaagttggt 240
gtacctgaag gagttgaaaa cttcaacaat acttcccctg aaatgacctc caaagtctac 300
cttggagtct caatgctccg agaaccaacc caacaattga ttgaggatct gcgtccagat 360
tgtcttatca ctgatatgtt ctatccttgg gctgtggatg ttgctgacaa attaggcatt 420
ccaaggctaa tttttcaagg tcctggaagt tttggtttgt cagctatgca ttctatcaaa 480
cagtatgagc cctttaagtc agtaacttca gatactgaga cattcccact acctggattg 540
ccgcataagg tagagatgac aaggttgcag ataccaaaat gggttcgtga gccaaatggg 600
tacactcaat tgatgggcag ggtaaaagat tcggagagaa gaagctatgg gtcattggtg 660
aatagctttt atgacttcga aggcccttat gaagagcact ataggaaggc aacaggacag 720
agggtttgga gcattggacc agtttcagtt tgggtgaacc aagatgctgc agataaggtt 780
ggaagaggac aggatcttgt tgctgaagac caaaacagct ggttgaattg gctcaattcc 840
aaagagaaaa actctgttct gtatgtaagt tttgggagca tggccaagtt cccatctgct 900
cagcttcttg aaatagctca tgggcttgaa gcttcaggtc atagtttcat ctgggttgtc 960
agaaaagttg acggggatga tgatgtagac gtgtggcttc cagattttga gaagaaaatg 1020
aaagagaaca acaagggttt catcataagg aattgggcac cacaattgct catattggac 1080
catccagcaa ttggaggttt gctgaatcac agtggatgga attcagtact ggaaggtgct 1140
acagcaggct tgccaatgat cacttggcct ctgtatgccg agcattttta caatgaaagg 1200
ttggttctag atgtgttgaa aattggagta ccagttgggg tgaaggagtg gaagaacttg 1260
catgaggtgg gtgagttggt gagaagggat gcaattgcca aggcaattaa attgttaatg 1320
ggtagtggag aagaagctga ggtaatgagg aaaaaagcca aagagcttgg tgttggagca 1380
aagaaaggta ttcaggttgg aggttcttct cataccaatt tgatagcagt gattgatgag 1440
ttaaagtcac taaagaaatc aagaattcag ggtgtctga 1479
<210> 30
<211> 492
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 参与从QA-Mono制备QA-Di的酶（Qs-3-O-GalT）
<400> 30
Met Val Glu Ser Pro Ala Asp His Asp Val Leu Lys Ile Ile Val Leu
1 5 10 15
Pro Trp Val Thr Ser Gly His Met Ile Pro Met Val Asp Ala Ala Arg
20 25 30
Leu Phe Ala Met His Gly Ala Asp Val Thr Ile Ile Thr Thr Pro Ala
35 40 45
Asn Ala Leu Thr Phe Gln Lys Ser Val Asp Arg Asp Phe Asn Ser Gly
50 55 60
Arg Leu Ile Arg Thr His Thr Leu Lys Phe Pro Ala Ala Glu Val Gly
65 70 75 80
Val Pro Glu Gly Val Glu Asn Phe Asn Asn Thr Ser Pro Glu Met Thr
85 90 95
Ser Lys Val Tyr Leu Gly Val Ser Met Leu Arg Glu Pro Thr Gln Gln
100 105 110
Leu Ile Glu Asp Leu Arg Pro Asp Cys Leu Ile Thr Asp Met Phe Tyr
115 120 125
Pro Trp Ala Val Asp Val Ala Asp Lys Leu Gly Ile Pro Arg Leu Ile
130 135 140
Phe Gln Gly Pro Gly Ser Phe Gly Leu Ser Ala Met His Ser Ile Lys
145 150 155 160
Gln Tyr Glu Pro Phe Lys Ser Val Thr Ser Asp Thr Glu Thr Phe Pro
165 170 175
Leu Pro Gly Leu Pro His Lys Val Glu Met Thr Arg Leu Gln Ile Pro
180 185 190
Lys Trp Val Arg Glu Pro Asn Gly Tyr Thr Gln Leu Met Gly Arg Val
195 200 205
Lys Asp Ser Glu Arg Arg Ser Tyr Gly Ser Leu Val Asn Ser Phe Tyr
210 215 220
Asp Phe Glu Gly Pro Tyr Glu Glu His Tyr Arg Lys Ala Thr Gly Gln
225 230 235 240
Arg Val Trp Ser Ile Gly Pro Val Ser Val Trp Val Asn Gln Asp Ala
245 250 255
Ala Asp Lys Val Gly Arg Gly Gln Asp Leu Val Ala Glu Asp Gln Asn
260 265 270
Ser Trp Leu Asn Trp Leu Asn Ser Lys Glu Lys Asn Ser Val Leu Tyr
275 280 285
Val Ser Phe Gly Ser Met Ala Lys Phe Pro Ser Ala Gln Leu Leu Glu
290 295 300
Ile Ala His Gly Leu Glu Ala Ser Gly His Ser Phe Ile Trp Val Val
305 310 315 320
Arg Lys Val Asp Gly Asp Asp Asp Val Asp Val Trp Leu Pro Asp Phe
325 330 335
Glu Lys Lys Met Lys Glu Asn Asn Lys Gly Phe Ile Ile Arg Asn Trp
340 345 350
Ala Pro Gln Leu Leu Ile Leu Asp His Pro Ala Ile Gly Gly Leu Leu
355 360 365
Asn His Ser Gly Trp Asn Ser Val Leu Glu Gly Ala Thr Ala Gly Leu
370 375 380
Pro Met Ile Thr Trp Pro Leu Tyr Ala Glu His Phe Tyr Asn Glu Arg
385 390 395 400
Leu Val Leu Asp Val Leu Lys Ile Gly Val Pro Val Gly Val Lys Glu
405 410 415
Trp Lys Asn Leu His Glu Val Gly Glu Leu Val Arg Arg Asp Ala Ile
420 425 430
Ala Lys Ala Ile Lys Leu Leu Met Gly Ser Gly Glu Glu Ala Glu Val
435 440 445
Met Arg Lys Lys Ala Lys Glu Leu Gly Val Gly Ala Lys Lys Gly Ile
450 455 460
Gln Val Gly Gly Ser Ser His Thr Asn Leu Ile Ala Val Ile Asp Glu
465 470 475 480
Leu Lys Ser Leu Lys Lys Ser Arg Ile Gln Gly Val
485 490
<210> 31
<211> 1515
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 32的酶的核苷酸
<400> 31
atggtctccg gcgacgacga tgtttctcgt cggccactga aagtttactt cattgcacac 60
ccctcacctg gccatattgc ccctctgacc aaaatagccc atctcttcgc tgccctcggt 120
gagcacgtga ctattctcac tactcccgcc aatgtccact tccatgagaa atccatcgac 180
aaaggaaagg cttccggcta tcatgttaac atccacaccg ttaaatttcc ttctaaagag 240
gtcggtctcc ctgacggcat cgaaaacttc tcttacgcct ccgatgttga aacagcagct 300
aaaatttggg ctggattcgc catgctacaa actgaaatgg agcaatatat ggagcttaac 360
ccacccgatt gcatcgttgc cgacatgttc acctcctgga cctccgactt tgctatcaaa 420
ttgggaatca caagaatcgt tttcaacgtc tattgtattt tcacacgctg tttggaagaa 480
gccatccgat caccggactc gccacacttg aacaaagaaa tctctgataa tgaaccgttt 540
gttatcccgg gtctaccaga ccccataaca attacccgag ctcaactgcc cgacggtacc 600
ttttctccca tgaaagaact agctagaaca gctgagttga agagctttgg aatggtgatc 660
aacgggtttt ccgaactcga aaccgattac atcgagcatt acaagaaaat catgggtcac 720
aaacggattt ggcatgtcgg accccttcag ctaatccacc gtaacgatga agacaaaatt 780
cagaggagcc acaagacagc ggtgctgagt gataacgata acgagttagt gagttggctt 840
aactcgaaga aacccgactc agttatttac atttgcttcg gtagtgcaac tcgtttctct 900
aatcaccagc tctatgaaat cgcctgtgga ttagaagctt ccgggcaccc atttttgtgg 960
ggcctacttt gggtgccaga agatgaagat aacgatgacg tgggcaacaa atggttgcca 1020
gctttcgaag aaagaattaa aaaggaaaat aagggaatga ttttaagggg gtgggctcca 1080
cagatgttaa tcttaaacca cccggcgatc ggtggtttca tgacgcattg tggttggaat 1140
gcggtggtgg aagcactttc attcggtgtt ccgactatta cgcttccagt tttctcggag 1200
cagttttata ctgagagact gatatcacaa gtgctcaaga ctggtgtgga ggttggtgca 1260
gagaagtgga cctatgcatt tgatgcgggg aaatatccgg tgagtaggga aaagatagcg 1320
acggcggtga agaagatatt agacgatgga gaagaggcag aaggaatgag aaagcgggcc 1380
agggagatga aagaaaaagc ccaaaaaagt gttgaagaag gtggatcctc ttataataat 1440
ttaacggcta tgattgaaga tcttaaagaa tttagggcta acaatggcaa ggctgcacaa 1500
gatcatgaat cgtga 1515
<210> 32
<211> 504
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 参与从QA-Di制备QA-TriR或QA-TriX的酶（Qs-3-O-RhaT/XylT）
<400> 32
Met Val Ser Gly Asp Asp Asp Val Ser Arg Arg Pro Leu Lys Val Tyr
1 5 10 15
Phe Ile Ala His Pro Ser Pro Gly His Ile Ala Pro Leu Thr Lys Ile
20 25 30
Ala His Leu Phe Ala Ala Leu Gly Glu His Val Thr Ile Leu Thr Thr
35 40 45
Pro Ala Asn Val His Phe His Glu Lys Ser Ile Asp Lys Gly Lys Ala
50 55 60
Ser Gly Tyr His Val Asn Ile His Thr Val Lys Phe Pro Ser Lys Glu
65 70 75 80
Val Gly Leu Pro Asp Gly Ile Glu Asn Phe Ser Tyr Ala Ser Asp Val
85 90 95
Glu Thr Ala Ala Lys Ile Trp Ala Gly Phe Ala Met Leu Gln Thr Glu
100 105 110
Met Glu Gln Tyr Met Glu Leu Asn Pro Pro Asp Cys Ile Val Ala Asp
115 120 125
Met Phe Thr Ser Trp Thr Ser Asp Phe Ala Ile Lys Leu Gly Ile Thr
130 135 140
Arg Ile Val Phe Asn Val Tyr Cys Ile Phe Thr Arg Cys Leu Glu Glu
145 150 155 160
Ala Ile Arg Ser Pro Asp Ser Pro His Leu Asn Lys Glu Ile Ser Asp
165 170 175
Asn Glu Pro Phe Val Ile Pro Gly Leu Pro Asp Pro Ile Thr Ile Thr
180 185 190
Arg Ala Gln Leu Pro Asp Gly Thr Phe Ser Pro Met Lys Glu Leu Ala
195 200 205
Arg Thr Ala Glu Leu Lys Ser Phe Gly Met Val Ile Asn Gly Phe Ser
210 215 220
Glu Leu Glu Thr Asp Tyr Ile Glu His Tyr Lys Lys Ile Met Gly His
225 230 235 240
Lys Arg Ile Trp His Val Gly Pro Leu Gln Leu Ile His Arg Asn Asp
245 250 255
Glu Asp Lys Ile Gln Arg Ser His Lys Thr Ala Val Leu Ser Asp Asn
260 265 270
Asp Asn Glu Leu Val Ser Trp Leu Asn Ser Lys Lys Pro Asp Ser Val
275 280 285
Ile Tyr Ile Cys Phe Gly Ser Ala Thr Arg Phe Ser Asn His Gln Leu
290 295 300
Tyr Glu Ile Ala Cys Gly Leu Glu Ala Ser Gly His Pro Phe Leu Trp
305 310 315 320
Gly Leu Leu Trp Val Pro Glu Asp Glu Asp Asn Asp Asp Val Gly Asn
325 330 335
Lys Trp Leu Pro Ala Phe Glu Glu Arg Ile Lys Lys Glu Asn Lys Gly
340 345 350
Met Ile Leu Arg Gly Trp Ala Pro Gln Met Leu Ile Leu Asn His Pro
355 360 365
Ala Ile Gly Gly Phe Met Thr His Cys Gly Trp Asn Ala Val Val Glu
370 375 380
Ala Leu Ser Phe Gly Val Pro Thr Ile Thr Leu Pro Val Phe Ser Glu
385 390 395 400
Gln Phe Tyr Thr Glu Arg Leu Ile Ser Gln Val Leu Lys Thr Gly Val
405 410 415
Glu Val Gly Ala Glu Lys Trp Thr Tyr Ala Phe Asp Ala Gly Lys Tyr
420 425 430
Pro Val Ser Arg Glu Lys Ile Ala Thr Ala Val Lys Lys Ile Leu Asp
435 440 445
Asp Gly Glu Glu Ala Glu Gly Met Arg Lys Arg Ala Arg Glu Met Lys
450 455 460
Glu Lys Ala Gln Lys Ser Val Glu Glu Gly Gly Ser Ser Tyr Asn Asn
465 470 475 480
Leu Thr Ala Met Ile Glu Asp Leu Lys Glu Phe Arg Ala Asn Asn Gly
485 490 495
Lys Ala Ala Gln Asp His Glu Ser
500
<210> 33
<211> 1485
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 34的酶的核苷酸
<400> 33
atggtctccg gcgacgacga cgtttctcgt cggccactga aagtttactt tattgcacac 60
ccctcacctg gccatattgc ccctctaacc aaaatagccc aactctttgc tgcacgtggt 120
gagcacgtga ctattcttac tactcccgcc aatgtccact tccatgagaa atccatcgac 180
aaaggaaaga cttccggcta tcatgttaac atccacgccg ttaaatttcc ttctaaagag 240
gtcggtctcc ccgacggcat cgaaaacttc tctcacgcct ccgataatga aacagcagcc 300
aaaatttggg ccggattctc catgcttcaa actgaaatgg agcaatatat ggaacaaaac 360
ccacccgatt gcattgttgc cgacatgttc aaccgctgga cttccgactt cgctatcaaa 420
ttgggaatcc cgagaatagt tttcaacgtc tactgtattt tcacacgctg tttggaagaa 480
gcaatcagat cacctgactc gccacacttg aaactaaact ccgataatga acagtttatt 540
attccgggtc tacccgaccc cataacaatt acccgagctc aactgcccga cggtgccttt 600
tctgtcgtca aagaacaagt tagtgaagct gagttgaaaa gcttcggaat ggtgatcaac 660
gggttttccg aactcgaaac cgaatacatc gagtattaca agaatatcat gggtcgaaaa 720
cggatttggc atgtcggacc ccttcagctc atttaccaaa acgatgaccc caaagttcag 780
aggagccaga agacagcggt cgtgagtgac aacgagttag tgagttggct tgactcgaag 840
aaacccgact cagtgattta catttccttc ggtagtgcaa ttcgtttctc taataagcag 900
ctctatgaaa tagcatgtgg attagaagct tccggctacc catttttgtg ggccttactt 960
tgggtgccag aagatgacga cgacgtgggc aacaaatggt tgcctgattt cgaagaaaga 1020
ataaaaagag aaaataaggg aataattttc agggggtggg ccccacagat gttaatctta 1080
aaccacccgg cgatcggtgg tttcatgacg cattgtggtt ggaatgcggt ggtggaagcg 1140
ctttctttcg gtgttccgac tattacgctt ccggttttct cggagcagtt ttatactgag 1200
agactgatat cacaagtgct caagactggt gtcgaggtcg gtgcagagaa gtggacctat 1260
gcatttgatg cggggaaata tccggtgagt cgggaaaaga tagcgacggc ggtgaagaag 1320
atattagact gtggagaaga ggcagaagga atgagaaagc gggccaggga gatgaaagaa 1380
aaagcccaaa aaagtgttga agaaggtggg tcctcttata ataatttaac ggctatgatt 1440
gaagatctta aagaatttag ggctaacaat ggcaaggttg catga 1485
<210> 34
<211> 494
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 参与从QA-Di制备QA-TriR的酶（Qs_0283850）
<400> 34
Met Val Ser Gly Asp Asp Asp Val Ser Arg Arg Pro Leu Lys Val Tyr
1 5 10 15
Phe Ile Ala His Pro Ser Pro Gly His Ile Ala Pro Leu Thr Lys Ile
20 25 30
Ala Gln Leu Phe Ala Ala Arg Gly Glu His Val Thr Ile Leu Thr Thr
35 40 45
Pro Ala Asn Val His Phe His Glu Lys Ser Ile Asp Lys Gly Lys Thr
50 55 60
Ser Gly Tyr His Val Asn Ile His Ala Val Lys Phe Pro Ser Lys Glu
65 70 75 80
Val Gly Leu Pro Asp Gly Ile Glu Asn Phe Ser His Ala Ser Asp Asn
85 90 95
Glu Thr Ala Ala Lys Ile Trp Ala Gly Phe Ser Met Leu Gln Thr Glu
100 105 110
Met Glu Gln Tyr Met Glu Gln Asn Pro Pro Asp Cys Ile Val Ala Asp
115 120 125
Met Phe Asn Arg Trp Thr Ser Asp Phe Ala Ile Lys Leu Gly Ile Pro
130 135 140
Arg Ile Val Phe Asn Val Tyr Cys Ile Phe Thr Arg Cys Leu Glu Glu
145 150 155 160
Ala Ile Arg Ser Pro Asp Ser Pro His Leu Lys Leu Asn Ser Asp Asn
165 170 175
Glu Gln Phe Ile Ile Pro Gly Leu Pro Asp Pro Ile Thr Ile Thr Arg
180 185 190
Ala Gln Leu Pro Asp Gly Ala Phe Ser Val Val Lys Glu Gln Val Ser
195 200 205
Glu Ala Glu Leu Lys Ser Phe Gly Met Val Ile Asn Gly Phe Ser Glu
210 215 220
Leu Glu Thr Glu Tyr Ile Glu Tyr Tyr Lys Asn Ile Met Gly Arg Lys
225 230 235 240
Arg Ile Trp His Val Gly Pro Leu Gln Leu Ile Tyr Gln Asn Asp Asp
245 250 255
Pro Lys Val Gln Arg Ser Gln Lys Thr Ala Val Val Ser Asp Asn Glu
260 265 270
Leu Val Ser Trp Leu Asp Ser Lys Lys Pro Asp Ser Val Ile Tyr Ile
275 280 285
Ser Phe Gly Ser Ala Ile Arg Phe Ser Asn Lys Gln Leu Tyr Glu Ile
290 295 300
Ala Cys Gly Leu Glu Ala Ser Gly Tyr Pro Phe Leu Trp Ala Leu Leu
305 310 315 320
Trp Val Pro Glu Asp Asp Asp Asp Val Gly Asn Lys Trp Leu Pro Asp
325 330 335
Phe Glu Glu Arg Ile Lys Arg Glu Asn Lys Gly Ile Ile Phe Arg Gly
340 345 350
Trp Ala Pro Gln Met Leu Ile Leu Asn His Pro Ala Ile Gly Gly Phe
355 360 365
Met Thr His Cys Gly Trp Asn Ala Val Val Glu Ala Leu Ser Phe Gly
370 375 380
Val Pro Thr Ile Thr Leu Pro Val Phe Ser Glu Gln Phe Tyr Thr Glu
385 390 395 400
Arg Leu Ile Ser Gln Val Leu Lys Thr Gly Val Glu Val Gly Ala Glu
405 410 415
Lys Trp Thr Tyr Ala Phe Asp Ala Gly Lys Tyr Pro Val Ser Arg Glu
420 425 430
Lys Ile Ala Thr Ala Val Lys Lys Ile Leu Asp Cys Gly Glu Glu Ala
435 440 445
Glu Gly Met Arg Lys Arg Ala Arg Glu Met Lys Glu Lys Ala Gln Lys
450 455 460
Ser Val Glu Glu Gly Gly Ser Ser Tyr Asn Asn Leu Thr Ala Met Ile
465 470 475 480
Glu Asp Leu Lys Glu Phe Arg Ala Asn Asn Gly Lys Val Ala
485 490
<210> 35
<211> 1491
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 36的酶的核苷酸
<400> 35
atggtctccg gcgacgatac cgtttcacgg ccactgatag tttactttat tgcacacccc 60
tcacctggcc atattgcccc tctaaccaaa atagcccaac tcttcgctgc acgtggtgag 120
cacgtcacta ttcttactac tcccgccaat gtccacttcc atgagaaatc catcgacaaa 180
agaaagaatt ccggctatca tgttaacatc cacaccgtta aatttccttc taaagaggtc 240
ggtctccctg acggcatcga aaacttctct cacgcctccg ataatgaaac agcagccaaa 300
atttgggccg gattctccat gcttcaaact gaaatggagc aatatatgga acaaaaccca 360
cccgattgca tcgttgccga catgttcaac cgctggactt ccgacttcgc tatcaaattg 420
ggaatcccga gaatagtttt caacgtctac tgtattttca cacgctgttt ggaagaagca 480
atcagatcac ctgactcgcc acacttgaaa ctaaactccg ataatgaaca gtttattatt 540
cccggtctac ccgaccccat aacaattacc cgagctcaac tccccgacgg tgccttttct 600
gtcgtcaaag aacaagttag tgaagctgag ttgaaaagct tcggaatggt gatcaacggg 660
ttttccgaac tcgaaactga atacatcgag tattacaaga atatcatggg tcgcaaacgg 720
atttggcatg tcggacccct tcagctaatt taccaaaacg acgaccccaa agttcagagg 780
agccagaaga cagcggtctt gagtgacaac gagttagtga gttggcttga ctcgaagaaa 840
cccgactcag tgatttacat ttccttcggt agtgcaattc gtttctctaa taagcagctc 900
tatgaaatcg catgtggatt agaagcttcc ggctacccat ttttgtgggc cttactttgg 960
gtgccagaag atgatgacga cgtgggcaac aaatggttgc cgggtttcga agaaagaata 1020
aaaagagaaa ataagggaat aattttcagg gggtgggccc cacagatgtt aatcttaaac 1080
cacccggcga tcggtggttt catgacgcat tgtggttgga atgcggtggt ggaagcactt 1140
tcattcggtg ttccgactat tacgcttcca gttttctcgg agcagtttta tactgagaga 1200
ctgatatcac aagtgctcaa gactggtgtg gaggttggtg cagagaagtg gacctatgca 1260
tttgatgcgg ggaaatatcc ggtgagtagg gaaaagatag cgacggcggt gaagaagata 1320
ttagacgatg gagaagaggc agaaggaatg agaaagcggg ccagggagat gaaagaaaaa 1380
gcccaaaaaa gtgttgaaga aggtggatcc tcttataata atttaacggc tatgattgaa 1440
gatcttaaag aatttagggc taacaatggc aaggctgcaa tgaaatcatg a 1491
<210> 36
<211> 496
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 参与从QA-Di制备QA-TriR的酶（DN20529_c0_g2_i8）
<400> 36
Met Val Ser Gly Asp Asp Thr Val Ser Arg Pro Leu Ile Val Tyr Phe
1 5 10 15
Ile Ala His Pro Ser Pro Gly His Ile Ala Pro Leu Thr Lys Ile Ala
20 25 30
Gln Leu Phe Ala Ala Arg Gly Glu His Val Thr Ile Leu Thr Thr Pro
35 40 45
Ala Asn Val His Phe His Glu Lys Ser Ile Asp Lys Arg Lys Asn Ser
50 55 60
Gly Tyr His Val Asn Ile His Thr Val Lys Phe Pro Ser Lys Glu Val
65 70 75 80
Gly Leu Pro Asp Gly Ile Glu Asn Phe Ser His Ala Ser Asp Asn Glu
85 90 95
Thr Ala Ala Lys Ile Trp Ala Gly Phe Ser Met Leu Gln Thr Glu Met
100 105 110
Glu Gln Tyr Met Glu Gln Asn Pro Pro Asp Cys Ile Val Ala Asp Met
115 120 125
Phe Asn Arg Trp Thr Ser Asp Phe Ala Ile Lys Leu Gly Ile Pro Arg
130 135 140
Ile Val Phe Asn Val Tyr Cys Ile Phe Thr Arg Cys Leu Glu Glu Ala
145 150 155 160
Ile Arg Ser Pro Asp Ser Pro His Leu Lys Leu Asn Ser Asp Asn Glu
165 170 175
Gln Phe Ile Ile Pro Gly Leu Pro Asp Pro Ile Thr Ile Thr Arg Ala
180 185 190
Gln Leu Pro Asp Gly Ala Phe Ser Val Val Lys Glu Gln Val Ser Glu
195 200 205
Ala Glu Leu Lys Ser Phe Gly Met Val Ile Asn Gly Phe Ser Glu Leu
210 215 220
Glu Thr Glu Tyr Ile Glu Tyr Tyr Lys Asn Ile Met Gly Arg Lys Arg
225 230 235 240
Ile Trp His Val Gly Pro Leu Gln Leu Ile Tyr Gln Asn Asp Asp Pro
245 250 255
Lys Val Gln Arg Ser Gln Lys Thr Ala Val Leu Ser Asp Asn Glu Leu
260 265 270
Val Ser Trp Leu Asp Ser Lys Lys Pro Asp Ser Val Ile Tyr Ile Ser
275 280 285
Phe Gly Ser Ala Ile Arg Phe Ser Asn Lys Gln Leu Tyr Glu Ile Ala
290 295 300
Cys Gly Leu Glu Ala Ser Gly Tyr Pro Phe Leu Trp Ala Leu Leu Trp
305 310 315 320
Val Pro Glu Asp Asp Asp Asp Val Gly Asn Lys Trp Leu Pro Gly Phe
325 330 335
Glu Glu Arg Ile Lys Arg Glu Asn Lys Gly Ile Ile Phe Arg Gly Trp
340 345 350
Ala Pro Gln Met Leu Ile Leu Asn His Pro Ala Ile Gly Gly Phe Met
355 360 365
Thr His Cys Gly Trp Asn Ala Val Val Glu Ala Leu Ser Phe Gly Val
370 375 380
Pro Thr Ile Thr Leu Pro Val Phe Ser Glu Gln Phe Tyr Thr Glu Arg
385 390 395 400
Leu Ile Ser Gln Val Leu Lys Thr Gly Val Glu Val Gly Ala Glu Lys
405 410 415
Trp Thr Tyr Ala Phe Asp Ala Gly Lys Tyr Pro Val Ser Arg Glu Lys
420 425 430
Ile Ala Thr Ala Val Lys Lys Ile Leu Asp Asp Gly Glu Glu Ala Glu
435 440 445
Gly Met Arg Lys Arg Ala Arg Glu Met Lys Glu Lys Ala Gln Lys Ser
450 455 460
Val Glu Glu Gly Gly Ser Ser Tyr Asn Asn Leu Thr Ala Met Ile Glu
465 470 475 480
Asp Leu Lys Glu Phe Arg Ala Asn Asn Gly Lys Ala Ala Met Lys Ser
485 490 495
<210> 37
<211> 1515
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 38的酶的核苷酸
<400> 37
atggtctccg gcgacgacga tgtttctcgt cggccactga aagtttactt cattgcacac 60
ccctcacctg gccatattgc ccctctgacc aaaatagccc atctcttcgc tgccctcggt 120
gagcacgtga ctattctcac tactcccgcc aatgtccact tccatgagaa atccatcgac 180
aaaggaaagg cttccggcta tcatgttaac atccacaccg ttaaatttcc ttctaaagag 240
gtcggtctcc ctgacggcat cgaaaacttc tcttacgcct ccgatgttga aacagcagct 300
aaaatttggg ctggattcgc catgctacaa actgaaatgg agcaatatat ggagcttaac 360
ccacccgatt gcatcgttgc cgacatgttc acctcctgga cctccgactt tgctatcaaa 420
ttgggaatca caagaatcgt tttcaacgtc tattgtattt tcacacgctg tttggaagaa 480
gccatccgat caccggactc gccacacttg aacaaagaaa tctctgataa tgaaccgttt 540
gttatcccgg gtctaccaga ccccataaca attacccgag ctcaactgcc cgacggtacc 600
ttttctccca tgaaagaact agctagaaca gctgagttga agagctttgg aatggtgatc 660
aacgggtttt ccgaactcga aaccgattac atcgagcatt acaagaaaat catgggtcac 720
aaacggattt ggcatgtcgg accccttcag ctaatccacc gtaacgatga agacaaaatt 780
cagaggagcc acaagacagc ggtgctgagt gataacgata acgagttagt gagttggctt 840
aactcgaaga aacccgactc agttatttac atttgcttcg gtagtgcaac tcgtttctct 900
aatcaccagc tctatgaaat cgcctgtgga ttagaagctt ccgggcaccc atttttgtgg 960
ggcctacttt gggtgccaga agatgaagat aacgatgacg tgggcaacaa atggttgcca 1020
gctttcgaag aaagaattaa aaaggaaaat aagggaatga ttttaagggg gtgggctcca 1080
cagatgttaa tcttgaatca cccggcgatc ggtggtttca tgacgcattg tggttggaat 1140
gcggcggtgg aggcgctttc ttccggtgtt ccgattatta catttccggt tttctcggat 1200
cagttttata atgaaaggct gatatcacaa gtgcataagt gtggggtggg ggttggtacg 1260
gaggcgtgga gctatgcatt cgatgccggg aagaatccgg tgggtcggga aaagataatg 1320
acggcggtga agaagatatt agacggtgga gaagaggcgg aaggaatgag aaagagggcc 1380
cgggagctga aagaaatagc taaaagaagt gtggaagaag gtgggtcctc ttataataat 1440
ttaacggcta tgattcaaga tctgaaagaa tttagagcta acaatggcaa ggctgcacaa 1500
gatcatgaat cgtga 1515
<210> 38
<211> 504
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 参与从QA-Di制备QA-TriX的酶（Qs_0283870）
<400> 38
Met Val Ser Gly Asp Asp Asp Val Ser Arg Arg Pro Leu Lys Val Tyr
1 5 10 15
Phe Ile Ala His Pro Ser Pro Gly His Ile Ala Pro Leu Thr Lys Ile
20 25 30
Ala His Leu Phe Ala Ala Leu Gly Glu His Val Thr Ile Leu Thr Thr
35 40 45
Pro Ala Asn Val His Phe His Glu Lys Ser Ile Asp Lys Gly Lys Ala
50 55 60
Ser Gly Tyr His Val Asn Ile His Thr Val Lys Phe Pro Ser Lys Glu
65 70 75 80
Val Gly Leu Pro Asp Gly Ile Glu Asn Phe Ser Tyr Ala Ser Asp Val
85 90 95
Glu Thr Ala Ala Lys Ile Trp Ala Gly Phe Ala Met Leu Gln Thr Glu
100 105 110
Met Glu Gln Tyr Met Glu Leu Asn Pro Pro Asp Cys Ile Val Ala Asp
115 120 125
Met Phe Thr Ser Trp Thr Ser Asp Phe Ala Ile Lys Leu Gly Ile Thr
130 135 140
Arg Ile Val Phe Asn Val Tyr Cys Ile Phe Thr Arg Cys Leu Glu Glu
145 150 155 160
Ala Ile Arg Ser Pro Asp Ser Pro His Leu Asn Lys Glu Ile Ser Asp
165 170 175
Asn Glu Pro Phe Val Ile Pro Gly Leu Pro Asp Pro Ile Thr Ile Thr
180 185 190
Arg Ala Gln Leu Pro Asp Gly Thr Phe Ser Pro Met Lys Glu Leu Ala
195 200 205
Arg Thr Ala Glu Leu Lys Ser Phe Gly Met Val Ile Asn Gly Phe Ser
210 215 220
Glu Leu Glu Thr Asp Tyr Ile Glu His Tyr Lys Lys Ile Met Gly His
225 230 235 240
Lys Arg Ile Trp His Val Gly Pro Leu Gln Leu Ile His Arg Asn Asp
245 250 255
Glu Asp Lys Ile Gln Arg Ser His Lys Thr Ala Val Leu Ser Asp Asn
260 265 270
Asp Asn Glu Leu Val Ser Trp Leu Asn Ser Lys Lys Pro Asp Ser Val
275 280 285
Ile Tyr Ile Cys Phe Gly Ser Ala Thr Arg Phe Ser Asn His Gln Leu
290 295 300
Tyr Glu Ile Ala Cys Gly Leu Glu Ala Ser Gly His Pro Phe Leu Trp
305 310 315 320
Gly Leu Leu Trp Val Pro Glu Asp Glu Asp Asn Asp Asp Val Gly Asn
325 330 335
Lys Trp Leu Pro Ala Phe Glu Glu Arg Ile Lys Lys Glu Asn Lys Gly
340 345 350
Met Ile Leu Arg Gly Trp Ala Pro Gln Met Leu Ile Leu Asn His Pro
355 360 365
Ala Ile Gly Gly Phe Met Thr His Cys Gly Trp Asn Ala Ala Val Glu
370 375 380
Ala Leu Ser Ser Gly Val Pro Ile Ile Thr Phe Pro Val Phe Ser Asp
385 390 395 400
Gln Phe Tyr Asn Glu Arg Leu Ile Ser Gln Val His Lys Cys Gly Val
405 410 415
Gly Val Gly Thr Glu Ala Trp Ser Tyr Ala Phe Asp Ala Gly Lys Asn
420 425 430
Pro Val Gly Arg Glu Lys Ile Met Thr Ala Val Lys Lys Ile Leu Asp
435 440 445
Gly Gly Glu Glu Ala Glu Gly Met Arg Lys Arg Ala Arg Glu Leu Lys
450 455 460
Glu Ile Ala Lys Arg Ser Val Glu Glu Gly Gly Ser Ser Tyr Asn Asn
465 470 475 480
Leu Thr Ala Met Ile Gln Asp Leu Lys Glu Phe Arg Ala Asn Asn Gly
485 490 495
Lys Ala Ala Gln Asp His Glu Ser
500
<210> 39
<211> 1053
<212> DNA
<213> 人工序列
<220>
<223> 刺胞虫小球藻病毒1 UDP-d-葡萄糖4,6-脱水酶（ATCV-1）编码序列（1053bp）：NB：该序列对于在本氏烟草中的表达进行了密码子优化。可以作为Genbank ID：NC_008724.1查找原始序列
<400> 39
atgaatagtc aggagtatac tcctaaatca gtccttgtaa ctggtggggc aggtttcatt 60
ggcagccatg tcgtgatgaa attggtccag aggtatccgg aatgcaaggt cgttgttctt 120
gacaaaatgg attactgcgc taccttaaat aatcttgcta cggtacgaga tgcccccaat 180
tttaaatttg taaaaggtga tatacaaagc actgatcttt tagctcacgt gctcaaacag 240
gaaaagatag ataccattat gcactttgcc gcccagaccc atgtagataa tagctttggc 300
aatagtttag catttacgat gaacaacgta tacggcactc acgtccttct cgaatgtgcc 360
cgattgtatg gtggtgttca gagattcatt aacgtgtcaa ctgatgaggt ctacggtgag 420
agttccttgg gaaagaagga ggggttggac gaacactcct ccctcgaacc gacaaatcct 480
tatgccgccg caaaggctgg agctgaaatg atggctagag catatcatac gtcatacaaa 540
ctcccggtaa tagtcacgcg tggcaataat gtatatggtc cgcaccagtt ccccgaaaaa 600
atgatcccca aatttattct cagggcaacc agaggcctcg atttgccaat acatggtgat 660
ggcggcgccc tgcgatcata cctttacgtc gatgatgttg ccgaagctta tattacaatt 720
cttttaaagg gcaatgttgg agagacctat aacatcggca cgcaaaagga gcgatccgtt 780
gtggacgtgg cccatgacat ctgcaagatt tttaaccgag actcagatac agctatatgg 840
cacgttaaag accgagcctt caatgatcga cgttatttta tttctgataa aaaattactt 900
gacctcggct ggcaagaaaa aaccacctgg gaggacggtc ttaagcaaac tgtagggtgg 960
tatttgcaac atgcaactag gtcctactgg gatcacggca acatggaatt agctttagac 1020
gcccatccga cacttcaagt tcctaaattc taa 1053
<210> 40
<211> 350
<212> PRT
<213> 人工序列
<220>
<223> 刺胞虫小球藻病毒1 UDP-d-葡萄糖4,6-脱水酶（ATCV-1）转化的核苷酸序列（350aa）
<400> 40
Met Asn Ser Gln Glu Tyr Thr Pro Lys Ser Val Leu Val Thr Gly Gly
1 5 10 15
Ala Gly Phe Ile Gly Ser His Val Val Met Lys Leu Val Gln Arg Tyr
20 25 30
Pro Glu Cys Lys Val Val Val Leu Asp Lys Met Asp Tyr Cys Ala Thr
35 40 45
Leu Asn Asn Leu Ala Thr Val Arg Asp Ala Pro Asn Phe Lys Phe Val
50 55 60
Lys Gly Asp Ile Gln Ser Thr Asp Leu Leu Ala His Val Leu Lys Gln
65 70 75 80
Glu Lys Ile Asp Thr Ile Met His Phe Ala Ala Gln Thr His Val Asp
85 90 95
Asn Ser Phe Gly Asn Ser Leu Ala Phe Thr Met Asn Asn Val Tyr Gly
100 105 110
Thr His Val Leu Leu Glu Cys Ala Arg Leu Tyr Gly Gly Val Gln Arg
115 120 125
Phe Ile Asn Val Ser Thr Asp Glu Val Tyr Gly Glu Ser Ser Leu Gly
130 135 140
Lys Lys Glu Gly Leu Asp Glu His Ser Ser Leu Glu Pro Thr Asn Pro
145 150 155 160
Tyr Ala Ala Ala Lys Ala Gly Ala Glu Met Met Ala Arg Ala Tyr His
165 170 175
Thr Ser Tyr Lys Leu Pro Val Ile Val Thr Arg Gly Asn Asn Val Tyr
180 185 190
Gly Pro His Gln Phe Pro Glu Lys Met Ile Pro Lys Phe Ile Leu Arg
195 200 205
Ala Thr Arg Gly Leu Asp Leu Pro Ile His Gly Asp Gly Gly Ala Leu
210 215 220
Arg Ser Tyr Leu Tyr Val Asp Asp Val Ala Glu Ala Tyr Ile Thr Ile
225 230 235 240
Leu Leu Lys Gly Asn Val Gly Glu Thr Tyr Asn Ile Gly Thr Gln Lys
245 250 255
Glu Arg Ser Val Val Asp Val Ala His Asp Ile Cys Lys Ile Phe Asn
260 265 270
Arg Asp Ser Asp Thr Ala Ile Trp His Val Lys Asp Arg Ala Phe Asn
275 280 285
Asp Arg Arg Tyr Phe Ile Ser Asp Lys Lys Leu Leu Asp Leu Gly Trp
290 295 300
Gln Glu Lys Thr Thr Trp Glu Asp Gly Leu Lys Gln Thr Val Gly Trp
305 310 315 320
Tyr Leu Gln His Ala Thr Arg Ser Tyr Trp Asp His Gly Asn Met Glu
325 330 335
Leu Ala Leu Asp Ala His Pro Thr Leu Gln Val Pro Lys Phe
340 345 350
<210> 41
<211> 693
<212> DNA
<213> 人工序列
<220>
<223> 伴放线放线杆菌NDP-4-酮6-脱氧-葡萄糖4-酮还原酶（AaFCD）编码序列（693bp）：NB：该序列对于在本氏烟草中的表达进行了密码子优化。可以作为Genbank ID：AB002668.1查找原始序列
<400> 41
atgataattg gcaacggtat gctggcaaaa gcctttgaat cattccataa gcgaacttac 60
aattacataa tatttgcatc cggagtgagc aactcaaacg aaacttcctt cgagaatttc 120
aacagagaga aggaattgct tcttgaagtc ctggagcaat ataaagacaa aactatcgtt 180
tactttagtt cctgctccat atacgattct agtttgacga attctttgta tgtctaccac 240
aaaatgtgta tggagagact ggtgcgtgaa aactccaaga attatctcat agcccgtctc 300
ccccaagtta ttggtaaaac gtattcacca accattgtca acttcctttt taacaaaatc 360
aaaaataggg agtgtttcag catattcgga aaagctcacc gaaattttat cgacgtggat 420
gatgtcgtta aggtcaccaa ttacttattg aaggagggtc tgttcattaa cagtattgtg 480
aacttggcaa gcacgcacca tacctccatg tacgaattaa tcttatattt ggaaaaaata 540
agtaatcaac gtgccttcta taatgttgag aacaaagggt ctaggtactt tattgatgtt 600
tcaatactgc aggatgttta tcagaagctg gggatcaaat ttgacaaaga ttacgtagaa 660
aaggttatca acaagtacta cgctattaag taa 693
<210> 42
<211> 230
<212> PRT
<213> 人工序列
<220>
<223> 伴放线放线杆菌NDP-4-酮6-脱氧-葡萄糖4-酮还原酶（AaFCD）转化的核苷酸序列（230aa）
<400> 42
Met Ile Ile Gly Asn Gly Met Leu Ala Lys Ala Phe Glu Ser Phe His
1 5 10 15
Lys Arg Thr Tyr Asn Tyr Ile Ile Phe Ala Ser Gly Val Ser Asn Ser
20 25 30
Asn Glu Thr Ser Phe Glu Asn Phe Asn Arg Glu Lys Glu Leu Leu Leu
35 40 45
Glu Val Leu Glu Gln Tyr Lys Asp Lys Thr Ile Val Tyr Phe Ser Ser
50 55 60
Cys Ser Ile Tyr Asp Ser Ser Leu Thr Asn Ser Leu Tyr Val Tyr His
65 70 75 80
Lys Met Cys Met Glu Arg Leu Val Arg Glu Asn Ser Lys Asn Tyr Leu
85 90 95
Ile Ala Arg Leu Pro Gln Val Ile Gly Lys Thr Tyr Ser Pro Thr Ile
100 105 110
Val Asn Phe Leu Phe Asn Lys Ile Lys Asn Arg Glu Cys Phe Ser Ile
115 120 125
Phe Gly Lys Ala His Arg Asn Phe Ile Asp Val Asp Asp Val Val Lys
130 135 140
Val Thr Asn Tyr Leu Leu Lys Glu Gly Leu Phe Ile Asn Ser Ile Val
145 150 155 160
Asn Leu Ala Ser Thr His His Thr Ser Met Tyr Glu Leu Ile Leu Tyr
165 170 175
Leu Glu Lys Ile Ser Asn Gln Arg Ala Phe Tyr Asn Val Glu Asn Lys
180 185 190
Gly Ser Arg Tyr Phe Ile Asp Val Ser Ile Leu Gln Asp Val Tyr Gln
195 200 205
Lys Leu Gly Ile Lys Phe Asp Lys Asp Tyr Val Glu Lys Val Ile Asn
210 215 220
Lys Tyr Tyr Ala Ile Lys
225 230
<210> 43
<211> 927
<212> DNA
<213> 人工序列
<220>
<223> 喜温无氧芽孢杆菌（Anoxybacillus tepidamans）NDP-4-酮6-脱氧-葡萄糖4-酮还原酶（AtFCD）编码序列（927bp）：NB：该序列对于在本氏烟草中的表达进行了密码子优化。可以作为Genbank ID：AY883421.5查找原始序列
<400> 43
atgaagagga tactgatact cggatgcggt tacctgggtt taaatctcgc aaactatttt 60
tgtaaaaaaa attatgatgt ctcagtgata gggagaaagt ctgtctatag caattttttg 120
gaagaggaga tagagttcat agaagatgat atcaaaaata taaatagtta taagcacatg 180
tttaatgagg agacaaccgt catttacgcc ataggaagta ttaacgcaaa taactatttt 240
atggacctga ggaatgatat agaaaactca tacatcccct tcattaacct ccttaacttt 300
ctttccgaaa agtatattca aaagttcgtc tttctctctt cagccggaac agtctatggg 360
aacgtgaata agaattatat aagcgagaat gagattctta acccaatttc aatctatggt 420
ttgcagaaag ccttctttga acaactgata aggattaaaa acaatgaggc tagccatttc 480
aggtatttga tcttcagaat atctaacccc tatgggggaa tcaacattcc gaacaagaat 540
cagggaatta ttccgacgtt agtgtacaaa gccgtgaaca atgagccttt cgaactttgg 600
gcatcaatca ataccatccg tgattatatt tacatcgatg accttagcga attgatctac 660
aaaacaatct atctggacat ttataacgag accctcaatc tcgggtccgg taaaggaaca 720
tcaatcaagc aactcattag cctcgtggag gagattttgg gaaagaagat cactattctt 780
gaaaagcccc ccataaagac taacgttttg aaaaatatac ttgatatttc taagctcgtc 840
aacaccgtag gctacgaacc aaagatcagc attgaagagg gtattagccg ttacatcaac 900
actattttaa cgaagaacat tttttaa 927
<210> 44
<211> 308
<212> PRT
<213> 人工序列
<220>
<223> 喜温无氧芽孢杆菌（Anoxybacillus tepidamans）NDP-4-酮6-脱氧-葡萄糖4-酮还原酶（AtFCD）转化的核苷酸序列（308aa）
<400> 44
Met Lys Arg Ile Leu Ile Leu Gly Cys Gly Tyr Leu Gly Leu Asn Leu
1 5 10 15
Ala Asn Tyr Phe Cys Lys Lys Asn Tyr Asp Val Ser Val Ile Gly Arg
20 25 30
Lys Ser Val Tyr Ser Asn Phe Leu Glu Glu Glu Ile Glu Phe Ile Glu
35 40 45
Asp Asp Ile Lys Asn Ile Asn Ser Tyr Lys His Met Phe Asn Glu Glu
50 55 60
Thr Thr Val Ile Tyr Ala Ile Gly Ser Ile Asn Ala Asn Asn Tyr Phe
65 70 75 80
Met Asp Leu Arg Asn Asp Ile Glu Asn Ser Tyr Ile Pro Phe Ile Asn
85 90 95
Leu Leu Asn Phe Leu Ser Glu Lys Tyr Ile Gln Lys Phe Val Phe Leu
100 105 110
Ser Ser Ala Gly Thr Val Tyr Gly Asn Val Asn Lys Asn Tyr Ile Ser
115 120 125
Glu Asn Glu Ile Leu Asn Pro Ile Ser Ile Tyr Gly Leu Gln Lys Ala
130 135 140
Phe Phe Glu Gln Leu Ile Arg Ile Lys Asn Asn Glu Ala Ser His Phe
145 150 155 160
Arg Tyr Leu Ile Phe Arg Ile Ser Asn Pro Tyr Gly Gly Ile Asn Ile
165 170 175
Pro Asn Lys Asn Gln Gly Ile Ile Pro Thr Leu Val Tyr Lys Ala Val
180 185 190
Asn Asn Glu Pro Phe Glu Leu Trp Ala Ser Ile Asn Thr Ile Arg Asp
195 200 205
Tyr Ile Tyr Ile Asp Asp Leu Ser Glu Leu Ile Tyr Lys Thr Ile Tyr
210 215 220
Leu Asp Ile Tyr Asn Glu Thr Leu Asn Leu Gly Ser Gly Lys Gly Thr
225 230 235 240
Ser Ile Lys Gln Leu Ile Ser Leu Val Glu Glu Ile Leu Gly Lys Lys
245 250 255
Ile Thr Ile Leu Glu Lys Pro Pro Ile Lys Thr Asn Val Leu Lys Asn
260 265 270
Ile Leu Asp Ile Ser Lys Leu Val Asn Thr Val Gly Tyr Glu Pro Lys
275 280 285
Ile Ser Ile Glu Glu Gly Ile Ser Arg Tyr Ile Asn Thr Ile Leu Thr
290 295 300
Lys Asn Ile Phe
305
<210> 45
<211> 951
<212> DNA
<213> 人工序列
<220>
<223> 大肠杆菌（Escherichia coli）NDP-4-酮6-脱氧-葡萄糖4-酮还原酶（EcFCD）编码序列（951bp）：NB：该序列对于在本氏烟草中的表达进行了密码子优化。可以作为GenbankID：AY528413.1查找原始序列
<400> 45
atggatgctc gtaaaaatgg ggtattaata accggtggag ctgggttcat aggtaaagcc 60
ttaataactg aaatggtcga acgtcaaatt cccctggtgt catttgacat cagcgataag 120
cccgacagtt tgccagagct ttccgaatat ttcaactggt ataaattctc ataccttgag 180
agttcacaga ggattaaaga gcttcacgaa atagtttcca ggcataacat caaaacggtc 240
atccatttag ctacaactat gtttccccac gaatccaaaa agaacatcga taaggattgc 300
ttagaaaacg tttatgccaa cgtgtgtttc tttaagaatt tatatgaaaa cggctgtgaa 360
aaaattatct tcgcctcatc aggtggcacc gtatatggga agtctgatac acccttctcc 420
gaagacgatg ccctgcttcc cgaaatttcc tacggactgt ccaaggttat gactgaaact 480
tatctccgat tcatagccaa ggaattgaat gggaagtcca tctctctcag aatatctaac 540
ccctatggtg aggggcaaag gattgacggg aaacaaggag tcattccaat tttcctcaat 600
aaaatcagca acgacatccc catcgacatc attggctcta tcgaatcaaa gcgagactac 660
atttatattt cagatctcgt acaagctttc atgtgctctc tggaatatga aggtcacgaa 720
gacatattta atataggttc tggggaaagc ataactctga agaaattgat cgagacgatt 780
gagttcaagc tgaacaagaa ggctgtgatt ggatttcaag atccgatcca caccaatgcc 840
aatggtataa ttctcgacat caaacgagcc atggcagaac tcggctggag gcccaccgtg 900
gtcctggatg atggcatcga taaattaatc aagagcattc gatgcaagta a 951
<210> 46
<211> 316
<212> PRT
<213> 人工序列
<220>
<223> 大肠杆菌（Echerichia coli）NDP-4-酮6-脱氧-葡萄糖4-酮还原酶（EcFCD）转化的核苷酸序列（316aa）
<400> 46
Met Asp Ala Arg Lys Asn Gly Val Leu Ile Thr Gly Gly Ala Gly Phe
1 5 10 15
Ile Gly Lys Ala Leu Ile Thr Glu Met Val Glu Arg Gln Ile Pro Leu
20 25 30
Val Ser Phe Asp Ile Ser Asp Lys Pro Asp Ser Leu Pro Glu Leu Ser
35 40 45
Glu Tyr Phe Asn Trp Tyr Lys Phe Ser Tyr Leu Glu Ser Ser Gln Arg
50 55 60
Ile Lys Glu Leu His Glu Ile Val Ser Arg His Asn Ile Lys Thr Val
65 70 75 80
Ile His Leu Ala Thr Thr Met Phe Pro His Glu Ser Lys Lys Asn Ile
85 90 95
Asp Lys Asp Cys Leu Glu Asn Val Tyr Ala Asn Val Cys Phe Phe Lys
100 105 110
Asn Leu Tyr Glu Asn Gly Cys Glu Lys Ile Ile Phe Ala Ser Ser Gly
115 120 125
Gly Thr Val Tyr Gly Lys Ser Asp Thr Pro Phe Ser Glu Asp Asp Ala
130 135 140
Leu Leu Pro Glu Ile Ser Tyr Gly Leu Ser Lys Val Met Thr Glu Thr
145 150 155 160
Tyr Leu Arg Phe Ile Ala Lys Glu Leu Asn Gly Lys Ser Ile Ser Leu
165 170 175
Arg Ile Ser Asn Pro Tyr Gly Glu Gly Gln Arg Ile Asp Gly Lys Gln
180 185 190
Gly Val Ile Pro Ile Phe Leu Asn Lys Ile Ser Asn Asp Ile Pro Ile
195 200 205
Asp Ile Ile Gly Ser Ile Glu Ser Lys Arg Asp Tyr Ile Tyr Ile Ser
210 215 220
Asp Leu Val Gln Ala Phe Met Cys Ser Leu Glu Tyr Glu Gly His Glu
225 230 235 240
Asp Ile Phe Asn Ile Gly Ser Gly Glu Ser Ile Thr Leu Lys Lys Leu
245 250 255
Ile Glu Thr Ile Glu Phe Lys Leu Asn Lys Lys Ala Val Ile Gly Phe
260 265 270
Gln Asp Pro Ile His Thr Asn Ala Asn Gly Ile Ile Leu Asp Ile Lys
275 280 285
Arg Ala Met Ala Glu Leu Gly Trp Arg Pro Thr Val Val Leu Asp Asp
290 295 300
Gly Ile Asp Lys Leu Ile Lys Ser Ile Arg Cys Lys
305 310 315
<210> 47
<211> 897
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 48的QsFSL-1酶的核苷酸。QsFSL-1
<400> 47
atggcagaag caacagagag gtatgctgtt gtgacaggat ctaataaagg aattggattt 60
gggatatgca agcagctggc ttctaagggg attacagtag tgctaacagc tagagatgat 120
aagagaggtc ttgaagcagt tgagaaattg aaagaatttg atctgcatgg tcatgtgctt 180
tttcatcaac ttgatgtgtc tgatacagct agtgttacta gccttgcaga ttttatcaaa 240
acccagtttg ggaaactaga tatcttggta aacaatgcag gtataactgg aaccactgta 300
gatgctgatg ctttagcatc ttcaggctat ggtactgggg gtgaacgtaa acctattgat 360
tggaataaaa tagtgataga gacttatgaa tcagttgaaa aagctatcaa caccaactat 420
tatggagcca aaagaatggc tgaagcactt ataccccttc ttcaagtatc agactcacca 480
aggattgtta atgcttcctc tcctatggca aagctagaga atattccaag tggatggggt 540
aaggaagtgc taagtgatgt tgatagccta acagaagaga aacttgatga gatgttgacc 600
caattattga aagatttcaa agagggttca ttagaaacca aaggctggcc tactcttatg 660
tcttcgtata taatctcaaa agctgcttta aatgcctaca caaggattct tgctaagaag 720
tacccatctt tctgcatcaa ttgtgtagac cctggtcatg tgaagactga cataaatcgt 780
cacaccggcc acttaagtat tgatgaaggt gctgaaagcc atgtgagatt ggccctgctg 840
cctgatggtg gcccttctgg acatttcttc tccaggactg aagagacacc attttga 897
<210> 48
<211> 298
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 氧化还原酶，其能够增强岩藻糖基转移酶的活性（QsFSL-1）
<400> 48
Met Ala Glu Ala Thr Glu Arg Tyr Ala Val Val Thr Gly Ser Asn Lys
1 5 10 15
Gly Ile Gly Phe Gly Ile Cys Lys Gln Leu Ala Ser Lys Gly Ile Thr
20 25 30
Val Val Leu Thr Ala Arg Asp Asp Lys Arg Gly Leu Glu Ala Val Glu
35 40 45
Lys Leu Lys Glu Phe Asp Leu His Gly His Val Leu Phe His Gln Leu
50 55 60
Asp Val Ser Asp Thr Ala Ser Val Thr Ser Leu Ala Asp Phe Ile Lys
65 70 75 80
Thr Gln Phe Gly Lys Leu Asp Ile Leu Val Asn Asn Ala Gly Ile Thr
85 90 95
Gly Thr Thr Val Asp Ala Asp Ala Leu Ala Ser Ser Gly Tyr Gly Thr
100 105 110
Gly Gly Glu Arg Lys Pro Ile Asp Trp Asn Lys Ile Val Ile Glu Thr
115 120 125
Tyr Glu Ser Val Glu Lys Ala Ile Asn Thr Asn Tyr Tyr Gly Ala Lys
130 135 140
Arg Met Ala Glu Ala Leu Ile Pro Leu Leu Gln Val Ser Asp Ser Pro
145 150 155 160
Arg Ile Val Asn Ala Ser Ser Pro Met Ala Lys Leu Glu Asn Ile Pro
165 170 175
Ser Gly Trp Gly Lys Glu Val Leu Ser Asp Val Asp Ser Leu Thr Glu
180 185 190
Glu Lys Leu Asp Glu Met Leu Thr Gln Leu Leu Lys Asp Phe Lys Glu
195 200 205
Gly Ser Leu Glu Thr Lys Gly Trp Pro Thr Leu Met Ser Ser Tyr Ile
210 215 220
Ile Ser Lys Ala Ala Leu Asn Ala Tyr Thr Arg Ile Leu Ala Lys Lys
225 230 235 240
Tyr Pro Ser Phe Cys Ile Asn Cys Val Asp Pro Gly His Val Lys Thr
245 250 255
Asp Ile Asn Arg His Thr Gly His Leu Ser Ile Asp Glu Gly Ala Glu
260 265 270
Ser His Val Arg Leu Ala Leu Leu Pro Asp Gly Gly Pro Ser Gly His
275 280 285
Phe Phe Ser Arg Thr Glu Glu Thr Pro Phe
290 295
<210> 49
<211> 915
<212> DNA
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 50的酶的核苷酸。QsFSL-2
<400> 49
atgggttcag atggaaggga tgtagcagag aggtatgcag tggttacagg tgcaaacaaa 60
ggcataggcc tagaaaccgt gcggcaacta gcgtctcacg gcattacagt tgtgttgaca 120
gctcgagatg agaagagagg gactgaagcc acaagaaagc tccaccagct gggtttgtca 180
aatttgattt tccatcagct ggatgtttta gaccctgtta gcattcagtc actggccaag 240
ttcatccaag acaaatttgg caggcttgat atcctggtta ataatgctgg agcatctgga 300
cttgcagctg atgagaaagc tctgaaggca ttaaacatag ataatgcagc ttggctctca 360
ggcaaggccg ccaatttagt tcaaggaatt gtcacacata cctatgagca aggcgaagaa 420
tgcataaata caaactatta tggtgtcaaa agggtgacgg aagctctcct accgctgtta 480
caactttccc ctataggagc aaggataata aatgtttcct cttgcagggg tgagctaaag 540
aggattccaa tgaacgtaag aaatgaactg ggcgacatca aagttctgac tgaaggcaga 600
atagatgcaa ttttgatgaa atttctacac gattttaagg ataatgcact tgagtccaac 660
ggatggacat tgatggggcc tgcttatagc atttcgaagg ccagtctcaa tgcctacact 720
agacttcttg ccaaaaagta ccccgagatg ctcattaact gtgttcatcc tggttatgtc 780
aacacagata tgacttggca tagagggata ctgacggtag aagagggtgc taaaggccca 840
gccatgctag ctcttttgca agatggagga cctacaggtt gctattttga tagtactcaa 900
caggcagaat tttaa 915
<210> 50
<211> 304
<212> PRT
<213> 皂树（Quillaja saponaria）
<220>
<221> misc_feature
<223> 氧化还原酶，其能够增强岩藻糖基转移酶的活性（QsFSL-2）
<400> 50
Met Gly Ser Asp Gly Arg Asp Val Ala Glu Arg Tyr Ala Val Val Thr
1 5 10 15
Gly Ala Asn Lys Gly Ile Gly Leu Glu Thr Val Arg Gln Leu Ala Ser
20 25 30
His Gly Ile Thr Val Val Leu Thr Ala Arg Asp Glu Lys Arg Gly Thr
35 40 45
Glu Ala Thr Arg Lys Leu His Gln Leu Gly Leu Ser Asn Leu Ile Phe
50 55 60
His Gln Leu Asp Val Leu Asp Pro Val Ser Ile Gln Ser Leu Ala Lys
65 70 75 80
Phe Ile Gln Asp Lys Phe Gly Arg Leu Asp Ile Leu Val Asn Asn Ala
85 90 95
Gly Ala Ser Gly Leu Ala Ala Asp Glu Lys Ala Leu Lys Ala Leu Asn
100 105 110
Ile Asp Asn Ala Ala Trp Leu Ser Gly Lys Ala Ala Asn Leu Val Gln
115 120 125
Gly Ile Val Thr His Thr Tyr Glu Gln Gly Glu Glu Cys Ile Asn Thr
130 135 140
Asn Tyr Tyr Gly Val Lys Arg Val Thr Glu Ala Leu Leu Pro Leu Leu
145 150 155 160
Gln Leu Ser Pro Ile Gly Ala Arg Ile Ile Asn Val Ser Ser Cys Arg
165 170 175
Gly Glu Leu Lys Arg Ile Pro Met Asn Val Arg Asn Glu Leu Gly Asp
180 185 190
Ile Lys Val Leu Thr Glu Gly Arg Ile Asp Ala Ile Leu Met Lys Phe
195 200 205
Leu His Asp Phe Lys Asp Asn Ala Leu Glu Ser Asn Gly Trp Thr Leu
210 215 220
Met Gly Pro Ala Tyr Ser Ile Ser Lys Ala Ser Leu Asn Ala Tyr Thr
225 230 235 240
Arg Leu Leu Ala Lys Lys Tyr Pro Glu Met Leu Ile Asn Cys Val His
245 250 255
Pro Gly Tyr Val Asn Thr Asp Met Thr Trp His Arg Gly Ile Leu Thr
260 265 270
Val Glu Glu Gly Ala Lys Gly Pro Ala Met Leu Ala Leu Leu Gln Asp
275 280 285
Gly Gly Pro Thr Gly Cys Tyr Phe Asp Ser Thr Gln Gln Ala Glu Phe
290 295 300
<210> 51
<211> 909
<212> DNA
<213> 鼠尾草（Salvia officinalis）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 52的酶的核苷酸。SoFSL-1
<400> 51
atggctgaag catcctcatt tcttgcacag aaaaggtatg cggtcgtgac aggagcaaac 60
aaaggactag gactagaaat atgcggacag cttgcttcac agggggtgac ggtactgctg 120
acatccagag atgaaaaacg aggcttagaa gccattgagg agcttaagaa atcggggatt 180
aattcggaaa atcttgaata tcatcagctg gatgttacta agccagctag tttcgcttct 240
ctggccgatt tcatcaaggc caaatttggc aagcttgata tcctggtgaa caatgcaggg 300
atcagcggtg ttattgtaga ttatgcagct ttaatggaag ccattcgccg tcgaggggca 360
gagatcaatt acgatggagt gatgaaacag acctacgagc tagcagagga atgcttgcaa 420
acaaattact atggtgtgaa aagaaccatt aatgctctcc ttccgctact tcagttttcc 480
gattcaccaa ggatcgtcaa tgtttcctcc gatgttggcc tccttaagaa aatacccggc 540
gagagaatca gagaagcctt aggcgacgtg gaaaaactta cggaagaaag cgtggacggg 600
attttagacg agtttctaag agatttcaag gaaggcaaga tcgcagagaa aggttggcct 660
acgtttaaga gcgcctattc aatctcaaag gcggcgctca attcgtacac gagggtttta 720
gcacggaaat acccgtcgat catcatcaac tgtgtctgcc cgggtgtcgt caaaaccgat 780
atcaatctta aaatgggcca cttgacggtt gaagaaggcg cggccagtcc cgtgaggtta 840
gcactcatgc cccttggttc gccttccggc ctgttctata ctcgaaacga agtaactcca 900
tttgaatga 909
<210> 52
<211> 302
<212> PRT
<213> 鼠尾草（Salvia officinalis）
<220>
<221> misc_feature
<223> 氧化还原酶，其能够增强岩藻糖基转移酶的活性（SoFSL-1）
<400> 52
Met Ala Glu Ala Ser Ser Phe Leu Ala Gln Lys Arg Tyr Ala Val Val
1 5 10 15
Thr Gly Ala Asn Lys Gly Leu Gly Leu Glu Ile Cys Gly Gln Leu Ala
20 25 30
Ser Gln Gly Val Thr Val Leu Leu Thr Ser Arg Asp Glu Lys Arg Gly
35 40 45
Leu Glu Ala Ile Glu Glu Leu Lys Lys Ser Gly Ile Asn Ser Glu Asn
50 55 60
Leu Glu Tyr His Gln Leu Asp Val Thr Lys Pro Ala Ser Phe Ala Ser
65 70 75 80
Leu Ala Asp Phe Ile Lys Ala Lys Phe Gly Lys Leu Asp Ile Leu Val
85 90 95
Asn Asn Ala Gly Ile Ser Gly Val Ile Val Asp Tyr Ala Ala Leu Met
100 105 110
Glu Ala Ile Arg Arg Arg Gly Ala Glu Ile Asn Tyr Asp Gly Val Met
115 120 125
Lys Gln Thr Tyr Glu Leu Ala Glu Glu Cys Leu Gln Thr Asn Tyr Tyr
130 135 140
Gly Val Lys Arg Thr Ile Asn Ala Leu Leu Pro Leu Leu Gln Phe Ser
145 150 155 160
Asp Ser Pro Arg Ile Val Asn Val Ser Ser Asp Val Gly Leu Leu Lys
165 170 175
Lys Ile Pro Gly Glu Arg Ile Arg Glu Ala Leu Gly Asp Val Glu Lys
180 185 190
Leu Thr Glu Glu Ser Val Asp Gly Ile Leu Asp Glu Phe Leu Arg Asp
195 200 205
Phe Lys Glu Gly Lys Ile Ala Glu Lys Gly Trp Pro Thr Phe Lys Ser
210 215 220
Ala Tyr Ser Ile Ser Lys Ala Ala Leu Asn Ser Tyr Thr Arg Val Leu
225 230 235 240
Ala Arg Lys Tyr Pro Ser Ile Ile Ile Asn Cys Val Cys Pro Gly Val
245 250 255
Val Lys Thr Asp Ile Asn Leu Lys Met Gly His Leu Thr Val Glu Glu
260 265 270
Gly Ala Ala Ser Pro Val Arg Leu Ala Leu Met Pro Leu Gly Ser Pro
275 280 285
Ser Gly Leu Phe Tyr Thr Arg Asn Glu Val Thr Pro Phe Glu
290 295 300
<210> 53
<211> 900
<212> DNA
<213> 菠菜（Spinacia oleracea）
<220>
<221> misc_feature
<223> 核酸分子，其包含编码根据SEQ ID NO 54的酶的核苷酸。SpolFSL
<400> 53
atggctgaac aatccaactt tctggctgaa aaaaggtatg cagtagtgac aggtgcaaac 60
aaaggaatag ggcttgaaat atgcagacag cttgcttctc aaggtgtgat tgtacttatc 120
acttctagag atggaaagaa aggattagaa gcccttaatg atctcattaa atctggaatt 180
agctctgata atcttcatta tcatcagctt gatgttactg accctatgag tattactgct 240
cttgctggtt tcatcaattc caaatttggc aagcttgata ttctggtgaa caatgctggg 300
ataggtggat ttataattga ctacgatgct atcaaagcaa taggttttcg caatatcaat 360
tatgacgaga tgatgacaca aacatatgag cttgcaaaag aatgcttgga aacaaactac 420
tatggagtta agagaacaac tgaagctttg cttcctcagc tggagttatc ggattcacca 480
aggatcatca atgtctcctc ttctacgggg atgttgaaga atataccaaa tgagaggatc 540
agaggagtct tgggtgatgc agagaatctt acagaagaaa aagttgaagc gattttgaat 600
gagttactga cagatttcaa agatggttca ttcaaagaga aagaatggcc ttctagaatg 660
gcagcttata cactgtcaaa ggcggctttg aatgcatatg caagaatatt ggctaagaaa 720
tacccgtcaa ttatcatcag ttgtgtttgt cctggtgtta ctaagacaga tatgaacgga 780
aacttgggac aattaacagt tgaagaaggg gccgcaagtc cggtgagagt agcattgatg 840
cctcatggtt caccttccgg tcttttctat gcaagaagcg aagtttcttc atatgaataa 900
<210> 54
<211> 299
<212> PRT
<213> 菠菜（Spinacia oleracea）
<220>
<221> misc_feature
<223> 氧化还原酶，其能够增强岩藻糖基转移酶的活性（SpolFSL）
<400> 54
Met Ala Glu Gln Ser Asn Phe Leu Ala Glu Lys Arg Tyr Ala Val Val
1 5 10 15
Thr Gly Ala Asn Lys Gly Ile Gly Leu Glu Ile Cys Arg Gln Leu Ala
20 25 30
Ser Gln Gly Val Ile Val Leu Ile Thr Ser Arg Asp Gly Lys Lys Gly
35 40 45
Leu Glu Ala Leu Asn Asp Leu Ile Lys Ser Gly Ile Ser Ser Asp Asn
50 55 60
Leu His Tyr His Gln Leu Asp Val Thr Asp Pro Met Ser Ile Thr Ala
65 70 75 80
Leu Ala Gly Phe Ile Asn Ser Lys Phe Gly Lys Leu Asp Ile Leu Val
85 90 95
Asn Asn Ala Gly Ile Gly Gly Phe Ile Ile Asp Tyr Asp Ala Ile Lys
100 105 110
Ala Ile Gly Phe Arg Asn Ile Asn Tyr Asp Glu Met Met Thr Gln Thr
115 120 125
Tyr Glu Leu Ala Lys Glu Cys Leu Glu Thr Asn Tyr Tyr Gly Val Lys
130 135 140
Arg Thr Thr Glu Ala Leu Leu Pro Gln Leu Glu Leu Ser Asp Ser Pro
145 150 155 160
Arg Ile Ile Asn Val Ser Ser Ser Thr Gly Met Leu Lys Asn Ile Pro
165 170 175
Asn Glu Arg Ile Arg Gly Val Leu Gly Asp Ala Glu Asn Leu Thr Glu
180 185 190
Glu Lys Val Glu Ala Ile Leu Asn Glu Leu Leu Thr Asp Phe Lys Asp
195 200 205
Gly Ser Phe Lys Glu Lys Glu Trp Pro Ser Arg Met Ala Ala Tyr Thr
210 215 220
Leu Ser Lys Ala Ala Leu Asn Ala Tyr Ala Arg Ile Leu Ala Lys Lys
225 230 235 240
Tyr Pro Ser Ile Ile Ile Ser Cys Val Cys Pro Gly Val Thr Lys Thr
245 250 255
Asp Met Asn Gly Asn Leu Gly Gln Leu Thr Val Glu Glu Gly Ala Ala
260 265 270
Ser Pro Val Arg Val Ala Leu Met Pro His Gly Ser Pro Ser Gly Leu
275 280 285
Phe Tyr Ala Arg Ser Glu Val Ser Ser Tyr Glu
290 295
Claims (41)
1.制备QA-FRX(X/A)的方法，其中将FRX(X/A)链添加至QA的C-28位，所述方法包括：
(i)(a)将QA与UDP-α-D-岩藻糖和酶Qs-28-O-FucT(SEQ ID NO 2)或者具有至少70％序列同一性的序列的酶合并以形成QA-F；和/或
(b)将QA与UDP-4-酮,6-脱氧-D-葡萄糖、酶Qs-28-O-FucT(SEQ ID NO 2)或者具有至少70％序列同一性的序列的酶，和酶QsFucSyn(SEQ ID NO 12)或者具有至少45％序列同一性的序列的酶合并以形成QA-F；
(ii)将QA-F与UDP-β-L-鼠李糖和酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有至少70％序列同一性的序列的酶合并以形成QA-FR；
(iii)将QA-FR与UDP-α-D-木糖和酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有至少70％序列同一性的序列的酶合并以形成QA-FRX；和
(iv)将QA-FRX与UDP-α-D-木糖和酶Qs-28-O-XylT4(SEQ ID NO 8)或者具有至少70％序列同一性的序列的酶合并以形成QA-FRXX，和/或将QA-FRX与UDP-α-D-芹菜糖和酶Qs-28-O-ApiT4(SEQ ID NO 10)或者具有至少70％序列同一性的序列的酶合并以形成QA-FRXA。
2.制备QA-Mono-FRX(X/A)、QA-Di-FRX(X/A)和/或QA-Tri(X/R)-FRX(X/A)的方法，其中在C-3位添加Mono、Di或Tri(X/R)链并且在QA的C-28位添加FRX(X/A)链，所述方法包括：
(i)将QA与UDP-α-D-葡糖醛酸和酶QsCSL1(SEQ ID NO 26)或QsCslG2(SEQ ID NO 28)或者具有至少70％序列同一性的序列的酶合并以形成QA-Mono；任选地
(ii)将QA-Mono与UDP-α-D-半乳糖和酶Qs-3-O-GalT(SEQ ID NO 30)或者具有至少70％序列同一性的序列的酶合并以形成QA-Di；任选地
(iii)将QA-Di与UDP-β-L-吡喃鼠李糖和酶DN20529_c0_g2_i8(SEQ ID NO 36)或Qs_0283850(SEQ ID NO 34)，或者Qs-3-O-RhaT/XylT(SEQ ID NO 32)或者具有至少70％序列同一性的序列的酶合并以形成QA-TriR，和/或将QA-Di与UDP-α-D-吡喃木糖和酶Qs_0283870(SEQ ID NO 38)或Qs-3-O-RhaT/XylT(SEQ ID NO 32)或者具有至少70％序列同一性的序列的酶合并以形成QA-TriX；
(iv)(a)将QA-Mono、QA-Di和/或QA-Tri(R/X)与UDP-α-D-岩藻糖和酶Qs-28-O-FucT(SEQ ID NO 2)或者具有至少70％序列同一性的序列的酶合并以形成QA-Mono-F、QA-Di-F和/或QA-Tri(R/X)-F，和/或
(b)将QA-Mono、QA-Di和/或QA-Tri(R/X)与UDP-4-酮,6-脱氧-D-葡萄糖、酶Qs-28-O-FucT(SEQ ID NO 2)或者具有至少70％序列同一性的序列的酶，和酶QsFucSyn(SEQ ID NO12)或者具有至少45％序列同一性的序列的酶合并以形成QA-Mono-F，QA-Di-F和/或QA-Tri(R/X)-F；
(v)将QA-Mono-F、QA-Di-F和/或QA-Tri(R/X)-F与UDP-β-L-鼠李糖和酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有至少70％序列同一性的序列的酶合并以形成QA-Mono-FR、QA-Di-FR和/或QA-Tri(R/X)-FR；
(vi)将QA-Mono-FR、QA-Di-FR和/或QA-Tri(R/X)-FR与UDP-α-D-木糖和酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有至少70％序列同一性的序列的酶合并以形成QA-Mono-FRX、QA-Di-FRX和/或QA-Tri(R/X)-FRX；和
(vii)将QA-Mono-FRX、QA-Di-FRX和/或QA-Tri(R/X)-FRX与UDP-α-D-木糖和酶Qs-28-O-XylT4(SEQ ID NO 8)或者具有至少70％序列同一性的序列的酶合并以形成QA-Mono-FRXX、QA-Di-FRXX和/或QA-Tri(R/X)-FRXX，和/或将QA-Mono-FRX、QA-Di-FRX和/或QA-Tri(R/X)-FRX与UDP-α-D-芹菜糖和酶Qs-28-O-ApiT4(SEQ ID NO 10)或者具有至少70％序列同一性的序列的酶合并以形成QA-Mono-FRXA、QA-Di-FRXA和/或QA-Tri(R/X)-FRXA。
3.在宿主中制备生物合成的3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-呋喃芹菜糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸(QA-TriR-FRXA)的方法，所述方法包括以下步骤：
a)表达QA-TriR生物合成所需的基因，和
b)将编码下列的核酸引入所述宿主：
i.酶Qs-28-O-FucT(SEQ ID NO 2)或者具有与SEQ ID NO 2具有至少70％序列同一性的序列的酶；
ii.酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有与SEQ ID NO 4具有至少70％序列同一性的序列的酶；
iii.酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有与SEQ ID NO 6具有至少70％序列同一性的序列的酶；和
iv.酶Qs-28-O-ApiT4(SEQ ID NO 10)或者具有与SEQ ID NO 10具有至少70％序列同一性的序列的酶。
4.在宿主中制备生物合成的3-O-{α-L-吡喃鼠李糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸(QA-TriR-FRXX)的方法，所述方法包括以下步骤：
a)表达QA-TriR生物合成所需的基因，和
b)将编码下列的核酸引入所述宿主：
i.酶Qs-28-O-FucT(SEQ ID NO 2)或者具有与SEQ ID NO 2具有至少70％序列同一性的序列的酶；
ii.酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有与SEQ ID NO 4具有至少70％序列同一性的序列的酶；
iii.酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有与SEQ ID NO 6具有至少70％序列同一性的序列的酶；和
iv.酶Qs-28-O-XylT4(SEQ ID NO 8)或者具有与SEQ ID NO 8具有至少70％序列同一性的序列的酶。
5.在宿主中制备生物合成的3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-呋喃芹菜糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸(QA-TriX-FRXA)的方法，所述方法包括以下步骤：
a)表达QA-TriX生物合成所需的基因，和
b)将编码下列的核酸引入所述宿主：
i.酶Qs-28-O-FucT(SEQ ID NO 2)或者具有与SEQ ID NO 2具有至少70％序列同一性的序列的酶；
ii.酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有与SEQ ID NO 4具有至少70％序列同一性的序列的酶；
iii.酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有与SEQ ID NO 6具有至少70％序列同一性的序列的酶；和
iv.酶Qs-28-O-ApiT4(SEQ ID NO 10)或者具有与SEQ ID NO 10具有至少70％序列同一性的序列的酶。
6.在宿主中制备生物合成的3-O-{β-D-吡喃木糖基-(1->3)-[β-D-吡喃半乳糖基-(1->2)]-β-D-吡喃葡糖苷酸}-28-O-{β-D-吡喃木糖基-(1->3)-β-D-吡喃木糖基-(1->4)-α-L-吡喃鼠李糖基-(1->2)-β-D-吡喃岩藻糖基酯}-皂皮酸(QA-TriX-FRXX)的方法，所述方法包括以下步骤：
a)表达QA-TriX生物合成所需的基因，和
b)将编码下列的核酸引入所述宿主：
i.酶Qs-28-O-FucT(SEQ ID NO 2)或者具有与SEQ ID NO 2具有至少70％序列同一性的序列的酶；
ii.酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有与SEQ ID NO 4具有至少70％序列同一性的序列的酶；
iii.酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有与SEQ ID NO 6具有至少70％序列同一性的序列的酶；和
iv.酶Qs-28-O-XylT4(SEQ ID NO 8)或者具有与SEQ ID NO 8具有至少70％序列同一性的序列的酶。
7.在宿主中制备生物合成的QA-Tri(X/R)-FRX(X/A)的方法，所述方法包括以下步骤：
a)表达QA-TriX和/或QA-TriR生物合成所需的基因，和
b)将编码下列的核酸引入所述宿主：
i.酶Qs-28-O-FucT(SEQ ID NO 2)或者具有与SEQ ID NO 2具有至少70％序列同一性的序列的酶；
ii.酶Qs-28-O-RhaT(SEQ ID NO 4)或者具有与SEQ ID NO 4具有至少70％序列同一性的序列的酶；
iii.酶Qs-28-O-XylT3(SEQ ID NO 6)或者具有与SEQ ID NO 6具有至少70％序列同一性的序列的酶；和
iv.酶Qs-28-O-XylT4(SEQ ID NO 8)或者具有与SEQ ID NO 8具有至少70％序列同一性的序列的酶，和/或酶Qs-28-O-ApiT4(SEQ ID NO 10)或者具有与SEQ ID NO 10具有至少70％序列同一性的序列的酶。
8.根据权利要求3、权利要求4或权利要求7所述的方法，其中通过引入编码下列的核酸来获得步骤a)中的QA-TriR的生物合成：(i)(a)酶QsCSL1(SEQ ID NO 26)或者具有与SEQID NO 26具有至少70％序列同一性的序列的酶，或者(b)酶QsCslG2(SEQ ID NO 28)或者具有与SEQ ID NO 28具有至少70％序列同一性的序列的酶；(ii)酶Qs-3-O-GalT(SEQ ID NO30)或者具有与SEQ ID NO 30具有至少70％序列同一性的序列的酶和(iii)(a)酶DN20529_c0_g2_i8(SEQ ID NO 36)或者具有与SEQ ID NO 36具有至少70％序列同一性的序列的酶，或者(b)酶Qs_0283850(SEQ ID NO 34)或者具有与SEQ ID NO 34具有至少70％序列同一性的序列的酶，或者(c)酶Qs-3-O-RhaT/XylT(SEQ ID NO 32)或者具有与SEQ ID NO 32具有至少70％序列同一性的序列的酶。
9.根据权利要求5、权利要求6或权利要求7所述的方法，其中通过引入编码下列的核酸来获得步骤a)中的QA-TriX的生物合成：(i)(a)酶QsCSL1(SEQ ID NO 26)或者具有与SEQID NO 26具有至少70％序列同一性的序列的酶，或者(b)酶QsCslG2(SEQ ID NO 28)或者具有与SEQ ID NO 28具有至少70％序列同一性的序列的酶；(ii)酶Qs-3-O-GalT(SEQ ID NO30)或者具有与SEQ ID NO 30具有至少70％序列同一性的序列的酶，和(iii)(a)酶Qs_0283870(SEQ ID NO 38)或者具有与SEQ ID NO 38具有至少70％序列同一性的序列的酶，或者(b)酶Qs-3-O-RhaT/XylT(SEQ ID NO 32)或者具有与SEQ ID NO 32具有至少70％序列同一性的序列的酶。
10.根据权利要求3至9中任一项所述的方法，其中
氨基酸SEQ ID NO 2由核酸SEQ ID NO 1编码；
氨基酸SEQ ID NO 4由核酸SEQ ID NO 3编码；
氨基酸SEQ ID NO 6由核酸SEQ ID NO 5编码；
氨基酸SEQ ID NO 8由核酸SEQ ID NO 7编码；
氨基酸SEQ ID NO 10由核酸SEQ ID NO 9编码。
11.根据权利要求2、8、9或10中任一项所述的方法，其中：
氨基酸SEQ ID NO 26由核酸SEQ ID NO 25编码；
氨基酸SEQ ID NO 28由核酸SEQ ID NO 27编码；
氨基酸SEQ ID NO 30由核酸SEQ ID NO 29编码；
氨基酸SEQ ID NO 32由核酸SEQ ID NO 31编码；
氨基酸SEQ ID NO 34由核酸SEQ ID NO 33编码；
氨基酸SEQ ID NO 36由核酸SEQ ID NO 35编码；
氨基酸SEQ ID NO 38由核酸SEQ ID NO 37编码。
12.根据SEQ ID NO 2的岩藻糖基转移酶(Qs-28-O-FucT)或者具有至少70％序列同一性的序列的酶。
13.根据SEQ ID NO 4的鼠李糖基转移酶(Qs-28-O-RhaT)或者具有至少70％序列同一性的序列的酶。
14.根据SEQ ID NO 6的木糖基转移酶(Qs-28-O-XylT3)或者具有至少70％序列同一性的序列的酶。
15.根据SEQ ID NO 8的木糖基转移酶(Qs-28-O-XylT4)或者具有至少70％序列同一性的序列的酶。
16.根据SEQ ID NO 10的芹菜糖基转移酶(Qs-28-O-ApiT4)或者具有至少70％序列同一性的序列的酶。
17.核酸，编码如权利要求12至16中任一项所述的酶中的任一种。
18.根据权利要求17所述的核酸，进一步编码如权利要求8或9所述的任何酶。
19.载体，包含根据权利要求17或权利要求18所述的核酸。
20.宿主细胞，包含根据权利要求17或权利要求18所述的核酸。
21.用根据权利要求19所述的载体转化的宿主细胞。
22.根据权利要求20或21所述的宿主细胞，其中所述宿主细胞是植物细胞或微生物细胞。
23.植物或微生物的生物系统，包含根据权利要求21或权利要求22所述的宿主细胞。
24.根据权利要求23所述的生物系统，其中所述生物系统是酵母或本氏烟草(Nicotiana benthamiana)。
25.根据SEQ ID NO 12的氧化还原酶(QsFucSyn)或者具有至少45％序列同一性的序列的酶。
26.根据权利要求25所述的氧化还原酶，其中与SEQ ID NO 12(QsFucSyn)具有至少45％序列同一性的酶是QsFSL-1(SEQ ID No.48)、QsFSL-2(SEQ ID No 50)或SoFSL-1(SEQID No 52)中的一种。
27.核酸，编码根据权利要求25或权利要求26所述的酶。
28.根据权利要求1或权利要求2中任一项所述的方法，所述方法具有步骤(i)(b)(权利要求1)或者步骤(iv)(b)(权利要求2)，其中与SEQ ID NO 12(QsFucSyn)具有至少45％序列同一性的酶是根据权利要求26的或者是SpolFSL(SEQ ID NO 54)。
29.根据权利要求3至11中任一项所述的方法，其中步骤b)进一步引入编码根据权利要求25或权利要求26所述的酶中的至少一种或者编码酶SpolFSL(SEQ ID NO 54)的核酸。
30.根据权利要求1或权利要求2中任一项所述的方法，所述方法具有步骤(i)(b)(权利要求1)或者步骤(iv)(b)(权利要求2)，其中UDP-D-葡萄糖与酶ATCV-1(SEQ ID NO 40)或者具有至少55％序列同一性的序列的酶合并以形成所述UDP-4-酮,6-脱氧-D-葡萄糖。
31.根据权利要求29所述的方法，其中步骤b)进一步引入编码酶ATCV-1(SEQ ID NO40)或者具有至少55％序列同一性的序列的酶的核酸。
32.根据SEQ ID NO 14(QsAXS1)的UDP-芹菜糖/UDP-木糖合酶或者具有至少70％序列同一性的序列的酶。
33.核酸，编码根据权利要求32所述的酶。
34.根据权利要求1或权利要求2所述的方法，所述方法具有步骤(i)(b)(权利要求1)或者步骤(iv)(b)(权利要求2)，其中所述步骤(i)(b)(权利要求1)或者步骤(iv)(b)(权利要求2)进一步包括与根据权利要求32所述的酶合并。
35.根据权利要求1至11、28至31和34中任一项所述的方法，其中所述方法进一步包括分离所述QA衍生物的步骤。
36.根据权利要求35所述的方法获得的QA衍生物。
37.根据权利要求36所述的QA衍生物作为佐剂的用途。
38.根据权利要求37所述的用途，其中所述佐剂是脂质体制剂。
39.根据权利要求37或权利要求38所述的用途，其中所述佐剂进一步包含TLR4激动剂。
40.根据权利要求39所述的用途，其中所述TLR4激动剂是3D-MPL。
41.佐剂组合物，包含根据权利要求36所述的QA衍生物。
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