CN108795919B - 一种催化制备udp-鼠李糖的融合酶及其应用 - Google Patents
一种催化制备udp-鼠李糖的融合酶及其应用 Download PDFInfo
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- CN108795919B CN108795919B CN201810549433.0A CN201810549433A CN108795919B CN 108795919 B CN108795919 B CN 108795919B CN 201810549433 A CN201810549433 A CN 201810549433A CN 108795919 B CN108795919 B CN 108795919B
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Abstract
一种催化制备UDP‑鼠李糖的融合酶及其应用，氨基酸序列如SEQ ID NO.4所示。本发明获得了一种能实现辅酶自循环而催化UDP‑葡萄糖生成UDP‑鼠李糖的融合酶VvRHM‑NRS，在反应体系中只需在起始阶段添加少量的NAD+，无需加入NADPH，就可生成UDP‑鼠李糖，这是首次能实现辅酶自循环而合成UDP‑鼠李糖。
Description
技术领域
本发明属于酶工程技术领域，具体涉及一种融合酶的构建及其在催化制备UDP-鼠李糖中的应用。
背景技术
L-鼠李糖是一种6-脱氧几糖，广泛存在于糖蛋白、多糖及次级代谢产物中，并发挥重要的生理活性。糖基化合物的生物合成主要是由各种不同糖基转移酶参与催化。这些酶选择性地转移特异性核苷二磷酸糖的单糖残基合成各种糖基化产物。但真核生物糖基转移酶催化底物仅限于有限几种核苷二磷酸糖，其中尿苷二磷酸糖基就是最重要的生物合成糖甙、寡糖、多糖和糖蛋白等含糖基化合物的糖基供体之一。
UDP-鼠李糖在结构上是由一分子鼠李糖和一分子尿苷二磷酸所组成，是构建鼠李糖基衍生物的重要中间体，因此如何高效合成UDP-鼠李糖一直受到研究人员的关注。利用化学合成法获得UDP-鼠李糖存在得率低、反应专一性差、副产物多等缺点，而生物酶法能很好弥补化学合成的不足。
在植物体内，UDP-鼠李糖合成酶(UDP-rhamnose synthase)通过连续的三步反应催化UDP-葡萄糖生成UDP-鼠李糖。第一步反应是UDP-葡萄糖生成UDP-4-keto-6-deoxy-glucose，同时消耗NAD+生成NADH；第二步反应是UDP-4-keto-6-deoxy-glucose生成UDP-keto-rhamnose；第三步反应是UDP-keto-rhamnose被催化生成UDP-鼠李糖，同时消耗NADPH生成NADP+。由此可见虽然可以在体外利用UDP-鼠李糖合成酶催化UDP-葡萄糖合成UDP-鼠李糖，但必须在反应体系中添加至少与产物量相等的两种辅酶NAD+和NADPH，而NADPH辅酶的价格昂贵，因此该催化体系成本过高(专利申请号：CN201710230581.1；The Journal ofBiological Chmeistry 2007,282(8),5389-5403)。另一种方法是在体外催化系统中分别构建NAD+/NADH及NADP+/NADPH的循环体系，但另外构建两个辅酶的循环体系所需要的酶种类繁多，使得反应体系不具有可行性。因此，比较可行的方法是获得一种UDP-鼠李糖合成酶，该酶可实现辅酶自循环，即第三步反应能利用NADH为辅酶生成NAD+，这样就可与第一步反应组成辅酶自循环系统，彻底解决UDP-鼠李糖合成过程中的辅酶供应问题。
发明内容
解决的技术问题：本发明提供了一种催化制备UDP-鼠李糖的融合酶及其应用，利用蔗糖、UDP及NAD+制备UDP-鼠李糖。
技术方案：一种催化制备UDP-鼠李糖的融合酶，氨基酸序列如SEQ ID NO.4所示。
编码所述融合酶的基因，核苷酸序列如SEQ ID NO.3所示。
含有所述核苷酸序列的重组质粒。
含有所述重组质粒的大肠杆菌。
所述的融合酶与蔗糖合成酶组成双酶催化体系在制备UDP-鼠李糖中的应用。
上述应用的反应体系为50mM pH 8.0的磷酸缓冲液，300mM蔗糖，8mM UDP，1mM NAD+，1mM DTT和0.16mg/mL融合酶及0.02mg/mL蔗糖合成酶，30℃反应48小时，能获得0.57mM的UDP-鼠李糖。
有益效果：1.获得了一种能实现辅酶自循环而催化UDP-葡萄糖生成UDP-鼠李糖的融合酶VvRHM-NRS，在反应体系中只需在起始阶段添加少量的NAD+，无需加入NADPH，就可生成UDP-鼠李糖，这是首次报道能实现辅酶自循环而合成UDP-鼠李糖；
2.利用VvRHM-NRS和GmSUS组成双酶催化体系，该催化体系首次实现了利用蔗糖、UDP及NAD+制备UDP-鼠李糖，无需添加昂贵的底物UDP-葡萄糖，而实现UDP-鼠李糖的制备，可以大幅降低制备成本。
附图说明
图1VvRHM-NRS和GmSUS双酶催化体系制备UDP-鼠李糖示意图；
图2温度及pH对VvRHM活性的影响，(a)温度对酶活的影响，(b)pH对酶活的影响，(c)温度稳定性。
图3NRS/ER对VvRHM催化UDP-葡萄糖生成UDP-鼠李糖的影响，(a)不同条件下生成UDP-鼠李糖的示意图，(b)HPLC检测生成的UDP-鼠李糖，(c)ESI-MS检测生成的UDP-鼠李糖。
图4温度及pH对融合酶VvRHM-NRS活性的影响，(a)温度对酶活的影响，(b)pH对酶活的影响，(c)温度稳定性。
图5反应条件对VvRHM-NRS和GmSUS双酶催化体系制备UDP-鼠李糖的影响，(a)UDP对双酶催化体系制备UDP-鼠李糖的影响，(b)NAD+对双酶催化体系制备UDP-鼠李糖的影响，(c)VvRHM-NRS和GmSUS双酶催化体系制备UDP-鼠李糖的时间曲线。
具体实施方式
以下实施例只为说明本发明的技术构思及特点，其目的在于让熟悉此项技术的人是能够了解本发明的内容并据以实施，并不能以此限制本发明的保护范围。凡根据本发明精神实质所做的等效变换或修饰，都应涵盖在本发明的保护范围之内。
为了进一步理解本发明，下面结合实施例对本发明进行详细阐述，其中，如无特殊说明，实施例中涉及的各种反应试剂均可以通过商业渠道购买得到；如无特殊说明，实施例中涉及的具体操作参见《分子克隆实验指南第三版》。
本发明利用来源于Vitis vinifera的UDP-鼠李糖合成酶VvRHM和来源于Arabidopsis thaliana的双功能酶UDP-4-keto-6-deoxy-D-glucose 3,5-epimerase/UDP-4-keto-rhamnose 4-keto-reductase(NRS/ER)构建一种融合酶VvRHM-NRS。该融合酶VvRHM-NRS催化第三步反应生成UDP-鼠李糖时能利用辅酶NADH，而无需消耗NADPH，因此该融合酶进行催化反应时能实现辅酶自循环，仅需在反应开始阶段添加少量的NAD+，就能实现催化UDP-葡萄糖生成UDP-鼠李糖。随后通过与Glycine max来源的蔗糖合成酶GmSUS组成双酶催化体系能利用蔗糖、UDP及NAD+制备UDP-鼠李糖(图1)。该体系可用于生产制备各种鼠李糖基衍生物，具有很好的应用前景。
实施例1
1.Vitis vinifera来源的UDP-鼠李糖合成酶VvRHM的克隆、表达及定性
1.1 VvRHM基因的优化合成及重组质粒构建
对Vitis vinifera来源的UDP-鼠李糖合成酶VvRHM基因(XP_002285634.1)按照大肠杆菌K12优势密码子表(http://www.kazusa.or.jp/codon/)对上述基因序列进行优化，选择氨基酸同义密码子使用频率高的密码子作为优势密码子，最终获得优化后的酶基因序列信息，由上海捷瑞生物工程有限公司合成，并在基因的N端和C端分别添加Nco I和BamH I酶切位点，并在其C端融合6个组氨酸标签，获得优化后的VvRHM基因，其核酸序列分别为SEQID NO:1所示。
将优化后的VvRHM基因用Nco I和BamH I双酶切，同时将重组质粒pCDFDuet-1也用Nco I和BamH I双酶切，并分别割胶回收，浓缩后16℃连接过夜，将连接产物转化大肠杆菌JM109感受态细胞，筛选阳性克隆，进行序列分析；挑选序列正确的克隆提取质粒，获得重组质粒pCDFDuet-VvRHM。
1.2 VvRHM的重组表达、纯化及定性
1.2.1 VvRHM的重组表达、纯化
将重组质粒pCDFDuet-VvRHM转化大肠杆菌BL21(DE3)宿主菌(Novagen)，在含有链霉素(50μg/mL)的LB平板(LB培养基：胰蛋白胨10g/L，酵母提取物5g/L，NaCl 5g/L，琼脂15g/L)上经过37℃培养过夜，挑转化子到200mL的LB培养基中(50μg/mL链霉素)37℃，200rpm振荡培养至OD600为0.6时，加入终浓度为0.1mM异丙基β-D-硫代吡喃半乳糖苷(IPTG)诱导剂，20℃培养24h，用高速冷冻离心机将培养液在4℃下，以13,000rpm离心15min，收集菌体。再用Ni-NTA亲和层析柱进行纯化最终得到纯化的VvRHM，具体纯化过程参考Novogen公司的说明书。
1.2.2 VvRHM酶活测定
反应体系100μL包括：50mM磷酸缓冲pH 8.0，1mM UDP-葡萄糖，1mM NAD+，1mMNADPH，1mM DTT和适量的VvRHM，35℃反应30分钟。沸水浴3分钟终止反应。UDP-鼠李糖的量利用HPLC检测，酶活力单位(U)定义为：在测定条件下，每分钟产生1μmol UDP-鼠李糖所用的酶量为1个酶活力单位。
HPLC分析UDP-鼠李糖：Agilent 1260Infinity；分析柱为Develosil RPAQUEOUSreverse phase column(250x 4.6mm,Nomura Chemical Co.)，流动相为20mM三乙基乙酸铵缓冲液pH7.0；流速为1.0mL/min；DAD检测器检测波长为260nm。
1.2.3 VvRHM的酶学性质
在25-45℃范围内，每隔5℃，分别测定酶活。缓冲为50mmol/L磷酸缓冲液，pH 8.0，发现UDP-鼠李糖合成酶VvRHM的最适反应温度为40℃(图2-a)。
在不同的pH(6.5-8.5，50mmol/L磷酸缓冲液)条件下，40℃分别测定酶活，发现UDP-鼠李糖合成酶VvRHM的最适反应pH为8.0(图2-b)。
在pH 8.0，50mmol/L磷酸缓冲液条件下，30℃或35℃分别保温30，60，90及120分钟，分别测定残存酶活，发现VvRHM在30℃，pH 8.0条件下，稳定性较好(图2-c)。
在pH 8.0，40℃最适条件下，以不同浓度的NAD+，NADPH及UDP-葡萄糖为底物，测定酶活，再以双倒数作图法获得UDP-鼠李糖合成酶VvRHM对NAD+的米氏常数Km为5.6±0.6μM，最大反应速度Kmax为11.1±0.8nmol/min/mg；对NADPH的米氏常数Km为82.3±9μM，最大反应速度20.8±0.8nmol/min/mg；对UDP-葡萄糖的米氏常数Km为100±8μM，最大反应速度Kmax为17.4±0.9nmol/min/mg。
2.Arabidopsis thaliana来源的双功能酶NRS/ER的克隆、表达
2.1 NRS/ER基因的优化合成及重组质粒构建
对Arabidopsis thaliana来源的双功能酶NRS/ER基因(NP_564806.1)按照大肠杆菌K12优势密码子表(http://www.kazusa.or.jp/codon/)对上述基因序列进行优化，选择氨基酸同义密码子使用频率高的密码子作为优势密码子，最终获得优化后的酶基因序列信息，由上海捷瑞生物工程有限公司合成，并在基因的N端和C端分别添加Nco I和BamH I酶切位点，并在其C端融合6个组氨酸标签，获得优化后的NRS/ER基因，其核酸序列分别为SEQ IDNO:2所示。
将优化后的NRS/ER基因用Nco I和BamH I双酶切，同时将重组质粒pCDFDuet-1也用Nco I和BamH I双酶切，并分别割胶回收，浓缩后16℃连接过夜，将连接产物转化大肠杆菌JM109感受态细胞，筛选阳性克隆，进行序列分析；挑选序列正确的克隆提取质粒，获得重组质粒pCDFDuet-NRS/ER。
2.2 NRS/ER的重组表达及纯化
将重组质粒pCDFDuet-NRS/ER转化大肠杆菌BL21(DE3)宿主菌(Novagen)，在含有链霉素(50μg/mL)的LB平板(LB培养基：胰蛋白胨10g/L，酵母提取物5g/L，NaCl 5g/L，琼脂15g/L)上经过37℃培养过夜，挑转化子到200mL的LB培养基中(50μg/mL链霉素)37℃，200rpm振荡培养至OD600为0.6时，加入终浓度为0.1mM异丙基β-D-硫代吡喃半乳糖苷(IPTG)诱导剂，20℃培养24h，用高速冷冻离心机将培养液在4℃下，以13,000rpm离心15min，收集菌体。再用Ni-NTA亲和层析柱进行纯化最终得到纯化的双功能酶NRS/ER，具体纯化过程参考Novogen公司的说明书。
3.NRS/ER对VvRHM催化UDP-葡萄糖生成UDP-鼠李糖的影响
双功能酶NRS/ER的酶学特性是催化UDP-4-keto-6-deoxy-glucose经UDP-keto-rhamnose生成UDP-鼠李糖，该功能与UDP-鼠李糖合成酶催化的第二步和第三步反应相同。
反应体系100μL包括：50mM磷酸缓冲pH 8.0，1mM UDP-葡萄糖，1mM NAD+，1mM DTT和0.16mg/mL VvRHM及0.2mg/mL NRS/ER，分析UDP-鼠李糖的合成情况。研究发现，NRS/ER的加入使VvRHM能在没有NADPH的情况下也能合成UDP-鼠李糖，而且UDP-鼠李糖的产量大幅度提升，提升幅度为167％(图3-a)。对合成的UDP-鼠李糖进行HPLC分析，研究发现，当反应体系中添加NADPH时，在17.548分钟处出现了一个新的峰，而不添加NADPH没有新的峰产生，而如果加入NRS/ER在该处又出现新的峰(图3-b)。进一步对合成的UDP-鼠李糖进行电喷雾电离质谱(ESI-MS)分析，发现新产生的峰的[M-H]-分子量为549.0532，与UDP-鼠李糖的理论分子量一致(图3-c)。由此可见NRS/ER的加入使的反应体系能够不消耗NADPH而合成UDP-鼠李糖。
4.融合酶VvRHM-NRS的构建
对UDP-鼠李糖合成酶VvRHM的氨基酸序列进行分析，发现其主要分为两部分，分别为N端结构域(VvRHM-N，氨基酸从1到376)和C端结构域(VvRHM-C，氨基酸从377-675)。分析表明VvRHM-N的功能是催化第一步反应：催化UDP-葡萄糖生成UDP-4-keto-6-deoxy-glucose，同时消耗NAD+生成NADH；VvRHM-C的功能是催化第二及第三步反应：催化UDP-4-keto-6-deoxy-glucose经UDP-keto-rhamnose生成UDP-鼠李糖，同时消耗NADPH生成NADP+。而上文研究结果可知，将VvRHM-N和NRS/ER进行融合，构建融合酶VvRHM-NRS，该融合酶VvRHM-NRS有望仅需在反应开始阶段添加少量的NAD+，就能实现催化UDP-葡萄糖生成UDP-鼠李糖。
以pCDFDuet-VvRHM为模板，设计引物如下：VvRHM-N-1：CATGCCATGGCAACCCATACCCCGAAAAA，VvRHM-N-2：CGCGGATCCCACCGGCACAACCATGCGGGTCTG，下划线表示酶切位点。引物由上海生物工程有限公司合成。PCR扩增的条件是95℃，5min；暂停计时，加Pyrobest聚合酶，加40μL石蜡油密封；35次循环(94℃，50s；52℃，90s；72℃，1min)；72℃，10min；反应停止，4℃保温。通过凝胶回收试剂盒对PCR扩增产物进行纯化。得到基因片段和pET-28a分别用Nco I和BamH I进行双酶切，并分别割胶回收，浓缩后16℃连接过夜，将连接产物转化大肠杆菌JM109感受态细胞，筛选阳性克隆，进行序列分析；挑选序列正确的克隆提取质粒，获得重组质粒pET-VvRHM-N。
以pCDFDuet-NRS/ER为模板，设计引物如下：NRS/ER-1：CGCGGATCCACAATGGTTGCAGATGCCAATGGT，NRS/ER-2：CCGCTCGAGTGCTTTAACTTCTGTCTT，下划线表示酶切位点。引物由上海生物工程有限公司合成。PCR扩增的条件是95℃，5min；暂停计时，加Pyrobest聚合酶，加40μL石蜡油密封；35次循环(94℃，50s；52℃，90s；72℃，1min)；72℃，10min；反应停止，4℃保温。通过凝胶回收试剂盒对PCR扩增产物进行纯化。得到基因片段和pET-VvRHM-N分别用BamH I和Hind III进行双酶切，并分别割胶回收，浓缩后16℃连接过夜，将连接产物转化大肠杆菌JM109感受态细胞，筛选阳性克隆，进行序列分析；挑选序列正确的克隆提取质粒，获得重组质粒pET-VvRHM-NRS。融合酶VvRHM-NRS的核酸序列如SEQ ID NO:3所示，其氨基酸序列如SEQ ID NO:4所示。
5.融合酶VvRHM-NRS的表达、定性
5.1 VvRHM-NRS的重组表达、纯化
将重组质粒pET-VvRHM-NRS转化大肠杆菌BL21(DE3)宿主菌(Novagen)，在含有卡那霉素(50μg/mL)的LB平板(LB培养基：胰蛋白胨10g/L，酵母提取物5g/L，NaCl 5g/L，琼脂15g/L)上经过37℃培养过夜，挑转化子到200mL的LB培养基中(50μg/mL卡那霉素)37℃，200rpm振荡培养至OD600为0.6时，加入终浓度为0.1mM异丙基β-D-硫代吡喃半乳糖苷(IPTG)诱导剂，20℃培养24h，用高速冷冻离心机将培养液在4℃下，以13,000rpm离心15min，收集菌体。再用Ni-NTA亲和层析柱进行纯化最终得到纯化的VvRHM-NRS，具体纯化过程参考Novogen公司的说明书。
5.2 VvRHM-NRS酶活测定
反应体系100μL包括：50mM磷酸缓冲pH 8.0，1mM UDP-葡萄糖，1mM NAD+，1mM DTT和适量的VvRHM-NRS,35℃反应30分钟。沸水浴3分钟终止反应。UDP-鼠李糖的量通过HPLC检测，酶活力单位(U)定义为：在测定条件下，每分钟产生1μmol UDP-鼠李糖所用的酶量为1个酶活力单位。
HPLC分析UDP-鼠李糖：Agilent 1260Infinity；分析柱为Develosil RPAQUEOUSreverse phase column(250x 4.6mm,Nomura Chemical Co.)，流动相为20mM三乙基乙酸铵缓冲液pH 7.0；流速为1.0mL/min；DAD检测器检测波长为260nm。
5.3 VvRHM-NRS的酶学性质
在25-45℃范围内，每隔5℃，分别测定酶活。缓冲为50mmol/L磷酸缓冲液，pH 8.0，发现VvRHM-NRS的最适反应温度为30℃(图4-a)。
在不同的pH(6.5-8.5，50mmol/L磷酸缓冲液)条件下，40℃分别测定酶活，发现VvRHM-NRS的最适反应pH为7.5-8.0(图4-b)。
在pH 8.0，50mmol/L磷酸缓冲液条件下，30℃或35℃分别保温30，60，90及120分钟，分别测定残存酶活，发现VvRHM-NRS在30℃，pH 8.0条件下，稳定性较好(图4-c)。
在pH 8.0，30℃最适条件下，以不同浓度的NAD+及UDP-葡萄糖为底物，测定酶活，再以双倒数作图法获得UDP-鼠李糖合成酶VvRHM对NAD+的米氏常数Km为69±7μM，最大反应速度Kmax为11.9±0.5nmol/min/mg；对UDP-葡萄糖的米氏常数Km为88±9μM，最大反应速度Kmax为12.7±0.6nmol/min/mg。由此可见融合酶可仅以NAD+为辅酶催化UDP-葡萄糖生成UDP-鼠李糖。
6.融合酶VvRHM-NRS与GmSUS双酶催化体系的构建及转化条件研究
Glycine max来源的蔗糖合成酶GmSUS能以蔗糖和UDP为底物生成UDP-葡萄糖和果糖，将融合酶VvRHM-NRS与GmSUS构建双酶催化体系就可以蔗糖和UDP为底物合成UDP-鼠李糖，从而可以避免添加价格也很昂贵的UDP-葡萄糖，从而可以大幅降低成本。
6.1 GmSUS的制备
对Glycine max来源的蔗糖合成酶GmSUS基因(NP_001237525.1)按照大肠杆菌K12优势密码子表(http://www.kazusa.or.jp/codon/)对上述基因序列进行优化，选择氨基酸同义密码子使用频率高的密码子作为优势密码子，最终获得优化后的酶基因序列信息，由上海捷瑞生物工程有限公司合成，并在基因的N端和C端分别添加Nco I和EcoR I酶切位点，并在其C端融合6个组氨酸标签，获得优化后的GmSUS基因，其核酸序列分别为SEQ ID NO:5所示。
将优化后的GmSUS基因用Nco I和EcoR I双酶切，同时将重组质粒pACYCDuet-1也用Nco I和EcoR I双酶切，并分别割胶回收，浓缩后16℃连接过夜，将连接产物转化大肠杆菌JM109感受态细胞，筛选阳性克隆，进行序列分析；挑选序列正确的克隆提取质粒，获得重组质粒pACYCDuet-GmSUS。
将重组质粒pACYCDuet-GmSUS转化大肠杆菌BL21(DE3)宿主菌(Novagen)，在含有氯霉素(35μg/mL)的LB平板(LB培养基：胰蛋白胨10g/L，酵母提取物5g/L，NaCl 5g/L，琼脂15g/L)上经过37℃培养过夜，挑转化子到200mL的LB培养基中(35μg/mL氯霉素)37℃，200rpm振荡培养至OD600为0.6时，加入终浓度为0.1mM异丙基β-D-硫代吡喃半乳糖苷(IPTG)诱导剂，20℃培养24h，用高速冷冻离心机将培养液在4℃下，以13,000rpm离心15min，收集菌体。再用Ni-NTA亲和层析柱进行纯化最终得到纯化的GmSUS，具体纯化过程参考Novogen公司的说明书。
6.2 VvRHM-NRS与GmSUS双酶催化体系的构建
反应体系100μL包括：50mM磷酸缓冲pH 8.0，300mM蔗糖，1mM UDP，1mM NAD+，1mMDTT和适量的VvRHM-NRS与GmSUS,30℃反应30分钟。沸水浴3分钟终止反应。UDP-鼠李糖的量通过HPLC检测，测定方法同上面所述。研究发现利用VvRHM-NRS和GmSUS组成双酶催化体系，可利用蔗糖、UDP及NAD+制备UDP-鼠李糖，无需添加昂贵的底物UDP-葡萄糖，而实现UDP-鼠李糖的制备，可以大幅降低制备成本。
6.3 VvRHM-NRS与GmSUS比例对催化体系的影响
反应体系100μL包括：50mM磷酸缓冲pH 8.0，300mM蔗糖，1mM UDP，1mM NAD+，1mMDTT，0.04-0.2mg/mL VvRHM-NRS及0.02mg/mL GmSUS,30℃反应1h。沸水浴3分钟终止反应。UDP-鼠李糖的量通过HPLC检测，测定方法同上面所述。结果如表1所示，随着VvRHM-NRS浓度的增加，UDP-鼠李糖的生产速率大幅增加。当VvRHM-NRS浓度达到0.16mg/mL时，UDP-鼠李糖的生产速率是VvRHM-NRS浓度为0.04mg/mL的365％。但继续增加VvRHM-NRS浓度，UDP-鼠李糖的生产速率没有继续增加，因此双酶的比例(VvRHM-NRS：GmSUS)为8:1。
表1 双酶比例对催化体系生成产物的影响
6.4 pH及温度对VvRHM-NRS与GmSUS双酶催化体系的影响
反应体系100μL包括：50mM磷酸缓冲pH 7.0-9.0，300mM蔗糖，1mM UDP，1mM NAD+，1mM DTT，0.16mg/mL VvRHM-NRS及0.02mg/mL GmSUS,温度为25-45℃反应1h。。沸水浴3分钟终止反应。UDP-鼠李糖的量通过HPLC检测，测定方法同上面所述。研究发现双酶催化体系的最适反应pH为8.0，最适反应温度为35℃，但由于30℃时VvRHM-NRS具有更好的稳定性，因此双酶催化体系的反应温度为30℃。
6.5 UDP对VvRHM-NRS与GmSUS双酶催化体系的影响
反应体系100μL包括：50mM磷酸缓冲pH 8.0，300mM蔗糖，1-32mM UDP，1mM NAD+，1mM DTT和0.16mg/mL VvRHM-NRS及0.02mg/mL GmSUS,30℃反应24h。沸水浴3分钟终止反应。UDP-鼠李糖的量通过HPLC检测，测定方法同上面所述。结果如图5-a所示，发现添加8mMUDP，UDP-鼠李糖的产量最高。进一步加大UDP的量，UDP-鼠李糖的产量反而下降。
6.6 NAD+对VvRHM-NRS与GmSUS双酶催化体系的影响
反应体系100μL包括：50mM磷酸缓冲pH 8.0，300mM蔗糖，8mM UDP，0.1-16mM NAD+，1mM DTT和0.16mg/mL VvRHM-NRS及0.02mg/mL GmSUS,30℃反应24h。沸水浴3分钟终止反应。UDP-鼠李糖的量通过HPLC检测，测定方法同上面所述。结果如图5-b所示，研究发现添加1mM NAD+，UDP-鼠李糖的产量最高。进一步加大UDP的量，UDP-鼠李糖的产量反而下降。
6.7 VvRHM-NRS与GmSUS双酶催化体系生成UDP-鼠李糖的时间曲线
反应体系100μL包括：50mM磷酸缓冲pH 8.0，300mM蔗糖，8mM UDP，1mM NAD+，1mMDTT和0.16mg/mL VvRHM-NRS及0.02mg/mL GmSUS,30℃反应48h。沸水浴3分钟终止反应。UDP-鼠李糖的量通过HPLC检测，测定方法同上面所述。结果如图5-c所示，0至4小时内UDP-鼠李糖的比生产速率为13.2μM/h，4至8小时内UDP-鼠李糖的比生产速率为23.5μM/h，8至12小时内UDP-鼠李糖的比生产速率为28.5μM/h。随后，由于UDP-鼠李糖浓度的增加，产生了抑制作用，UDP-鼠李糖的比生产速率大幅下降，最终经过48h的反应共有0.57mM的UDP-鼠李糖生成。
序列表
<120> 一种催化制备UDP-鼠李糖的融合酶及其应用
<160> 9
<170> SIPOSequenceListing 1.0
<210> 1
<211> 2046
<212> DNA
<213> VvRHM基因(Vitis vinifera)
<400> 1
atggcaaccc ataccccgaa aaatattctg attaccggcg cagcaggctt tattgcatca 60
catgttgcaa atcgtctgat tcgcaattat ccggattata aaattgttgt tctggataaa 120
ctggattatt gtagtaatct gaaaaatctg ctgccgtcta aatctagtcc gaattttaaa 180
tttgttaaag gcgatattgg tagcgcggat ctggttaatt ttctgctgat taccgaatca 240
attgatacca ttatgcattt tgcagcacag acccatgtgg ataatagctt tggcaatagc 300
tttgaattta ccaaaaataa tatttatggg actcatgttc tgctggaagc atgtaaagtg 360
accggccaga ttcgtcgctt tattcatgtg agcaccgatg aagtgtatgg cgaaaccgat 420
gaagatgcag tggtgggtaa tcatgaagca tcacagctgc tgccgaccaa tccgtatagc 480
gcaaccaaag caggtgcaga aatgctggtt atggcttatg gtcgctctta tggcctgccg 540
gttattacca cccgcggcaa taatgtgtat ggcccgaatc agtttccgga aaaactgatt 600
ccgaaattta ttctgctggc aatgcgcggt aaaccgctgc cgattcatgg cgatggctct 660
aatgttcgta gctatctgta ttgtgaagat gttgcagaag catttgaagt tattctgcat 720
cgcggcgaag tgggtcatgt gtataatatt gggaccaaaa aagaacgtcg cgtgattgat 780
gttgcaaaag atgtttgtaa tctgtttagt atggacccgg aaacctctat taaatttgtg 840
gaaaatcgcc cgtttaatga tcagcgctat tttctggatg atcagaaact gaaaattctg 900
ggttggagcg aacgcaccac ctggcaggaa ggcctgaaaa aaacgatgga atggtatatt 960
aataatccga attggtgggg cgatgtgagc ggcgcactgc tgccgcatcc gcgtatgctg 1020
atgatgccgg gcggcattga acgccatttt gatggctcag aagatagcga tagcaccgca 1080
agcccggtgt caagtaatct gaatcagacc cgcatggttg tgccggtgcc gaaaagcgtg 1140
tcaagcccgc gtaaaccgtc actgaaattt ctgctgtatg gtcgtaccgg atggattggc 1200
ggcctgctgg gtaaactgtg tgaaaaacag ggcattccgt atgaatatgg tcgcggtcgc 1260
ctggaagatc gtgcaagcct gctggcagat attcagaatg ttaaaccgac ccatgtgttt 1320
aatgcagcag gcgtgacggg acgcccgaat gtggattggt gtgaatctca taaaccggaa 1380
accattcgtg caaatgttgc agggactctg accctggcag atgtgtgtcg cgaacatggc 1440
ctgctgatga tgaattttgc aactgggtgt atttttgaat atgatgcagc acatccggaa 1500
ggctcaggta ttggctttaa agaagaagat accccgaatt ttgcaggctc tttttatagt 1560
aaaaccaaag caatggtgga agaactgctg aaagaatttg ataatgtttg taccctgcgc 1620
gttcgtatgc cgattagtag cgatctgaat aatccgcgca attttattac caaaatttca 1680
cgctataata aagtggttaa tattccgaat agtatgaccg ttctggatga actgctgccg 1740
attagcattg aaatggcaaa acgtaattgt cgcggcattt ggaattttac caatccgggc 1800
gtggtgagtc ataatgaaat tctggaaatg tataaaagct atattgatcc gaattttaaa 1860
tgggcaaatt ttaccctgga agaacaggca aaagttattg ttgcagcacg ctctaataat 1920
gaaatggatg catctaaact gaaaaatgaa tttccggaac tgctgccgat taaagatagt 1980
ctgattaaat atgtgtttga accgaatcag aaatcactgg cagcacatca tcaccatcac 2040
cattaa 2046
<210> 2
<211> 924
<212> DNA
<213> NRS/ER基因(Arabidopsis thaliana)
<400> 2
atggttgcag atgccaatgg ttcaagctct agtagcttta attttctgat ctatggcaaa 60
acgggttgga tcggcggcct gttaggtaaa ctgtgcgaag cccagggcat tacatatact 120
tatggtagcg gtcgcttaca agatcgtcag tctattgttg ccgatattga atcagttaaa 180
ccgtctcatg tgtttaatgc agcgggcgtg acaggtcgtc ctaatgttga ttggtgcgaa 240
tcacataaag tggaaaccat tcgtacgaat gtggccggca cgttaacatt agccgatata 300
tgtcgcgaaa aaggcttagt gctgatcaat tatgcgacgg gttgtatctt tgaatatgat 360
tcaggtcatc cgctgggcag cggtattggc tttaaagaag aagatacacc gaattttacc 420
ggtagctttt attccaagac caaagcaatg gtggaagaac tgctgaaaaa ttatgaaaat 480
gtttgcaccc tgcgcgtaag aatgcctatt tcttctgatc tgaccaatcc tcgtaatttt 540
atcaccaaaa tcgcccgcta tgaaaaagtt gtggatattc ctaatagcat gacgattctg 600
gatgaactgc tgcctatcag catcgaaatg gctaaacgca atctgaccgg catctataat 660
tttacgaatc caggcgtggt gagtcataac gaaatcttag aaatgtatcg cgattatatc 720
gatccgagct ttacctggaa aaattttacc ttagaagaac aggccaaagt gattgtggct 780
ccacgcagca acaacgaact ggatgctacc aaactgaaaa cagaatttcc ggaactgatg 840
agtatcaaag aatctctgat caaatttgtg tttgaaccta acaaaaagac agaagttaaa 900
gcacaccatc accatcacca ttaa 924
<210> 3
<211> 2043
<212> DNA
<213> 人工序列(Artificial Sequence)
<400> 3
atggcaaccc ataccccgaa aaatattctg attaccggcg cagcaggctt tattgcatca 60
catgttgcaa atcgtctgat tcgcaattat ccggattata aaattgttgt tctggataaa 120
ctggattatt gtagtaatct gaaaaatctg ctgccgtcta aatctagtcc gaattttaaa 180
tttgttaaag gcgatattgg tagcgcggat ctggttaatt ttctgctgat taccgaatca 240
attgatacca ttatgcattt tgcagcacag acccatgtgg ataatagctt tggcaatagc 300
tttgaattta ccaaaaataa tatttatggg actcatgttc tgctggaagc atgtaaagtg 360
accggccaga ttcgtcgctt tattcatgtg agcaccgatg aagtgtatgg cgaaaccgat 420
gaagatgcag tggtgggtaa tcatgaagca tcacagctgc tgccgaccaa tccgtatagc 480
gcaaccaaag caggtgcaga aatgctggtt atggcttatg gtcgctctta tggcctgccg 540
gttattacca cccgcggcaa taatgtgtat ggcccgaatc agtttccgga aaaactgatt 600
ccgaaattta ttctgctggc aatgcgcggt aaaccgctgc cgattcatgg cgatggctct 660
aatgttcgta gctatctgta ttgtgaagat gttgcagaag catttgaagt tattctgcat 720
cgcggcgaag tgggtcatgt gtataatatt gggaccaaaa aagaacgtcg cgtgattgat 780
gttgcaaaag atgtttgtaa tctgtttagt atggacccgg aaacctctat taaatttgtg 840
gaaaatcgcc cgtttaatga tcagcgctat tttctggatg atcagaaact gaaaattctg 900
ggttggagcg aacgcaccac ctggcaggaa ggcctgaaaa aaacgatgga atggtatatt 960
aataatccga attggtgggg cgatgtgagc ggcgcactgc tgccgcatcc gcgtatgctg 1020
atgatgccgg gcggcattga acgccatttt gatggctcag aagatagcga tagcaccgca 1080
agcccggtgt caagtaatct gaatcagacc cgcatggttg tgccggtggg atccacaatg 1140
gttgcagatg ccaatggttc aagctctagt agctttaatt ttctgatcta tggcaaaacg 1200
ggttggatcg gcggcctgtt aggtaaactg tgcgaagccc agggcattac atatacttat 1260
ggtagcggtc gcttacaaga tcgtcagtct attgttgccg atattgaatc agttaaaccg 1320
tctcatgtgt ttaatgcagc gggcgtgaca ggtcgtccta atgttgattg gtgcgaatca 1380
cataaagtgg aaaccattcg tacgaatgtg gccggcacgt taacattagc cgatatatgt 1440
cgcgaaaaag gcttagtgct gatcaattat gcgacgggtt gtatctttga atatgattca 1500
ggtcatccgc tgggcagcgg tattggcttt aaagaagaag atacaccgaa ttttaccggt 1560
agcttttatt ccaagaccaa agcaatggtg gaagaactgc tgaaaaatta tgaaaatgtt 1620
tgcaccctgc gcgtaagaat gcctatttct tctgatctga ccaatcctcg taattttatc 1680
accaaaatcg cccgctatga aaaagttgtg gatattccta atagcatgac gattctggat 1740
gaactgctgc ctatcagcat cgaaatggct aaacgcaatc tgaccggcat ctataatttt 1800
acgaatccag gcgtggtgag tcataacgaa atcttagaaa tgtatcgcga ttatatcgat 1860
ccgagcttta cctggaaaaa ttttacctta gaagaacagg ccaaagtgat tgtggctcca 1920
cgcagcaaca acgaactgga tgctaccaaa ctgaaaacag aatttccgga actgatgagt 1980
atcaaagaat ctctgatcaa atttgtgttt gaacctaaca aaaagacaga agttaaagca 2040
taa 2043
<210> 4
<211> 680
<212> PRT
<213> VvRHM-NRS的氨基酸序列(Artificial Sequence)
<400> 4
Met Ala Thr His Thr Pro Lys Asn Ile Leu Ile Thr Gly Ala Ala Gly
1 5 10 15
Phe Ile Ala Ser His Val Ala Asn Arg Leu Ile Arg Asn Tyr Pro Asp
20 25 30
Tyr Lys Ile Val Val Leu Asp Lys Leu Asp Tyr Cys Ser Asn Leu Lys
35 40 45
Asn Leu Leu Pro Ser Lys Ser Ser Pro Asn Phe Lys Phe Val Lys Gly
50 55 60
Asp Ile Gly Ser Ala Asp Leu Val Asn Phe Leu Leu Ile Thr Glu Ser
65 70 75 80
Ile Asp Thr Ile Met His Phe Ala Ala Gln Thr His Val Asp Asn Ser
85 90 95
Phe Gly Asn Ser Phe Glu Phe Thr Lys Asn Asn Ile Tyr Gly Thr His
100 105 110
Val Leu Leu Glu Ala Cys Lys Val Thr Gly Gln Ile Arg Arg Phe Ile
115 120 125
His Val Ser Thr Asp Glu Val Tyr Gly Glu Thr Asp Glu Asp Ala Val
130 135 140
Val Gly Asn His Glu Ala Ser Gln Leu Leu Pro Thr Asn Pro Tyr Ser
145 150 155 160
Ala Thr Lys Ala Gly Ala Glu Met Leu Val Met Ala Tyr Gly Arg Ser
165 170 175
Tyr Gly Leu Pro Val Ile Thr Thr Arg Gly Asn Asn Val Tyr Gly Pro
180 185 190
Asn Gln Phe Pro Glu Lys Leu Ile Pro Lys Phe Ile Leu Leu Ala Met
195 200 205
Arg Gly Lys Pro Leu Pro Ile His Gly Asp Gly Ser Asn Val Arg Ser
210 215 220
Tyr Leu Tyr Cys Glu Asp Val Ala Glu Ala Phe Glu Val Ile Leu His
225 230 235 240
Arg Gly Glu Val Gly His Val Tyr Asn Ile Gly Thr Lys Lys Glu Arg
245 250 255
Arg Val Ile Asp Val Ala Lys Asp Val Cys Asn Leu Phe Ser Met Asp
260 265 270
Pro Glu Thr Ser Ile Lys Phe Val Glu Asn Arg Pro Phe Asn Asp Gln
275 280 285
Arg Tyr Phe Leu Asp Asp Gln Lys Leu Lys Ile Leu Gly Trp Ser Glu
290 295 300
Arg Thr Thr Trp Gln Glu Gly Leu Lys Lys Thr Met Glu Trp Tyr Ile
305 310 315 320
Asn Asn Pro Asn Trp Trp Gly Asp Val Ser Gly Ala Leu Leu Pro His
325 330 335
Pro Arg Met Leu Met Met Pro Gly Gly Ile Glu Arg His Phe Asp Gly
340 345 350
Ser Glu Asp Ser Asp Ser Thr Ala Ser Pro Val Ser Ser Asn Leu Asn
355 360 365
Gln Thr Arg Met Val Val Pro Val Gly Ser Thr Met Val Ala Asp Ala
370 375 380
Asn Gly Ser Ser Ser Ser Ser Phe Asn Phe Leu Ile Tyr Gly Lys Thr
385 390 395 400
Gly Trp Ile Gly Gly Leu Leu Gly Lys Leu Cys Glu Ala Gln Gly Ile
405 410 415
Thr Tyr Thr Tyr Gly Ser Gly Arg Leu Gln Asp Arg Gln Ser Ile Val
420 425 430
Ala Asp Ile Glu Ser Val Lys Pro Ser His Val Phe Asn Ala Ala Gly
435 440 445
Val Thr Gly Arg Pro Asn Val Asp Trp Cys Glu Ser His Lys Val Glu
450 455 460
Thr Ile Arg Thr Asn Val Ala Gly Thr Leu Thr Leu Ala Asp Ile Cys
465 470 475 480
Arg Glu Lys Gly Leu Val Leu Ile Asn Tyr Ala Thr Gly Cys Ile Phe
485 490 495
Glu Tyr Asp Ser Gly His Pro Leu Gly Ser Gly Ile Gly Phe Lys Glu
500 505 510
Glu Asp Thr Pro Asn Phe Thr Gly Ser Phe Tyr Ser Lys Thr Lys Ala
515 520 525
Met Val Glu Glu Leu Leu Lys Asn Tyr Glu Asn Val Cys Thr Leu Arg
530 535 540
Val Arg Met Pro Ile Ser Ser Asp Leu Thr Asn Pro Arg Asn Phe Ile
545 550 555 560
Thr Lys Ile Ala Arg Tyr Glu Lys Val Val Asp Ile Pro Asn Ser Met
565 570 575
Thr Ile Leu Asp Glu Leu Leu Pro Ile Ser Ile Glu Met Ala Lys Arg
580 585 590
Asn Leu Thr Gly Ile Tyr Asn Phe Thr Asn Pro Gly Val Val Ser His
595 600 605
Asn Glu Ile Leu Glu Met Tyr Arg Asp Tyr Ile Asp Pro Ser Phe Thr
610 615 620
Trp Lys Asn Phe Thr Leu Glu Glu Gln Ala Lys Val Ile Val Ala Pro
625 630 635 640
Arg Ser Asn Asn Glu Leu Asp Ala Thr Lys Leu Lys Thr Glu Phe Pro
645 650 655
Glu Leu Met Ser Ile Lys Glu Ser Leu Ile Lys Phe Val Phe Glu Pro
660 665 670
Asn Lys Lys Thr Glu Val Lys Ala
675 680
<210> 5
<211> 2436
<212> DNA
<213> GmSUS基因(Glycine max)
<400> 5
atggccaccg atcgcttaac ccgcgttcat agtctgcgcg aacgcttaga tgaaaccctg 60
accgccaatc gcaacgagat tctggccctg ctgagtcgga ttgaagccaa aggcaaaggt 120
attcttcaac atcatcaagt tattgcagaa tttgaagaaa ttccggaaga aaatcgtcag 180
aaactgaccg atggtgcctt tggcgaagtg ctccgaagca cccaggaagc cattgtgctg 240
ccgccgtggg ttgccttagc agtgcgcccg cgacccggcg tttgggaata tctgcgcgtt 300
aatgttcatg cactggtggt tgaagaatta cagccggcgg aatatctgca ttttaaagaa 360
gaactggttg atggtagtag taatggcaat tttgtgctgg aactggattt tgaaccgttt 420
aatgcagcct ttccgcgccc gaccctgaac aagtcaattg gcaatggcgt tcagtttctg 480
aatcgtcatc tgagcgccaa actgtttcat gataaagaat cactgcatcc gctgctggaa 540
tttctgcgct tacatagcgt taaaggcaaa accctgatgc tgaatgatcg cattcagaat 600
ccggatgcct tacagcatgt gttacgcaaa gccgaagaat atctgggcac cgttccgccg 660
gaaaccccgt atagcgaatt tgaacataaa tttcaggaaa ttggcttaga acgcggttgg 720
ggtgacaatg ccgaaagggt gctggaatct attcagctgc tgcttgatct gttagaagcc 780
cctgatccgt gtaccttaga aacctttctg ggtcgcattc cgatggtgtt taatgtagtg 840
attctgtctc cgcatggcta ttttgcacag gataatgtgt taggctatcc ggataccggc 900
ggccaggtgg tgtatattct ggatcaggtt cgtgccctgg aaaacgagat gttacatcgc 960
attaaacagc agggcttaga tattgttccg cgcattctga ttattacccg tctgctgccg 1020
gatgcagttg gcaccacctg tggtcagcgc ctggaaaaag tgtttgggac agaacatagt 1080
catattctgc gcgttccgtt tcgtaccgaa aaaggcattg ttaggaagtg gatttctcgc 1140
tttgaagttt ggccgtatct ggaaacctat accgaagatg ttgcacatga actggccaaa 1200
gaattacagg gtaaaccgga tctgattgtg ggcaattata gcgatggtaa tattgttgcc 1260
tctttactgg cccataaact gggcgtgacc cagtgtacca ttgcacatgc cttagaaaaa 1320
accaaatatc cggaaagtga tatatattgg aaaaaactgg aagaacgcta tcatttttct 1380
tgtcagttta ccgctgatct gtttgccatg aatcataccg attttattat tacctcaacc 1440
tttcaggaaa ttgcaggtag caaagatacc gtgggccagt atgaatctca taccgccttt 1500
accctgccgg gtctgtatcg tgtggttcat ggcattgatg tgtttgatcc gaagtttaat 1560
attgtgagtc cgggtgcaga tcagaccata tactttccgc ataccgaaac ctcacgtcgc 1620
ttaaccagct ttcatccgga aattgaagaa ctgctgtata gtagcgtgga aaacgaggaa 1680
catatttgtg tgctgaaaga tcgctctaaa ccgattattt ttacgatggc acgcttagat 1740
cgcgttaaaa atattaccgg cttagtggaa tggtatggga agaatgccaa actgcgcgaa 1800
ctggttaact tagttgtggt tgcaggcgat cgtcgcaaag aatctaaaga cctggaagaa 1860
aaagcagaga tgaagaaaat gtatggtctg attgaaacct ataagctgaa tggtcagttt 1920
cgttggatta gctcacagat gaatcgcgtg cgtaatggcg aactgtatcg cgtgatttgt 1980
gatacccgcg gtgcctttgt tcagccggca gtgtatgaag cctttggtct gaccgttgtg 2040
gaagccatga cctgtggcct gccgaccttt gccacctgta atggcggtcc cgcggaaatt 2100
attgtgcatg ggaaaagcgg ctttcatatt gatccgtatc atggcgatcg tgcagccgat 2160
ctgttagtgg acttctttga aaaatgtaaa ttagatccga cccattggga taaaattagc 2220
aaagcaggct tacagcgcat tgaagaaaaa tatacctggc aaatatatag tcagcgctta 2280
ctgaccctga ccggcgtgta tggcttttgg aaacatgtga gtaacctcga tcgtcgcgaa 2340
tcacgtcgct atctggaaat gttttatgca ctgaaatatc gtaaactggc agaatcagtt 2400
ccgttagcag ccgaacacca tcaccatcac cattaa 2436
<210> 6
<211> 29
<212> DNA
<213> VvRHM-N-1(Artificial Sequence)
<400> 6
catgccatgg caacccatac cccgaaaaa 29
<210> 7
<211> 33
<212> DNA
<213> VvRHM-N-2(Artificial Sequence)
<400> 7
cgcggatccc accggcacaa ccatgcgggt ctg 33
<210> 8
<211> 33
<212> DNA
<213> NRS/ER-1(Artificial Sequence)
<400> 8
cgcggatcca caatggttgc agatgccaat ggt 33
<210> 9
<211> 27
<212> DNA
<213> NRS/ER-2(Artificial Sequence)
<400> 9
ccgctcgagt gctttaactt ctgtctt 27
Claims (5)
1.一种催化制备UDP-鼠李糖的融合酶，其特征在于氨基酸序列如SEQ ID NO. 4所示。
2.编码权利要求1所述融合酶的基因，其特征在于核苷酸序列如SEQ ID NO. 3所示。
3.含有权利要求2所述基因的重组质粒。
4.含有权利要求3所述重组质粒的大肠杆菌。
5.权利要求1所述的融合酶与蔗糖合成酶组成双酶催化体系在制备UDP-鼠李糖中的应用, 反应体系100μL包括：50 mM pH 8.0的磷酸缓冲液，300 mM蔗糖，8 mM UDP，1 mM NAD+，1 mM DTT和0.16 mg/mL 融合酶及0.02 mg/mL 蔗糖合成酶，30℃反应48小时，能获得0.57mM的UDP-鼠李糖。
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