CN111676251A - 一种咖啡酸和香兰素的制备方法及其反应催化剂的制备方法 - Google Patents
一种咖啡酸和香兰素的制备方法及其反应催化剂的制备方法 Download PDFInfo
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Abstract
本发明公开了一种咖啡酸和香兰素的生物制造方法,第一步以葡萄糖等为起始原料,通过大肠杆菌菌种,发酵生产中间体3‑脱氢莽草酸,中间体的浓度大于50g/L,糖质量转化率(A/G)为30‑40%,可达到最大的理论转化率;第二步采用酶催化过程,通过自主开发合适的酶,以发酵过程获得的3‑脱氢莽草酸为原料,生物酶催化得到中间体原儿茶酸;第三步采用酶催化过程,通过自主开发合适的酶,以前一步获得的原儿茶酸为原料,生物酶催化得到中间体咖啡酸;第四步采用酶催化过程,通过自主开发合适的酶,以前一步获得的咖啡酸为原料,生物酶催化得到产品香兰素。整个过程采用一步发酵加三步生物酶催化,合成产品香兰素。本发明的有益效果:以葡萄糖为原料,其价格实惠,来源广泛,而且整个工艺得到了简化,产物浓度高,可达到20‑80g/L,降低香兰素的生产成本且减少环境污染;本路线副反应少,后处理简便,总收率高,可达25%;反应时间短,全部过程在72‑96h内完成。
Description
技术领域
本发明涉及使用酶催化的方法来制取芳环化合物衍生物的技术,具体而言,涉及生物法生产香兰素的工艺。
背景技术
香兰素俗称香草粉、香草醛、云尼拿粉、香草精、香荚兰素等。从芸香科植物香荚兰豆中提取。白色至微黄色结晶或结晶状粉末,微甜。溶于热水、甘油和酒精,在冷水及植物油中不易溶解。香气稳定,在较高温度下不易挥发。在空气中易氧化,遇碱性物质易变色。
化学名称为3-甲氧基-4-羟基苯甲醛,具有香荚兰豆香气及浓郁的奶香,起增香和定香作用,广泛用于化妆品、烟草、糕点、糖果以及烘烤食品等行业,是全球产量最大的合成香料品种之一,工业化生产香兰素已有 100多年的历史。香兰素也可用作植物生长促进剂、杀菌剂、润滑油消泡剂等,还是合成药物和其他香料的重要中间体。除此之外,它还可在电镀工业中用作上光剂,农业中用作催熟剂,橡胶制品中用作除臭剂,塑料制品中用作抗硬化剂和作为医药中间体使用等,应用十分广泛。
目前,香兰素的生产工艺主要有两种:
化学合成法:主要路线为愈创木酚-乙醛酸合成法,见下路线,为反应式1:
愈创木酚-乙醛酸化学合成香兰素的路线
以愈创木酚和乙醛酸为原料,通过强碱为催化剂进行缩合反应,然后经过氧化和酸化水解等一系列化工过程制得产品。此工艺操作简单,但是由于强酸强碱对环境污染大、原料来源受限,原料愈创木酚(大于4万/吨)和乙醛酸(大于2万/吨)的成本较高。
生物合成天然香兰素:采用天然产物做为来源合成香兰素的方法众多,以原料来源区分主要有香兰荚、米糠等提取的阿魏酸、丁香提取的丁香酚、姜黄和玉米淀粉糖等。其中香兰荚来源制备的香兰素较贵,米糠等提取的阿魏酸制备的香兰素属于中等价位,采用后三种原料来源进行大规模生产香兰素的报道还比较少,美国国际香精香料(IFF)在2014年开始从玉米糖开始直接发酵获得香兰素,并将以“natural vanillin”的标示进入市场,但采用直接从玉米糖发酵获得的产物浓度很低,只有0.5-1g/L,其生产所用原料糖和后提取浓缩的成本都会很高。
据文献报道:欧洲(European Directive 88/388/CEE, JO No. L184, 22 June1988)和美国的法规规定微生物转化阿魏酸产生的香兰素是属于天然产品,但欧洲的法规会更严格一些,例如玉米芯采用碱水解这种化学方法获得的阿魏酸,在欧洲法规中认为不是天然的,而美国法规仍认为是天然的。所以要制备天然来源的香兰素,如要进入欧洲市场,应尽量避免化学处理过程。
以上两种香兰素的制备方法中,各有不足,化学合成法对环境污染大,难以进入欧洲市场。生物合成法利用植物资源为原料,成本较高。
发明内容
为了解决上述问题,本发明提供了一种咖啡酸和香兰素的制备方法及其反应催化剂的制备方法,具体技术方案如下:
一种邻甲基转移酶催化剂和芳香族羧酸还原酶的制备方法,具体步骤如下:
步骤一:将邻甲基转移酶(o-methyltransferase,OMT)片段或芳香族羧酸还原酶(ACAR)片段分别重组到pET21a载体上,阳性重组质粒-pET21a(+)转化表达宿主菌BL21(DE3),得到原核表达菌株pET21a(+)/ BL21(DE3);
步骤二:将上述表达菌株在加有终浓度为100ug/mL氨苄青霉素的5mL LB液体培养基中于37℃、200rpm振荡培养过夜后,按1%(V/V)比例接种于含有终浓度为100ug/mL氨苄青霉素的500mL LB液体培养基中,于37℃、200rpm振荡培养。待OD600在0.8-1.0之间时,加入终浓度为0.1mM的诱导剂IPTG(异丙基-β-D-硫代半乳糖苷,IPTG),并在25℃诱导过夜;
步骤三:将步骤二所得液在8000rpm条件下离心收集,然后悬浮于50mM pH7.0 磷酸钠缓冲液中,超声破碎(200W,3s/5s,10min),4℃,8000rpm离心20min,得到邻甲基转移酶催化剂(OMT)或芳香族羧酸还原酶催化剂(ACAR)。
优选地,其特征在于:所述步骤二中的培养基包括:10g/L 胰蛋白胨(OXIOD),5g/L酵母粉(OXIOD),10g/L 氯化钠(国药试剂)。
本发明中,邻甲基转移酶来源于人源(Homo sapiens),芳香族羧酸还原酶来源于大肠杆菌(E.coli)或酵母(Yeast)。
该酶作为催化剂的形态可以是:纯酶、相应的重组菌休止细胞、粗酶液或者粗酶粉等。
一种制备咖啡酸的方法,具体步骤如下:
步骤一:将葡萄糖发酵得到3-脱氢莽草酸,进而使用3-脱氢莽草酸脱水酶催化剂(中国专利申请号:2019104520898)催化得到原儿茶酸。
步骤二:将步骤一得到的原儿茶酸溶解并加入磷酸盐,调整PH到6-11,加入权利要求1中的邻甲基转移酶催化剂和辅助因子S-腺苷甲硫氨酸(SAM);
步骤三:将步骤二中的反应体系在25-40℃下恒温搅拌,反应16-24小时,得到咖啡酸。
优选地,其特征在于:所述步骤二中加入磷酸盐至最终浓度为50mM。
咖啡酸是以原儿茶酸(PCA)为原料,使用邻甲基转移酶催化剂(OMT)进行的生物催化反应,反应方程式为:
反应体系为:邻甲基转移酶催化剂(OMT),磷酸缓冲液,原儿茶酸,辅助因子S-腺苷甲硫氨酸(SAM),氯化钠。具体的为:酶的用量在1-10g/L,缓冲液浓度在50-200mM,缓冲液pH值在6.0-11之间,氯化钠浓度在10-100mmol之间,底物浓度在20-80g/L之间。反应后产物通过乙腈淬灭后经高效液相色谱(HPLC)验证,反应转化率可达80%,90%,或95%,或99%以上,产物的纯度值可达90%,或95%,或99%以上。
一种香兰素的制备方法,具体步骤如下:
步骤一:取权利要求1中所得的咖啡酸溶解于磷酸盐的水溶液中,调节pH到6-11;
步骤二:向步骤一的体系中加入权利要求1中的芳香族羧酸还原酶催化剂(ACAR)和辅助因子NAD;
步骤三:将步骤二中的反应体系在25-40℃下恒温搅拌,反应16-24小时,得到香兰素。
优选地,其特征在于:所述步骤一中磷酸盐浓度为50mM。
香兰素在咖啡酸的基础上,采用芳香族羧酸还原酶催化剂(ACAR)进行的生物催化反应,反应方程式为:
反应体系为:芳香族羧酸还原酶催化剂(ACAR),磷酸缓冲液,咖啡酸,NAD或者NADP之类的辅助因子。具体的为:酶的用量在1-10g/L,缓冲液浓度在50-200mM,缓冲液pH值在6.0-11之间,底物浓度在20-80g/L之间。反应后产物通过乙腈淬灭后经高效液相色谱(HPLC)验证,反应转化率可达90%,或95%,或99%以上,产物的纯度值可达90%,或95%,或99%以上。
本发明中使用以葡萄糖为原料发酵得到的3-脱氢莽草酸为底物,经过酶催化生成原儿茶酸,再经过酶催化可以得到咖啡酸,进一步酶催化得到香兰素,解决了已有方法中原料来源问题,同时显著简化工艺,减少环境污染,降低香兰素的生产成本。
附图说明
图1为实施例3/4中由3-脱氢莽草酸催化生成原儿茶酸的HPLC检测图;
图2为实施例5/6/7中原儿茶酸催化生成咖啡酸的HPLC检测图;
图3为实施例8/9/10/11中咖啡酸催化生成香兰素的HPLC检测图;
具体实施方式
为了加深对本发明的理解,下面将结合实施例对本发明做进一步详细描述,该实施例仅用于解释本发明,并不对保护范围构成限定。
实施例1 原核表达体系的构建
邻甲基转移酶(OMT)基因片段由南京金斯瑞生物科技有限公司合成,并重组到pET21a载体上。将阳性重组质粒pET21a(+)转化表达宿主菌BL21(DE3)(购自天根生化科技(北京)有限公司),得到原核表达菌株OMT-pET21a(+)/ BL21(DE3),作为后续催化反应原代菌株。
芳香族羧酸还原酶(ACAR)基因片段由南京金斯瑞生物科技有限公司合成,并重组到pET21a载体上。将阳性重组质粒pET21a(+)转化表达宿主菌BL21(DE3)(购自天根生化科技(北京)有限公司),得到原核表达菌株ACAR-pET21a(+)/ BL21(DE3),作为后续催化反应原代菌株。
实施例2 酶的发酵制备
上述构建的表达菌株OMT-pET21a(+)/ BL21(DE3)、ACAR-pET21a(+)/ BL21(DE3)在加有终浓度为100ug/mL氨苄青霉素的5mL LB液体培养基【10g/L 胰蛋白胨(OXIOD),5g/L 酵母粉(OXIOD),10g/L 氯化钠(国药试剂)】中于37℃、200rpm振荡培养过夜后,按1%(V/V)比例接种于含有终浓度为100ug/mL氨苄青霉素的500mL LB液体培养基中,于37℃、200rpm振荡培养。待OD600在0.8-1.0之间时,加入终浓度为0.1mM的诱导剂IPTG(异丙基-β-D-硫代半乳糖苷,IPTG),并在25℃诱导过夜。菌体在8000rpm条件下离心收集,然后悬浮于50mMpH7.0 磷酸钠缓冲液中,超声破碎(200W,3s/5s,10min),4℃,8000rpm离心20min,取上清备用。
实施例3
在含有50g3-脱氢莽草酸的800ml水溶液中加入磷酸盐至终浓度为50mM,溶液pH值达到7.0,待搅拌溶解后加入3-脱氢莽草酸脱水酶酶液200mL使得终体积为1L。反应液置于37℃恒温水浴锅中,机械搅拌反应。反应1h后进行HPLC检测,底物转化率>98%,见图1。
实施例4
在含有60g3-脱氢莽草酸的800ml水溶液中加入磷酸盐至终浓度为50mM,溶液pH值达到7.0,待搅拌溶解后加入3-脱氢莽草酸脱水酶酶液200mL使得终体积为1L。反应液置于37℃恒温水浴锅中,机械搅拌反应。反应1.5h后进行HPLC检测,底物转化率>98%,见图1。
实施例5
在含有50g原儿茶酸的800ml反应溶液中加入磷酸盐至终浓度为50mM,溶液pH值达到7.0,待搅拌溶解后加入邻甲基转移酶酶液200ml,辅助因子S-腺苷甲硫氨酸(SAM)0.1g,使得终体积为1L。反应液置于37℃恒温水浴锅中,搅拌反应。反应16h后进行HPLC检测,底物转化率>98%。
实施例6
在含有80g原儿茶酸的800ml反应溶液中加入磷酸盐至终浓度为50mM,溶液pH值达到7.0,待搅拌溶解后加入邻甲基转移酶酶液200ml,辅助因子S-腺苷甲硫氨酸(SAM)0.1g,使得终体积为1L。反应液置于37℃恒温水浴锅中,搅拌反应。反应16h后进行HPLC检测,底物转化率>95%。
实施例7
在含有80g原儿茶酸的800m水溶液中加入磷酸盐至终浓度为50mM,溶液pH值达到6.0,待搅拌溶解后加入邻甲基转移酶酶液200ml,辅助因子S-腺苷甲硫氨酸(SAM)0.1g,使得终体积为1L。反应液置于37℃恒温水浴锅中,搅拌反应。反应16h后进行HPLC检测,底物转化率>95%。
实施例8
将20g咖啡酸溶解于800mL磷酸盐浓度为50mM的水溶液终,调节pH至7.0,待搅拌溶解后加入芳香族羧酸还原酶酶液200ml,辅助因子NAD 0.2g,反应终体积为1L。反应液置于37℃恒温水浴锅中,搅拌反应。反应24h后进行HPLC检测,底物转化率>98%。
实施例9
将50g咖啡酸溶解于800mL磷酸盐浓度为50mM的水溶液终,调节pH至7.0,待搅拌溶解后加入芳香族羧酸还原酶酶液200ml,辅助因子NAD 0.2g,反应终体积为1L。反应液置于37℃恒温水浴锅中,机械搅拌反应。反应24h后进行HPLC检测,底物转化率>98%。
实施例10
将60g咖啡酸溶解于800mL磷酸盐浓度为50mM的水溶液终,调节pH至6.0,待搅拌溶解后加入芳香族羧酸还原酶酶液200ml,辅助因子NAD 0.2g,反应终体积为1L。反应液置于37℃恒温水浴锅中,搅拌反应。反应24h后进行HPLC检测,底物转化率>98%。
实施例11
将80g咖啡酸溶解于800mL磷酸盐浓度为50mM的水溶液终,调节pH至7.0,待搅拌溶解后加入芳香族羧酸还原酶酶液200ml,辅助因子NAD 0.2g,反应终体积为1L。反应液置于30℃恒温水浴锅中,搅拌反应。反应24h后进行HPLC检测,底物转化率>98%。
实施例12 HPLC检测方法建立
底物转化率的检测通过HPLC进行,检测的条件如下:仪器为安捷伦HPLC1100、液相柱为安捷伦Agllent 5 TC-C18(2) 250*4.6mm、流动相Buffer A为纯度大于99%的甲醇溶液、流动相Buffer B为0.1%的磷酸水溶液、A相和B相以一定梯度混合,柱温箱温度25°C、流速1mL/min、检测波长254nm、样品浓度2mg/mL、进样量10uL。检测后将产物的峰面积除以产物和底物的峰面积之和,求得转化率。
上述检测样品均采用流动相稀释到合适浓度后,用0.22μm的滤膜过滤进仪器检测。
以上实施例中,未注明具体条件的实验方法,通常按常规条件,如《分子克隆实验指南》(J.萨姆布鲁克,D.W.拉塞尔著,黄培堂,汪嘉玺,朱厚础等译,第三版,北京:科学出版社,2002)中所述的方法进行。
本实施例中涉及一种功能性邻甲基转移酶(简写为OMT),能够进行催化原儿茶酸合成咖啡酸,其氨基酸序列衍生自,且具有附件所列的序列。本发明还涉及一种功能性芳香族羧酸还原酶(简写ACAR),能够催化咖啡酸合成香兰素,其氨基酸序列衍生自人源,且具有附件所列的序列。
综合上述实施例可知,制得酶之后,再进行构建,形成有催化效果的催化剂,可以用于生物反应中,给香兰素的制备提供了一条新的路线,以容易获得的葡萄糖为原料发酵得到的3-脱氢莽草酸为底物,经过酶催化生成原儿茶酸,再经过酶催化可以得到咖啡酸,进一步酶催化可以得到香兰素,解决了已有方法中原料来源问题,同时显著简化工艺,减少环境污染,降低香兰素生产成本。
序列表
<110> 上海仁酶生物科技有限公司
南京趣酶生物科技有限公司
<120> 一种咖啡酸和香兰素的制备方法及其反应催化剂的制备方法
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Ala Thr Trp Gln Arg Leu Ala Glu Thr Val Asp Leu Ile Val His Pro
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Ala Ala Leu Val Asn His Val Leu Pro Tyr Thr Gln Leu Phe Gly Pro
885 890 895
Asn Val Val Gly Thr Ala Glu Ile Val Arg Leu Ala Ile Thr Ala Arg
900 905 910
Arg Lys Pro Val Thr Tyr Leu Ser Thr Val Gly Val Ala Asp Gln Val
915 920 925
Asp Pro Ala Glu Tyr Gln Glu Asp Ser Asp Val Arg Glu Met Ser Ala
930 935 940
Val Arg Val Val Arg Glu Ser Tyr Ala Asn Gly Tyr Gly Asn Ser Lys
945 950 955 960
Trp Ala Gly Glu Val Leu Leu Arg Glu Ala His Asp Leu Cys Gly Leu
965 970 975
Pro Val Ala Val Phe Arg Ser Asp Met Ile Leu Ala His Ser Arg Tyr
980 985 990
Ala Gly Gln Leu Asn Val Gln Asp Val Phe Thr Arg Leu Ile Leu Ser
995 1000 1005
Leu Val Ala Thr Gly Ile Ala Pro Tyr Ser Phe Tyr Arg Thr Asp Ala
1010 1015 1020
Asp Gly Asn Arg Gln Arg Ala His Tyr Asp Gly Leu Pro Ala Asp Phe
1025 1030 1035 1040
Thr Ala Ala Ala Ile Thr Ala Leu Gly Ile Gln Ala Thr Glu Gly Phe
1045 1050 1055
Arg Thr Tyr Asp Val Leu Asn Pro Tyr Asp Asp Gly Ile Ser Leu Asp
1060 1065 1070
Glu Phe Val Asp Trp Leu Val Glu Ser Gly His Pro Ile Gln Arg Ile
1075 1080 1085
Thr Asp Tyr Ser Asp Trp Phe His Arg Phe Glu Thr Ala Ile Arg Ala
1090 1095 1100
Leu Pro Glu Lys Gln Arg Gln Ala Ser Val Leu Pro Leu Leu Asp Ala
1105 1110 1115 1120
Tyr Arg Asn Pro Cys Pro Ala Val Arg Gly Ala Ile Leu Pro Ala Lys
1125 1130 1135
Glu Phe Gln Ala Ala Val Gln Thr Ala Lys Ile Gly Pro Glu Gln Asp
1140 1145 1150
Ile Pro His Leu Ser Ala Pro Leu Ile Asp Lys Tyr Val Ser Asp Leu
1155 1160 1165
Glu Leu Leu Gln Leu Leu
1170
Claims (5)
1.一种制备咖啡酸的方法,具体步骤如下:
步骤一:通过发酵方法获得3-脱氢莽草酸原料的方法,即采用天然来源糖进行微生物合成该原料的过程;
步骤二:将葡萄糖发酵得到3-脱氢莽草酸,进而使用3-脱氢莽草酸脱水酶催化剂催化得到原儿茶酸;
步骤三:将步骤二得到的原儿茶酸溶解并加入磷酸盐,调整pH到6-11,加入邻甲基转移酶催化剂(OMT)和辅助因子S-腺苷甲硫氨酸(SAM);
步骤四:将步骤三中的反应体系在25-40℃下恒温搅拌,反应16-24小时,得到咖啡酸。
2.一种香兰素的制备方法,具体步骤如下:
步骤一:通过发酵方法获得3-脱氢莽草酸原料的方法,即采用天然来源糖进行微生物合成该原料的过程;
步骤二:将葡萄糖发酵得到3-脱氢莽草酸,进而使用3-脱氢莽草酸脱水酶催化剂催化得到原儿茶酸;
步骤三:向步骤二的反应体系中加入邻甲基转移酶催化剂(OMT)和辅助因子SAMS-腺苷甲硫氨酸,催化得到咖啡酸体系液;
步骤四:将步骤三的反应体系中加入芳香族羧酸还原酶催化剂(ACAR)和辅助因子NAD,在25-40℃下恒温搅拌,反应16-24小时,催化得到香兰素。
3.权利要求1中邻甲基转移酶催化剂的制备方法,具体步骤如下:
步骤一:将邻甲基转移酶(o-methyltransferase,OMT)片段重组到pET21a载体上,阳性重组质粒-pET21a(+)转化表达宿主菌BL21(DE3),得到原核表达菌株pET21a(+)/ BL21(DE3);
步骤二:将上述表达菌株在加有终浓度为100ug/mL氨苄青霉素的5mL LB液体培养基中于37℃、200rpm振荡培养过夜后,按1%(V/V)比例接种于含有终浓度为100ug/mL氨苄青霉素的500mL LB液体培养基中,于37℃、200rpm振荡培养,待OD600在0.8-1.0之间时,加入终浓度为0.1mM的诱导剂IPTG(异丙基-β-D-硫代半乳糖苷,IPTG),并在25℃诱导过夜;
步骤三:将步骤二所得液在8000rpm条件下离心收集,然后悬浮于50mM pH7.0 磷酸钠缓冲液中,超声破碎(200W,3s/5s,10min),4℃,8000rpm离心20min,得到邻甲基转移酶催化剂(OMT)。
4.根据权利要求3所述的邻甲基转移酶催化剂的制备方法,其特征在于:所述步骤二中的培养基包括:10g/L 胰蛋白胨(OXIOD),5g/L 酵母粉(OXIOD),10g/L 氯化钠(国药试剂)。
5.权利要求2中芳香族羧酸还原酶催化剂(ACAR)的制备方法,具体步骤如下:
步骤一:将芳香族羧酸还原酶(ACAR)分别重组到pET21a载体上,阳性重组质粒-pET21a(+)转化表达宿主菌BL21(DE3),得到原核表达菌株pET21a(+)/ BL21(DE3);
步骤二:将上述表达菌株在加有终浓度为100ug/mL氨苄青霉素的5mL LB液体培养基中于37℃、200rpm振荡培养过夜后,按1%(V/V)比例接种于含有终浓度为100ug/mL氨苄青霉素的500mL LB液体培养基中,于37℃、200rpm振荡培养,待OD600在0.8-1.0之间时,加入终浓度为0.1mM的诱导剂IPTG(异丙基-β-D-硫代半乳糖苷,IPTG),并在25℃诱导过夜;
步骤三:将步骤二所得液在8000rpm条件下离心收集,然后悬浮于50mM pH7.0 磷酸钠缓冲液中,超声破碎(200W,3s/5s,10min),4℃,8000rpm离心20min,得到芳香族羧酸还原酶催化剂(ACAR)。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114561432A (zh) * | 2020-11-27 | 2022-05-31 | 中国科学院天津工业生物技术研究所 | 一种芳香族化合物的开环方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015121379A2 (en) * | 2014-02-12 | 2015-08-20 | Evolva Sa | Methods of improving production of vanillin |
CN106574269A (zh) * | 2014-06-18 | 2017-04-19 | 罗地亚经营管理公司 | 重组单细胞宿主中香草素产生的改良的选择性 |
CN108570464A (zh) * | 2011-08-08 | 2018-09-25 | 国际香料香精公司 | 用于香草醛或香草醛β-D-葡萄糖苷的生物合成的组合物和方法 |
CN108929886A (zh) * | 2017-05-22 | 2018-12-04 | 味之素株式会社 | 生产目标物质的方法 |
CN110184288A (zh) * | 2019-05-28 | 2019-08-30 | 南京趣酶生物科技有限公司 | 没食子酸和原儿茶酸的制备方法及其反应催化剂的制备方法 |
-
2019
- 2019-12-31 CN CN201911416616.6A patent/CN111676251A/zh active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108570464A (zh) * | 2011-08-08 | 2018-09-25 | 国际香料香精公司 | 用于香草醛或香草醛β-D-葡萄糖苷的生物合成的组合物和方法 |
WO2015121379A2 (en) * | 2014-02-12 | 2015-08-20 | Evolva Sa | Methods of improving production of vanillin |
CN106574269A (zh) * | 2014-06-18 | 2017-04-19 | 罗地亚经营管理公司 | 重组单细胞宿主中香草素产生的改良的选择性 |
CN108929886A (zh) * | 2017-05-22 | 2018-12-04 | 味之素株式会社 | 生产目标物质的方法 |
CN110184288A (zh) * | 2019-05-28 | 2019-08-30 | 南京趣酶生物科技有限公司 | 没食子酸和原儿茶酸的制备方法及其反应催化剂的制备方法 |
Non-Patent Citations (6)
Title |
---|
ESBEN H. HANSEN等: "De Novo Biosynthesis of Vanillin in Fission Yeast (Schizosaccharomyces pombe) and Baker"s Yeast (Saccharomyces cerevisiae)", 《APPLIED AND ENVIRONMENTAL MICROBIOLOGY》 * |
H. PRIEFERT等: "Biotechnological production of vanillin", 《APPLIED MICROBIOLOGY AND BIOTECHNOLOGY》 * |
KAI LI AND J. W. FROST: "Synthesis of vanillin from glucose", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
李强,夏晓晖: "《新编常用中药有效成分手册》", 31 January 2008, 中国协和医科大学出版社 * |
罗诚浩等: "微生物转化法生产香兰素的研究进展", 《化学与生物工程》 * |
赵建芬等: "香兰素的生物合成", 《现代食品科技》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114561432A (zh) * | 2020-11-27 | 2022-05-31 | 中国科学院天津工业生物技术研究所 | 一种芳香族化合物的开环方法 |
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