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1、面包酵母生物催化不对称合成丹参素冰片酯匡新谋1,孙颖2,白亚军2,南叶飞3,郑晓晖2*(1宁波职业技术学院化工学院,浙江宁波,315800;2西北大学生命科学学院,陕西西安,710069;3西安石油大学化学化工学院,陕西西安,710065)摘要:本文以3,4-二羟基苯甲醛为原料,经Knoevenagel缩合、水解反应合成β-(3,4-二羟基苯基)丙酮酸,利用对甲基苯磺酸催化β-(3,4-二羟基苯基)丙酮酸和冰片反应合成了β-(3,4-二羟基苯基)丙酮酸冰片酯,最后利用面包酵母生物催化不对称合成了丹参素冰片
2、酯(DBZ)。系统考察了葡萄糖加入量、反应时间、pH及β-环糊精加入量等因素对面包酵母生物催化合成不对称丹参素冰片酯的影响,结果表明:在底物β-(3,4-二羟基苯基)丙酮酸冰片酯加入量为0.5g时,其最佳反应条件为:葡萄糖30g、β-环糊精1.5g、pH为7、反应时间24h,此条件下对映体过量值(ee值)高达84.9%,产物主要为S构型的丹参素冰片酯。该工艺条件温和、成本较低,是一条极具价值的丹参素冰片酯生产工艺。关键词:面包酵母;生物催化;不对称还原;β-环糊精;丹参素冰片酯StudyonBiosynt
3、hesisofAsymmetricSyntheticDanshensuBorneolesterbyBaker'sYeast(KUANGXin-mou1,SUNYing2,BAIYa-jun2,NANYe-fei3,ZHENGXiao-hui2)(1Schoolofchemicalengineering,NingboNingboPolytechnic,Ningbo315800,ZheJiang,China;2CollegeofLifeSciences,NorthwestUniversity,Xi'an710
4、069,ShanXi,China;3CollegeofChemistryandChemicalEngineering,Xi’anShiyouUniversity,Xi’an710065,ShanXi,China)Abstract:Inviewofthedisadvantagesofhighcost、hashexperimentalconditionsandlowutilizationrateofrawmaterialsinexistingreports.Inthepaper,3,4-dihydroxybe
5、nzaldehydewasusedasrawmaterial,refertotheliteraturemethod,andβ-(3,4-dihydroxyphenyl)pyruvateborneolesterwassynthesizedatfirst,thenunderthebread’syeastfermentationliquidandtargetproductDanshensuborneolesterwassynthesized.Theinfluenceofamountofglucoseandβ-c
6、yclodextrin、reactiontime、pHwereinvestigatedinthepaper.Whenβ-(3,4-dihydroxyphenyl)pyruvateborneolesterwas0.5g,Andthebestconditionswereasfollow:amountofglucosewas30g,reactiontimewas24h,pHwas7,amountofβ-cyclodextrinwas1.5g.enantiomericexcessvalveofthetargetp
7、roductashighas84.9%,andmainconfigurationwasS-DBZ.Thereactionconditionsoftheprocessinthispaperweremildandthecostwaslow,whichwasaveryvaluableprocessfortheproductionofDanshensuborneolester.Keyword:Baker'syeast;Biocatalytic;asymmetricreduction;β-(3,4-dihydrox
8、yphenyl)pyruvateborneolester;DanshensuBorneolEster基金项目:1超临界流体色谱的开发与应用(2013YQ170525;子项目:超临界流体色谱在中药及其代谢物中的应用研究,2013YQ17052509);2中国长江学者课程和教育部大学创新研究团队(IRT_15R55)Foundationitem:1The Development and Application of Supercr