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1、面包酵母生物催化不對(duì)稱(chēng)合成丹參素冰片酯匡新謀1,孫穎2,白亞軍2,南葉飛3,鄭曉暉2*(1寧波職業(yè)技術(shù)學(xué)院化工學(xué)院,浙江寧波,315800;2西北大學(xué)生命科學(xué)學(xué)院,陜西西安,710069;3西安石油大學(xué)化學(xué)化工學(xué)院,陜西西安,710065)摘要:本文以3,4-二羥基苯甲醛為原料,經(jīng)Knoevenagel縮合、水解反應(yīng)合成β-(3,4-二羥基苯基)丙酮酸,利用對(duì)甲基苯磺酸催化β-(3,4-二羥基苯基)丙酮酸和冰片反應(yīng)合成了β-(3,4-二羥基苯基)丙酮酸冰片酯,最后利用面包酵母生物催化不對(duì)稱(chēng)合成了丹參素冰片酯(DBZ)。系統(tǒng)考察了葡萄糖加入量、反應(yīng)時(shí)間、pH及β
2、-環(huán)糊精加入量等因素對(duì)面包酵母生物催化合成不對(duì)稱(chēng)丹參素冰片酯的影響,結(jié)果表明:在底物β-(3,4-二羥基苯基)丙酮酸冰片酯加入量為0.5g時(shí),其最佳反應(yīng)條件為:葡萄糖30g、β-環(huán)糊精1.5g、pH為7、反應(yīng)時(shí)間24h,此條件下對(duì)映體過(guò)量值(ee值)高達(dá)84.9%,產(chǎn)物主要為S構(gòu)型的丹參素冰片酯。該工藝條件溫和、成本較低,是一條極具價(jià)值的丹參素冰片酯生產(chǎn)工藝。關(guān)鍵詞:面包酵母;生物催化;不對(duì)稱(chēng)還原;β-環(huán)糊精;丹參素冰片酯StudyonBiosynthesisofAsymmetricSyntheticDanshensuBorneolesterbyBaker's
3、Yeast(KUANGXin-mou1,SUNYing2,BAIYa-jun2,NANYe-fei3,ZHENGXiao-hui2)(1Schoolofchemicalengineering,NingboNingboPolytechnic,Ningbo315800,ZheJiang,China;2CollegeofLifeSciences,NorthwestUniversity,Xi'an710069,ShanXi,China;3CollegeofChemistryandChemicalEngineering,Xi’anShiyouUniversity,Xi’
4、an710065,ShanXi,China)Abstract:Inviewofthedisadvantagesofhighcost、hashexperimentalconditionsandlowutilizationrateofrawmaterialsinexistingreports.Inthepaper,3,4-dihydroxybenzaldehydewasusedasrawmaterial,refertotheliteraturemethod,andβ-(3,4-dihydroxyphenyl)pyruvateborneolesterwassynth
5、esizedatfirst,thenunderthebread’syeastfermentationliquidandtargetproductDanshensuborneolesterwassynthesized.Theinfluenceofamountofglucoseandβ-cyclodextrin、reactiontime、pHwereinvestigatedinthepaper.Whenβ-(3,4-dihydroxyphenyl)pyruvateborneolesterwas0.5g,Andthebestconditionswereasfollo
6、w:amountofglucosewas30g,reactiontimewas24h,pHwas7,amountofβ-cyclodextrinwas1.5g.enantiomericexcessvalveofthetargetproductashighas84.9%,andmainconfigurationwasS-DBZ.Thereactionconditionsoftheprocessinthispaperweremildandthecostwaslow,whichwasaveryvaluableprocessfortheproductionofDans
7、hensuborneolester.Keyword:Baker'syeast;Biocatalytic;asymmetricreduction;β-(3,4-dihydroxyphenyl)pyruvateborneolester;DanshensuBorneolEster基金項(xiàng)目:1超臨界流體色譜的開(kāi)發(fā)與應(yīng)用(2013YQ170525;子項(xiàng)目:超臨界流體色譜在中藥及其代謝物中的應(yīng)用研究,2013YQ17052509);2中國(guó)長(zhǎng)江學(xué)者課程和教育部大學(xué)創(chuàng)新研究團(tuán)隊(duì)(IRT_15R55)Foundationitem:1The?Development?and?App
8、lication?of?Supercr