A Chemo-enzymatic Route for the Preparation of Chiral （S）-3-Hydroxy-3-phenylpropanoic Acid

作     者：ZHAO Ying MA Haiping FU Zhijing ZHANG Guoyan 

作者机构：College of Chemistry Jilin University Changchun 130012 P. R. China 

出 版 物：《Chemical Research in Chinese Universities》 (高等学校化学研究（英文版）)

年 卷 期：2014年第30卷第6期

页      面：915-918页

核心收录：

学科分类：0710[理学-生物学] 081702[工学-化学工艺] 07[理学] 08[工学] 0817[工学-化学工程与技术] 09[农学] 071007[理学-遗传学] 0901[农学-作物学] 0836[工学-生物工程] 090102[农学-作物遗传育种] 

基　　金：Supported by the Graduate Training Program Foundation of Jilin University  China 

主　　题：Optically active β-hydroxy acid Porcine pancreas lipase(PPL) Chemo-enzymatic process 

摘      要：（S）-3-Hydroxy-3-phenylpropanoic acid is a potential progenitor of optically pure tomoxetine hydrochlo- ride and fluoxetine hydrochloride which are currently available antidepressant drugs. We report here the chemical synthesis of racemic substrate （R,S）-ethyl 3-hydroxy-3-phenylpropanoate and enzymatic preparation of S-isomer of the substrate by employing Porcine pancreas lipase（PPL） as a biocatalyst. Optimum enzyme-catalyzed reaction con- ditions, such as the effects of the temperature, pH and solvents on conversion degree and enantiomeric excess, were studied. An optimal temperature of 35 ℃ and pH=7.5 are the best for the resolution of （R,S）-ethyl 3-hydroxy-3- pheylpropanoate by PPL when 0.1 mol/L phosphate buffer solution acts as a medium. This work provides a practi- cally chemo-enzvmatic oreoaration of chiral β-hvdroxv acid by PPL.