title: Bioresolution production of (2R,3S)-ethyl-3-phenylglycidate for chemoenzymatic synthesis of the taxol C-13 side chain by Galactomyces geotrichum ZJUTZQ200, a new epoxide-hydrolase-producing strain.
abstract: A newly isolated Galactomyces geotrichum ZJUTZQ200 strain containing an epoxide hydrolase was used to resolve racemic ethyl 3-phenylglycidate (rac-EPG) for producing (2R,3S)-ethyl-3-phenylglycidate ((2R,3S)-EPG). G. geotrichum ZJUTZQ200 was verified to be able to afford high enantioselectivity in whole cell catalyzed synthesis of this chiral phenylglycidate synthon. After the optimization of the enzymatic production and bioresolution conditions, (2R,3S)-EPG was afforded with high enantioselectivity (e.e.S > 99%, E > 49) after a 8 h reaction. The co-solvents, pH buffer solutions and substrate/cell ratio were found to have significant influences on the bioresolution properties of G. geotrichum ZJUTZQ200. Based on the bioresolution product (2R,3S)-EPG, taxol's side chain ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropionate was successfully synthesized by a chemoenzymatic route with high enantioselectivity (e.e.S > 95%).
authors.affiliation: College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310014, China. springweispring@163.com.
authors.forename: Chun
authors.initials: C
authors.lastname: Wei
authors.affiliation: College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310014, China. jor_ling@163.com.
authors.forename: Jinlong
authors.initials: J
authors.lastname: Ling
authors.affiliation: College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310014, China. shenhonglei-77@163.com.
authors.forename: Honglei
authors.initials: H
authors.lastname: Shen
authors.affiliation: College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310014, China. zhuq@zjut.edu.cn.
authors.forename: Qing
authors.initials: Q
authors.lastname: Zhu
mesh_terms: D004851:Epoxide Hydrolases / Q000378:metabolism; D004852:Epoxy Compounds / Q000378:metabolism*; D005848:Geotrichum / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; C043180:ethyl 3-phenylglycidate; D004851:Epoxide Hydrolases