文献类型：期刊文献

英文题名：An Unusual (R)-Selective Epoxide Hydrolase with High Activity for Facile Preparation of Enantiopure Glycidyl Ethers

作者：Zhao, Jing[2];Chu, Yan-Yan[1];Li, Ai-Tao[2];Ju, Xin[2];Kong, Xu-Dong[2];Pan, Jiang[2];Tang, Yun[1];Xu, Jian-He[2]

机构：[1]E China Univ Sci & Technol, Dept Pharmaceut Sci, Sch Pharm, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Lab Biocatalysis & Synthet Biotechnol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China

年份：2011

卷号：353

期号：9

起止页码：1510

外文期刊名：ADVANCED SYNTHESIS & CATALYSIS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000292848200021)，CCR-EXPANDED(收录号:WOS:000292848200021)】；

基金：This work was financially supported by the National Natural Science Foundation of China (Nos. 20902023 and 31071604), Ministry of Science and Technology, PR. China (2011CB710800 and 2009ZX09501-016), and China National Special Fund for State Key Laboratory of Bioreactor Engineering (No. 2060204). Cordial thanks are also given to Prof Dr. Manfred T Reetz at Max-Planck-Institut fur Kohlenforschung for his constructive discussion, and to Dr. Jie Sun at ECUST for her valuable suggestions in the manuscript preparation.

语种：英文

外文关键词：enantioselectivity; epoxide hydrolase; glycidyl ethers; kinetic resolution; molecular modeling

摘要：A novel epoxide hydrolase (BMEH) with unusual (R)-enantioselectivity and very high activity was cloned from Bacillus megaterium ECU1001. Highest enantioselectivities (E > 200) were achieved in the bioresolution of ortho-substituted phenyl glycidyl ethers and para-nitrostyrene oxide. Worthy of note is that the substrate structure remarkably affected the enantioselectivities of the enzyme, as a reversed (S)-enantiopreference was unexpectedly observed for the ortho-nitrophenyl glycidyl ether. As a proof-of-concept, five enantiopure epoxides (> 99% ee) were obtained in high yields, and a gram-scale preparation of (S)-ortho-methylphenyl glycidyl ether was then successfully performed within a few hours, indicating that BMEH is an attractive biocatalyst for the efficient preparation of optically active epoxides.