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An Unusual ( R )‐Selective Epoxide Hydrolase with High Activity for Facile Preparation of Enantiopure Glycidyl Ethers
Author(s) -
Zhao Jing,
Chu YanYan,
Li AiTao,
Ju Xin,
Kong XuDong,
Pan Jiang,
Tang Yun,
Xu JianHe
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100031
Subject(s) - enantiopure drug , chemistry , epoxide hydrolase , epoxide , biocatalysis , substrate (aquarium) , bacillus megaterium , enantioselective synthesis , ether , organic chemistry , enzyme , stereochemistry , catalysis , reaction mechanism , oceanography , geology , biology , bacteria , genetics , microsome
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.