Selectivity enhancement of enantio- and stereo-complementary epoxide hydrolases and chemo-enzymatic deracemization of (±)-2-methylglycidyl benzyl ether

被引：32

作者：

Simeó, Y ^{[1
]}

Faber, K ^{[1
]}

机构：

[1] Graz Univ, Dept Chem Organ & Bioorgan Chem, A-8010 Graz, Austria

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 03期

关键词：

D O I：

10.1016/j.tetasy.2005.12.018

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The kinetic resolution of (+/-)-2-methylglycidyl benzyl ether was achieved via enantioselectivc biohydrolysis using microbial and plant epoxide hydrolases. Depending on the type of enzyme, opposite enantiopreference and stereo-complementary mode of action (i.e., retention vs inversion of configuration) led to hetero- and homochiral product mixtures. optimization of the reaction conditions for Rhodococcus sp. R312 led to significantly enhanced enantioselectivity (E > 200), which enabled the deracemization of (+/-)-2-methylglycidyl benzyl ether via biohydrolysis (proceeding with retention of configuration) followed by inverting acid-catalyzed hydrolysis to furnish (R)-1-benzyloxy-2-methylpropane-2,3-diol in > 97% ee and 78% yield from the racemate. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：402 / 409

页数：8

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