3-HYDROXYGLUTARATE AND BETA-EPOXY, GAMMA-EPOXY ESTERS AS SUBSTRATES FOR PIG-LIVER ESTERASE (PLE) AND ALPHA-CHYMOTRYPSIN

被引：49

作者：

MOHR, P ^{[1
]}

ROSSLEIN, L ^{[1
]}

TAMM, C ^{[1
]}

机构：

[1] UNIV BASEL, INST ORGAN CHEM, ST JOHANNS RING 19, CH-4056 BASEL, SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1987年 / 70卷 / 01期

关键词：

D O I：

10.1002/hlca.19870700118

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The pH dependence of the .alpha.-chymotrypsin-catalyzed hydrolysis of dimethyl 3-hydroxyglutarate (3) has been studied. The e.e. was determined by HPLC analysis of diastereoisomeric camphanoic-acid derivatives. Kinetic resolution of the .beta.,.gamma.-epoxy esters 10 and 24 by pig liver esterase has been shown to provide an alternative access to chiral .beta.-hydroxy esters and acids of high optical purity. By this latter method, the unnatural enantiomer of .gamma.-amino-.beta.-hydroxybutyric acid (GABOB) has been synthesized. Finally, dimethyl meso-3,4-epoxyadipate (19) was hydrolyzed by pig liver esterase with almost 100% selectivity.

引用

页码：142 / 152

页数：11

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