LIPASE-CATALYZED REACTIONS OF CHIRAL HYDROXYACID ESTERS - COMPETITION OF ESTERIFICATION AND TRANSESTERIFICATION

被引：20

作者：

ENGEL, KH

BOHNEN, M

DOBE, M

机构：

[1] Technische Universität Berlin, Institut für Biotechnologie, Berlin, Fachgebiet Chemischtechnische Analyse

来源：

ENZYME AND MICROBIAL TECHNOLOGY | 1991年 / 13卷 / 08期

关键词：

LIPASE; ENANTIOSELECTIVITY; HYDROXYACID ESTERS; ESTERIFICATION; TRANSESTERIFICATION;

D O I：

10.1016/0141-0229(91)90080-T

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

Lipase from Candida cylindracea catalyses two reactions between racemic hydroxyacid esters and octanoic acid in heptane: esterification of the hydroxy group, leading to acyloxyacid esters, and transesterification via acidolysis, liberating the free hydroxy acids. The reaction rate and stereochemical course of these pathways are dependent on the structure of the ester substrate. Enantioselective transesterification is the major reaction of ethyl 2-hydroxyhexanoate and leads to products of considerable optical purity. Shifting the position of the hydroxy group in the substrate causes increased esterification and a reversal of the enantioselectivities of the competing pathways. Analogous reactions in aqueous medium confirmed these phenomena.

引用

页码：655 / 660

页数：6

共 28 条

[1] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTION OF ENANTIOMERS .2. ENZYME-CATALYZED ESTERIFICATIONS IN WATER ORGANIC-SOLVENT BIPHASIC SYSTEMS [J].