ENZYMES IN ORGANIC-SYNTHESIS .49. RESOLUTIONS OF RACEMIC MONOCYCLIC ESTERS WITH PIG-LIVER ESTERASE

被引：30

作者：

TOONE, EJ ^{[1
]}

JONES, JB ^{[1
]}

机构：

[1] UNIV TORONTO,DEPT CHEM,80 ST GEORGE ST,TORONTO M5S 1A1,ONTARIO,CANADA

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(00)82360-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Pig liver esterase (PLE)- catalyzed hydrolyses of the racemic methyl esters of cyclobutane-, cyclohexane-, and cyclohex-4-ene-carboxylic acids bearing cis-2-methyl or cis-2-bromomethyl substituents are highly stereoselective, giving the corresponding acid products of greater-than-or-equal-to 97% ee. The stereoselectivity of the enzyme exhibits the expected reversal for such compounds, with the absolute configurations of the cyclobutane and cyclohexane acids being of the opposite absolute configuration types, and cyclopentane substrates such as cis-1-carbomethoxy-2-methylcyclopentane representing the change-over structures and giving products of only 22% ee. This stereoselectivity reversal, and the absolute configurations preferred, are as predicted by the recently proposed active site model for the enzyme.

引用

页码：207 / 222

页数：16

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