LIPASE-CATALYZED ENANTIOSELECTIVE ACYLATION OF ALCOHOLS - A PREDICTIVE ACTIVE-SITE MODEL FOR LIPASE YS TO IDENTIFY WHICH ENANTIOMER OF AN ALCOHOL REACTS FASTER IN THIS ACYLATION

被引：77

作者：

NAEMURA, K

FUKUDA, R

MURATA, M

KONISHI, M

HIROSE, K

TOBE, Y

机构：

[1] Department of Chemistry, Faculty of Engineering Science, Osaka University, Toyonaka, Osaka

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 09期

关键词：

D O I：

10.1016/0957-4166(95)00316-H

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Primary alcohols having a hydroxymethyl group at an S stereogemic center and secondary alcohols with an R configuration are preferentially acylated to give the corresponding acetates by lipase YS (from Pseudomonas fluorescens)-catalyzed acylation using isopropenyl acetate as the acylating agent in diisopropyl ether. On the basis of enantiomer selectivities observed, a predictive active site model for lipase YS is proposed for identifying which enantiomer of a primary or a secondary alcohol reacts faster in this acylation.

引用

页码：2385 / 2394

页数：10

共 46 条

[1] ENZYMATIC ESTER HYDROLYSIS AND SYNTHESIS - 2 APPROACHES TO CYCLOALKANE DERIVATIVES OF HIGH ENANTIOMERIC PURITY [J].