脂肪酶催化的未活化脂环稠合β-内酰胺在有机溶剂中的对映选择性开环反应。

Lipase-catalyzed enantioselective ring opening of unactivated alicyclic-fused beta-lactams in an organic solvent.

作者信息

Forró Eniko, Fülöp Ferenc

机构信息

Institute of Pharmaceutical Chemistry, University of Szeged, P.O. Box 121, H-6701 Szeged, Hungary.

出版信息

Org Lett. 2003 Apr 17;5(8):1209-12. doi: 10.1021/ol034096o.

DOI:10.1021/ol034096o

PMID:12688721

Abstract

[reaction: see text] A highly efficient and very simple method was developed for the synthesis of enantiopure beta-amino acids (e.g. cispentacin) and beta-lactams through the enzyme-catalyzed enantioselective ring opening of unactivated alicyclic beta-lactams in organic media. High enantioselectivity (E > 200) was observed when the Lipolase (lipase B from Candida antarctica)-catalyzed reactions were performed with H(2)O (1 equiv) in diisopropyl ether at 60 degrees C. The resolved products, obtained in good chemical yield (36-47%), could be easily separated.

摘要

[反应：见正文] 开发了一种高效且非常简单的方法，通过在有机介质中酶催化未活化的脂环族β-内酰胺的对映选择性开环来合成对映体纯的β-氨基酸（如西喷他辛）和β-内酰胺。当在60℃下于二异丙醚中用H₂O（1当量）进行脂肪酶（来自南极假丝酵母的脂肪酶B）催化的反应时，观察到高对映选择性（E＞200）。以良好的化学产率（36 - 47%）得到的拆分产物易于分离。