Preparation of (S)-piperazine-2-carboxylic acid, (R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic acid by kinetic resolution of the corresponding racemic carboxamides with stereoselective amidases in whole bacterial cells

被引：63

作者：

Eichhorn, E ^{[1
]}

Roduit, JP ^{[1
]}

Shaw, N ^{[1
]}

Heinzmann, K ^{[1
]}

Kiener, A ^{[1
]}

机构：

[1] LONZA AG,CH-3930 VISP,SWITZERLAND

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(97)00256-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Whole bacterial cells containing stereospecific amidases were used for the kinetic resolution of racemic piperazine-2-carboxamide and piperidine-2-carboxamide to (S)- and (R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic acid, respectively. (S)-Piperazinecarboxylic acid dihydrochloride produced with the biocatalysts Klebsiella terrigena DSM 9174 had an ee value of 99.4% (41% yield), and the ee value of (R)-piperazinecarboxylic acid dihydrochloride obtained with Burkholderia sp. DSM 9925 was 99.0% (22% yield). Using Pseudomonas fluorescens DSM 9924 (S)-piperidine-2-carboxylic acid with an ee value of 97.3% (20% yield) was isolated. (C) 1997 Elsevier Science Ltd.

引用

页码：2533 / 2536

页数：4

共 14 条

[1] SYNTHESIS AND NMDA ANTAGONISTIC PROPERTIES OF THE ENANTIOMERS OF 4-(3-PHOSPHONOPROPYL)PIPERAZINE-2-CARBOXYLIC ACID (CPP) AND OF THE UNSATURATED ANALOG (E)-4-(3-PHOSPHONOPROP-2-ENYL)PIPERAZINE-2-CARBOXYLIC ACID (CPP-ENE) [J].