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

Authors
EICHHORN E RODUIT JP SHAW N HEINZMANN K KIENER A
Citation
E. Eichhorn et al., 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, Tetrahedron : asymmetry, 8(15), 1997, pp. 2533-2536
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
15
Year of publication
1997
Pages
2533 - 2536
Database
ISI
SICI code
0957-4166(1997)8:15<2533:PO(A(>2.0.ZU;2-8
Abstract
Whole bacterial cells containing stereospecific amidases were used for the kinetic resolution of racemic piperazine-2-carboxamide and piperi dine-2-carboxamide to (S)- and (R)-piperazine-2-carboxylic acid, and ( S)-piperidine-2-carboxylic acid, respectively. (S)-Piperazinecarboxyli c acid dihydrochloride produced with the biocatalysts Klebsiella terri gena DSM 9174 had an ee value of 99.4% (41% yield), and the ee value o f (R)-piperazinecarboxylic acid dihydrochloride obtained with Burkhold eria 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.