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

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 dihydroch...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 8; no. 15; pp. 2533 - 2536
Main Authors Eichhorn, Eric, Roduit, Jean-Paul, Shaw, Nicholas, Heinzmann, Klaus, Kiener, Andreas
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.08.1997
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
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Summary: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)-piperazine-2-carboxylic acid with an ee value of 97.3% (20% yield) was isolated. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(97)00256-5