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

Article abstract of DOI:10.1016/S0957-4166(97)00256-5

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.