Microbial hydrolysis of glutaronitrile derivatives with Brevibacterium sp. R 312.
The enantiomerically pure (S)-cyano acids 3 and 4 can be obtained by biotransformation with Brevibacterium sp. R 312 of the corresponding prochiral dinitriles 5 and 6, respectively. The hydrolysis is probably a two step process involving a nitrile hydratase and an amidase. In connection with these investigations a facile method for the synthesis of racemic 4-cyano-3-hydroxybutanoic acid derivatives was developed.
Kerridge
A
A
Department of Biological Sciences, University of Exeter, Devon, U.K.
Parratt
J S
JS
Roberts
S M
SM
Theil
F
F
Turner
N J
NJ
Willetts
A J
AJ
D000581:Amidohydrolases / Q000378:metabolism; D001555:Benzene Derivatives; D001711:Biotransformation; D001951:Brevibacterium / Q000254:growth & development / Q000378:metabolism*; D002087:Butyrates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D006836:Hydro-Lyases / Q000378:metabolism; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
C091063:3-benzyloxy-4-cyanobutanoic acid; D001555:Benzene Derivatives; D002087:Butyrates; D009570:Nitriles; C091062:3-benzoyloxy-4-cyanobutanoic acid; D000581:Amidohydrolases; D006836:Hydro-Lyases; C048831:nitrile hydratase