Preparation of (R)- and (S)-4-chloro-3-acetoxybutyronitrile using microbial resolution

Citation
H. Idogaki et al., Preparation of (R)- and (S)-4-chloro-3-acetoxybutyronitrile using microbial resolution, TETRAHEDR-A, 12(3), 2001, pp. 369-373
Citations number
12
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
0957-4166 → ACNP
Volume
12
Issue
3
Year of publication
2001
Pages
369 - 373
Database
ISI
SICI code
0957-4166(20010305)12:3<369:PO(A(U>2.0.ZU;2-Q
Abstract
A new preparation of optically active 4-chloro-3-acetoxybutyronitrile (AcBN ) was developed using the resting cells of bacteria. The resolution was bas ed on enantioselective hydrolysis of the ester function of the substrate. ( R)-AcBN was prepared using Pseudomonas sp. DS-K-717, and the resulting (R)- AcBN was obtained with high enantiomeric excess of >98% with a yield of 36% during the microbial resolution step. (S)-AcBN was prepared in the same ma nner using the resting cells of Pseudomonas sp. DS-K-19 and showed a high e nantiomeric excess of >98%, with a yield of 32%. The enzyme activity was en hanced and induced by the addition of AcBN, particularly the (R)-ester hydr olysis, which was enhanced 20-fold. (C) 2001 Elsevier Science Ltd. All righ ts reserved.