'Gelozymes' in organic synthesis. Part 2: Candida rugosa lipase mediated synthesis of enantiomerically pure (S)-cyano(3-phenoxyphenyl)methyl butyrate

Citation
Nw. Fadnavis et al., 'Gelozymes' in organic synthesis. Part 2: Candida rugosa lipase mediated synthesis of enantiomerically pure (S)-cyano(3-phenoxyphenyl)methyl butyrate, TETRAHEDR-A, 12(12), 2001, pp. 1695-1699
Citations number
21
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
0957-4166 → ACNP
Volume
12
Issue
12
Year of publication
2001
Pages
1695 - 1699
Database
ISI
SICI code
0957-4166(20010716)12:12<1695:'IOSP2>2.0.ZU;2-F
Abstract
Significant changes in enantioselectivity (E) have been observed when the b utanoate ester of ()-1-hydroxy-1-(3-phenoxyphenyl)acetonitrile was subjecte d to hydrolysis in acetate buffer (pH 4.5 E=6.4) and alcoholysis with 1-but anol in hexane catalysed by Candida rugosa lipase (E=45). Enantiomerically pure (S)-butanoate ester so obtained (e.e. 98.4%) was converted to the corr esponding (S)-cyanohydrin using Pseudomonas cepacia (Amano Ps) gelozyme. Th is strategy overcomes the problem of separation of the unwanted (R)-ester f rom the (S)-cyanohydrin. (C) 2001 Elsevier Science Ltd. All rights reserved .