OXYNITRILASE-CATALYZED TRANSFORMATION OF SUBSTITUTED ALDEHYDES - THE CASE OF (+ -)-2-PHENYLPROPIONALDEHYDE AND OF (+/-)-3-PHENYLBUTYRALDEHYDE/

Authors
DANIELI B BARRA C CARREA G RIVA S
Citation
B. Danieli et al., OXYNITRILASE-CATALYZED TRANSFORMATION OF SUBSTITUTED ALDEHYDES - THE CASE OF (+ -)-2-PHENYLPROPIONALDEHYDE AND OF (+/-)-3-PHENYLBUTYRALDEHYDE/, Tetrahedron : asymmetry, 7(6), 1996, pp. 1675-1682
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
6
Year of publication
1996
Pages
1675 - 1682
Database
ISI
SICI code
0957-4166(1996)7:6<1675:OTOSA->2.0.ZU;2-N
Abstract
The influence of a stereocenter already present in the molecule on the selectivity displayed by almond oxynitrilase has been addressed, cons idering the substituted aldehydes (+/-)-2-phenylpropionaldehyde 1 and (+/-)-3-phenylbutyraldehyde 2 as model substrates. Only when the stere ocenter was adjacent to the aldehyde group (as in 1) a strong influenc e on the selectivity of this enzyme was observed, resulting in the for mation of the four possible cyanohydrins although in different ratio. On the other hand, the cyanohydrins obtained from 2 had the expected 2 R configuration. Copyright (C) 1996 Elsevier Science Ltd