Transition-state model for subtilisin-catalyzed transesterifications of secondary alcohols

Authors
Ema, T Okada, R Fukumoto, M Jittani, M Ishida, M Furuie, K Yamaguchi, K Sakai, T Utaka, M
Citation
T. Ema et al., Transition-state model for subtilisin-catalyzed transesterifications of secondary alcohols, TETRAHEDR L, 40(23), 1999, pp. 4367-4370
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
23
Year of publication
1999
Pages
4367 - 4370
Database
ISI
SICI code
0040-4039(19990604)40:23<4367:TMFSTO>2.0.ZU;2-L
Abstract
In the subtilisin-catalyzed transesterifications of a variety of secondary alcohols, the (S)- enantiomers were acylated faster. Kinetic measurements i ndicated that the enantioselectivity originates from chiral discrimination in the transition state. A transition-state model capable of explaining the S-preference of subtilisin toward secondary alcohols has been proposed. (C ) 1999 Elsevier Science Ltd. All rights reserved.