CHEMOENZYMATIC SYNTHESIS OF PROTECTED CYANO DERIVATIVES OF GLUTAMATE

Authors
DUGAVE C CLUZEAU J MENEZ A GAUDRY M MARQUET A
Citation
C. Dugave et al., CHEMOENZYMATIC SYNTHESIS OF PROTECTED CYANO DERIVATIVES OF GLUTAMATE, Tetrahedron letters, 39(32), 1998, pp. 5775-5778
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
32
Year of publication
1998
Pages
5775 - 5778
Database
ISI
SICI code
0040-4039(1998)39:32<5775:CSOPCD>2.0.ZU;2-H
Abstract
(2S,4RS)-Boc-4-cyanoglutamate gamma-methyl ester (ee = 95%) and (2S)-B oc-2-amino-4-bis(cyano)butyrate (ee = 96%) were synthesised in respect ively 43% and 40% overall yields by addition of sodium malonate deriva tives onto Boc-dehydroalanine methyl ester followed by regio- and ster eoselective hydrolysis of alpha-methyl ester by alpha-chymotrypsin. Th ese regio-and stereoselectivities were strongly dependent on the natur e of the gamma-substituents. (C) 1998 Elsevier Science Ltd. All rights reserved.