Synthesis of alpha-C(1 -> 3)-mannopyranoside of N-acetylgalactosamine, a new beta-galactosidase inhibitor.

Authors
Pasquarello, C Demange, R Vogel, P
Citation
C. Pasquarello et al., Synthesis of alpha-C(1 -> 3)-mannopyranoside of N-acetylgalactosamine, a new beta-galactosidase inhibitor., BIOORG MED, 9(5), 1999, pp. 793-796
Citations number
47
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
9
Issue
5
Year of publication
1999
Pages
793 - 796
Database
ISI
SICI code
0960-894X(19990308)9:5<793:SOA-3O>2.0.ZU;2-H
Abstract
Radical C-glycosidation of a 3-methylidene-7-oxabicyclo[2.2.1]heptan-2-one derivative with acetobromomannose gave a alpha-C-mannopyranoside that was c onverted into alpha-D-ManpCH(2)(1-->3)-D-GalNAc, a C-disaccharide that inhi bits beta-galactosidase from jack bean with IC50 = 9.4 mu M and K-i = 7.5 m u M (mixed mode of inhibition). (C) 1999 Elsevier Science Ltd. All rights r eserved.