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N-acetylhexosaminidase inhibitory properties of C-1 homologated GlcNAc- and GalNAc-thiazolines

TitleN-acetylhexosaminidase inhibitory properties of C-1 homologated GlcNAc- and GalNAc-thiazolines
Publication TypeJournal Article
Year of Publication2008
AuthorsAmorelli, B, Yang, C, Rempel, B, Withers, SG, Knapp, S
JournalBIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume18
Pagination2944-2947
Date PublishedMAY 1
ISSN0960-894X
Abstract

Several C-1 homologated GlcNAc-and GalNAc-thiazolines, as well as a related GalNAc-thiazole, have been prepared. The compounds are analogues of GlcNAc-thiazoline, a potent transition-state-mimicking inhibitor of retaining beta-N-acetylglycosaminidases. Kinetic evaluation of these fused pyranose-heterocycles against the bacterial N-acetylhexosaminidase SpHex suggests active site steric restrictions around the substrate anomeric carbon. (C) 2008 Elsevier Ltd. All rights reserved.

DOI10.1016/j.bmcl.2008.03.067