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

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.