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 β-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.

Graphical abstractSeveral C-l homologated pyranose-fused thiazolines and a GalNAc-thiazole were evaluated as inhibitors of the bacterial N-acetylhexosaminidase SpHex; kinetic analysis suggests active site steric restrictions around the anomeric carbon.Figure optionsDownload full-size imageDownload as PowerPoint slide