N-Linked carba-disaccharides as potential inhibitors of glucosidases I and II

Abstract

An N-linked pseudodisaccharide 2 containing an inositol moiety in place of a glycopyranosyl residue has been synthesised to mimic the disaccharide unit, 3-O-(α-D-glucopyranosyl)-D-glucopyranose, cleaved by glucosidase II during glycoprotein processing. Its inhibitory action towards yeast α-glucosidase was inferior to that of 1-deoxynojirmycin, a known inhibitor of glucosidase II. An attempt to prepare the analogous 2-N-linked compound 1 as an inhibitor of glucosidase I led to the novel N-phenyl derivative 11 of 2-amino-2-deoxy-D-glucopyranose.