The synthesis and hydrolytic stability of 1-glucopyranosylimidazoles

Abstract

The synthesis of 1-α- and -β-D-glucopyranosylimidazoles via their tetra-acetates and their structural characterisation are described. The sugar–base linkage in these glycosylamines has been found to be extremely resistant to cleavage under a variety of hydrolytic conditions. The significance of this finding to the understanding of the mechanisms of nucleoside hydrolyses and of the role of histidine in glycosidase action is discussed.