Artificial carbohydrate antigens: the synthesis of a tetrasaccharide hapten, a Shigella flexneri O-antigen repeating unit

Abstract

The 8-methoxycarbonyloctyl glycoside of the tetrasaccharide hapten, O-alpha-L-rhamnopyranosyl-(1 leads to 2)-O-alpha-L-rhamnopyranosyl-(1 leads to 3)-O-alpha-L-rhamnopyranosyl-(1 leads to 3)-2-acetamido-2-deoxy-beta-D-glucopyranoside and the trisaccharide glycoside 8-methoxycarbonyloctyl O-alpha-L-rhamnopyranosyl-(1 leads to 3)-O-alpha-L-rhamnopyranosyl-(1 leads to 3)-2-acetamido-2-deoxy-beta-D-glucopyranoside were synthesized by sequential Koenigs-Knorr reactions from monosaccharide units. The tetrasaccharide represents the complete skeletal repeating unit of Shigella flexneri serogroup Y lipopolysaccharide. Both oligosaccharide haptens are functionalized for covalent attachment to proteins, cell surfaces, and solid supports. 1H-N.m.r. evidence for the conformations of these oligosaccharides in solution is presented and shown to be consistent with predictions based on the exo-anomeric effect.