Synthesis and immunochemical evaluation of a non-methylated disaccharide analogue of the anthrax tetrasaccharide?

Organic & Biomolecular Chemistry Pub Date: 2012-08-28 DOI: 10.1039/C2OB26131F

Abstract

Anthrax tetrasaccharide is an oligosaccharide expressed at the outermost surface of the Bacillus anthracis spores, featuring three rhamnoses and a rare sugar called anthrose. This motif has now been identified as a plausible component of future human vaccines against anthrax. We report herein the synthesis of a 2-O-demethylated-β-D-anthropyranosyl-(1→3)-α-L-rhamnopyranose disaccharide analogue of this tetrasaccharide from a cyclic sulfate intermediate. This disaccharide conjugated to BSA induces an anti-native tetrasaccharide IgG antibody response when administered in BALB/c mice. Moreover, induced sera bound to native B. anthracis endospores. These results suggest that the disaccharide analogue, easily amenable for a synthetic scale-up, could be used in a glycoconjugate antigen formulation.

Graphical abstract: Synthesis and immunochemical evaluation of a non-methylated disaccharide analogue of the anthrax tetrasaccharide
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