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Royal Society of Chemistry, Organic and Biomolecular Chemistry, 42(10), p. 8524, 2012

DOI: 10.1039/c2ob26131f

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

This paper is available in a repository.
This paper is available in a repository.

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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.