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Issue 42, 2012
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Synthesis and immunochemical evaluation of a non-methylated disaccharide analogue of the anthrax tetrasaccharide

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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.

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

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Supplementary files

Article information


Submitted
13 Jun 2012
Accepted
24 Aug 2012
First published
28 Aug 2012

Org. Biomol. Chem., 2012,10, 8524-8532
Article type
Paper

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

O. Milhomme, S. M. Köhler, D. Ropartz, D. Lesur, S. Pilard, F. Djedaïni-Pilard, W. Beyer and C. Grandjean, Org. Biomol. Chem., 2012, 10, 8524
DOI: 10.1039/C2OB26131F

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