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Org Biomol Chem. 2012 Nov 14;10(42):8524-32. doi: 10.1039/c2ob26131f. Epub 2012 Sep 26.

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

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Laboratoire des Glucides, FRE CNRS 3517, Institut de Chimie de Picardie, Université de Picardie Jules Verne, 33 rue Saint Leu, 80039 Amiens Cedex, France.


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.

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