Synthesis and immunochemical evaluation of a non-methylated disaccharide analogue of the anthrax tetrasaccharide
2012
Milhomme, Ophélie | Köhler, Susanne | Ropartz, David | Lesur, David | Pilard, Serge | Pilard, Florence | Beyer, Wolfgang | Grandjean, Cyrille | Unité de recherche sur les Biopolymères, Interactions Assemblages (BIA) ; Institut National de la Recherche Agronomique (INRA) | Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A) ; Université de Picardie Jules Verne (UPJV)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS) | Plateforme Analytique - UPJV (PFA) ; Université de Picardie Jules Verne (UPJV) | Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST) ; Université de Nantes (UN) | Direction Generale de l'Armement; Deutsche Forschung Gesellschaft (DFG) [BE 2157/3-]
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Mostrar más [+] Menos [-]Inglés. 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-beta-D-anthropyranosyl-(1 -> 3)-alpha-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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