Synthesis of the methyl glycoside of a branched octasaccharide fragment specific for the Shigella flexneri serotype 2a O-antigen

Frédéric Bélot (1) , Corina Costachel (1, 2) , Karen Wright (1) , Armelle Phalipon (2) , Laurence S Mulard (1)

1 Chimie Organique
2 Pathogénie Microbienne Moléculaire

An efficient synthesis of the methyl glycoside of a branched octasaccharide representative of Shigella flexneri serotype 2a O-specific polysaccharide is described. The synthesis is based on the use of the trichloroacetimidate methodology, and involves the condensation of a pentasaccharide acceptor and a trisaccharide donor as the key step. The target octasaccharide was synthesized efficiently according to a strategy based on the condensation of a pentasaccharide acceptor and a trisaccharide donor as the key step.

Mots clés: bacterial oligosaccharides; Shigella flexneri; chemical glycosylation

Domaines: Bactériologie

Frédéric Bélot, Corina Costachel, Karen Wright, Armelle Phalipon, Laurence S Mulard. Synthesis of the methyl glycoside of a branched octasaccharide fragment specific for the Shigella flexneri serotype 2a O-antigen. Tetrahedron Letters, 2002, 43 (46), pp.8215-8218. ⟨10.1016/S0040-4039(02)02055-5⟩. ⟨pasteur-02875035⟩