Shigella flexneri are Gram-negative enterobacteria responsible for bacillary dysentery. As an alternative to Shigella detoxified lipolysaccharide-protein conjugate vaccines under development, we have investigated synthetic oligosaccharide-based conjugates. We identified the synthetic pentadecasaccharide [AB(E)CD]3 as a promising functional mimic of S. flexneri 2a (SF2a) O-antigen, and a conjugate thereof as the first synthetic oligosaccharide-based vaccine candidate against SF2a infection. The non stoechiometric O-acetylation of SF2a O-antigen at OH-6D and OH-3A was disclosed recently.                    2)-a-L-Rhap-(1?2)-a-L-Rhap-(1?3)-[a-D-Glcp-(1?4)]-a-L-Rhap-(1?3)-�-D-GlcNAcp-(1?                                                     Basic repeating unit of SF2a O-antigen: AB(E)CDThis communication reports on our present understanding of the influence of O-acetylation on O-antigen:antibody recognition. First, we will expose the convergent synthesis of three [AB(E)CD]2 decasaccharides, mono- and/or di-O-acetylated at hydroxyls 3A and 6D, and emphasize on the crucial set of protecting groups involved. Next, we will discuss the binding of the synthetic decasaccharides, O-acetylated or not, to five protective monoclonal IgG antibodies.

Synthetic and immunochemical investigations on
a set of Shigella flexneri 2a O-acetylated decasaccharides

241st National Meeting (2011)

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Synthetic and immunochemical investigations on a set of Shigella flexneri 2a O-acetylated decasaccharides