672907-39-0Relevant academic research and scientific papers
Synthesis of two linear PADRE conjugates bearing a deca- or pentadecasaccharide B epitope as potential synthetic vaccines against Shigella flexneri serotype 2a infection
Belot, Frederic,Guerreiro, Catherine,Baleux, Francoise,Mulard, Laurence A.
, p. 1625 - 1635 (2007/10/03)
The blockwise synthesis of the 2-aminoethyl glycosides of a deca- and a pentadecasaccharide made of two and three repeating units, respectively, of the Shigella flexneri serotype 2a specific polysaccharide is reported. The strategy relies on trifluoromethanesulfonic acid mediated glycosylation of a pentasaccharide building block acting as a glycosyl donor and a potential glycoside acceptor. Both targets were made available in amounts large enough for their subsequent conversion into glycoconjugates. Indeed, efficient elongation of the spacer through an acetylthioacetyl moiety and subsequent conjugation onto a Pan HLA DR-binding epitope (PADRE) T-cell-universal peptide resulted in two fully synthetic neoglycopeptides, which will be evaluated as potential vaccines against S. flexneri serotype 2a infections.
Blockwise Approach to Fragments of the O-Specific Polysaccharide of Shigella flexneri Serotype 2a: Convergent Synthesis of A Decasaccharide Representative of a Dimer of the Branched Repeating Unit
Belot, Frederic,Wright, Karen,Costachel, Corina,Phalipon, Armelle,Mulard, Laurence A.
, p. 1060 - 1074 (2007/10/03)
The D′A′B′(E′)C′DAB(E)C decasaccharide representative of a dimer of a frame-shifted pentasaccharide repeating unit of the O-specific polysaccharide of Shigella flexneri 2a was synthesized as its methyl glycoside by condensing a pentasaccharide donor (D′A′B′ (E′)C′) and a pentasaccharide acceptor (DAB(E)C-OMe). Several convergent routes to these two building blocks, involving either the AB linkage or the BC linkage as the disconnection site, were evaluated in comparison to the linear strategy. The latter was preferred. It is based on the use of the trichloroacetimidate chemistry. The target branched oligosaccharide was designed to probe the recognition at the molecular level of the natural polysaccharide by protective monoclonal antibodies.
