jo035125b_si_001.pdf (1.92 MB)
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 Unit1
journal contribution
posted on 2004-02-20, 00:00 authored by Frédéric Bélot, Karen Wright, Corina Costachel, Armelle Phalipon, Laurence A. MulardThe 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.