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© Research
Publication : Chemistry, an Asian journal

Efficient iterative synthesis of O-acetylated tri- to pentadecasaccharides related to the lipopolysaccharide of Shigella flexneri type 3a via di- and trisaccharide glycosyl donors

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Chemistry, an Asian journal - 01 Jul 2016

Hu Z, Bongat A, Mulard LA

Link to Pubmed [PMID] – 27385615

Chem Asian J 2016 Jul;

Protection against bacterial infections, including shigellosis, can be achieved by antibodies against the bacterial surface polysaccharide. In line with our efforts to develop vaccine candidates for shigellosis, we report the synthesis of penta-, deca-, and pentadecasaccharides as well as of tri-, octa-, and tridecasaccharides, as endchain and intrachain fragments, respectively, of the surface polysaccharide of Shigella flexneri 3a, a prevalent serotype. The syntheses rely on the efficiency of the trichloroacetimidate glycosylation chemistry, whereby iteration with di- and trisaccharide building blocks provided fragments made of up to three mono-O-acetylated polysaccharide repeating units. Pd(OH)2-mediated hydrogenation/hydrogenolysis enabled the concomitant removal or conversion of up to 31 protecting groups of four different origins to provide the targets as propyl glycosides. Oligosaccharides comprising the octasaccharide segment display high conformational similarities in solution.

https://www.ncbi.nlm.nih.gov/pubmed/27385615