Zwitterionic Polysaccharides of Shigella sonnei: Synthetic Study toward a Ready-for-Oligomerization Building Block Made of Two Rare Amino Sugars

Published on Oct 18, 2018in Synthesis2.908
· DOI :10.1055/S-0037-1609719
Hélène B. Pfister4
Estimated H-index: 4
(Paris V: Paris Descartes University),
Julie Paoletti3
Estimated H-index: 3
(Pasteur Institute)
+ 2 AuthorsLaurence A. Mulard26
Estimated H-index: 26
(Pasteur Institute)
Shigellosis is an endemic diarrheal disease caused by Gram negative bacteria named Shigella. The most exposed polysaccharides of Shigella sonnei display a zwitterionic disaccharide repeating unit (AB) made of two rare amino sugars: [4)-α- l -AltpNAcA-(1→3)-β- d -FucpNAc4N-(1→]. An original synthesis of a ready-for-oligomerization AB disaccharide is reported. The targeted orthogonally protected disaccharide was synthesized from l -glucose and tetra-O-acetyl-β- d -glucosamine. The challenging introduction of the 4B-azido group masking the amino moiety of the AAT residue was performed at the disaccharide stage by a two-step procedure (triflation followed by nucleo­philic displacement with NaN3). A post-glycosylation oxidation strategy was employed to access the altruronate moiety.
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