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

作者：Laurence, Mulard; Hélène, Pfister; Julie, Paoletti; Ana, Poveda; Jesus, Jimenez-Barbero

来源：Synthesis (Germany), 2018, 50(21): 4270-4282.

DOI：10.1055/s-0037-1609719

<jats:p>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.</jats:p>

• 出版日期2018-11
• 单位常州工学院