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Synthesis 2018; 50(21): 4270-4282
DOI: 10.1055/s-0037-1609719
DOI: 10.1055/s-0037-1609719
paper
Zwitterionic Polysaccharides of Shigella sonnei: Synthetic Study toward a Ready-for-Oligomerization Building Block Made of Two Rare Amino Sugars
This work has received funding from the Institut Pasteur, the MENESR, France (ENS Cachan, PhD fellowship to H. P.) and the European Commission Seventh Framework Program (FP7/2007–2013) under Grant agreement No. 261472-STOPENTERICS, which included a fellowship to J.P.
Weitere Informationen
Publikationsverlauf
Received: 22. Februar 2018
Accepted after revision: 09. April 2018
Publikationsdatum:
05. Oktober 2018 (online)
Published as part of the Special Section on the 26th French–Japanese Symposium on Medicinal and Fine Chemistry.
Abstract
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609719.
- Supporting Information
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