Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit

Org Lett. 2017 May 19;19(10):2514-2517. doi: 10.1021/acs.orglett.7b00747. Epub 2017 May 9.

Abstract

The synthesis of the Staphylococcus aureus strain M capsular polysaccharide repeating unit is reported. A postglycosylation oxidation strategy was utilized for the construction of the α-galactosaminuronic acid linkages, relying on a stereoselective 2-azido-4,6-O-di-tert-butylsilylidene galactopyranoside donor, for which the selectivity was assessed by model glycosylations. The α-fucosamine linkage was installed stereoselectively, using a reactive 2-azidofucosyl donor. An unexpected glycosidic bond cleavage during the TEMPO/PhI(OAc)2-mediated oxidation of a disaccharide intermediate was circumvented by a TEMPO/PhI(OAc)2-Pinnick oxidation protocol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycosylation
  • Molecular Structure
  • Oxidation-Reduction
  • Polysaccharides, Bacterial
  • Staphylococcus aureus*

Substances

  • Polysaccharides, Bacterial