5 years ago

Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit

Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit
J. Hessel M. van Dijk, Gijsbert A. van der Marel, Bas Hagen, Qingju Zhang, Jeroen D. C. Codée, Herman S. Overkleeft
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00747

DOI: 10.1021/acs.orglett.7b00747

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