Synthesis of the Staphylococcus aureus Strain M Capsular Polysaccharide Repeating Unit

[Image: see text] 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-butylsilyli...

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Detalles Bibliográficos
Autores principales: Hagen, Bas, van Dijk, J. Hessel M., Zhang, Qingju, Overkleeft, Herman S., van der Marel, Gijsbert A., Codée, Jeroen D. C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5442609/
https://www.ncbi.nlm.nih.gov/pubmed/28485610
http://dx.doi.org/10.1021/acs.orglett.7b00747
Descripción
Sumario:[Image: see text] 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.

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