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American Chemical Society, Organic Letters, 4(17), p. 928-931, 2015

DOI: 10.1021/acs.orglett.5b00031

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Synthesis of Staphylococcus aureus Type 5 Trisaccharide Repeating Unit: Solving the Problem of Lactamization

Journal article published in 2015 by Ivan A. Gagarinov ORCID, Tao Fang, Lin Liu, Apoorva D. Srivastava, Geert-Jan Boons ORCID
This paper is available in a repository.
This paper is available in a repository.

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Abstract

The chemical synthesis of an orthogonally protected trisaccharide derived from the polysaccharide of Staphylococcus aureus Type 5, which is an attractive candidate for the development of immunotherapies, is described. The challenging α-fucosylation and β-mannosylation are addressed through the careful choice of protecting groups. Lactamization of a β-d-ManpNAcA moiety during deprotection was avoided by a late stage oxidation approach. Versatility of the trisaccharide was demonstrated by its transformation into a spacer-containing repeating unit suitable for immunological investigations.