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Synthesis of Staphylococcus aureus Type 5 trisaccharide repeating unit: solving the problem of lactamization.


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 ?-fucosylation and ?-mannosylation are addressed through the careful choice of protecting groups. Lactamization of a ?-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.

SUBMITTER: Gagarinov IA 

PROVIDER: S-EPMC4507426 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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Synthesis of Staphylococcus aureus Type 5 trisaccharide repeating unit: solving the problem of lactamization.

Gagarinov Ivan A IA   Fang Tao T   Liu Lin L   Srivastava Apoorva D AD   Boons Geert-Jan GJ  

Organic letters 20150206 4


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 tran  ...[more]

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