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

Org Lett. 2015 Feb 20;17(4):928-31. doi: 10.1021/acs.orglett.5b00031. Epub 2015 Feb 6.

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Glycosylation
  • Molecular Structure
  • Polysaccharides, Bacterial / chemical synthesis*
  • Polysaccharides, Bacterial / chemistry
  • Polysaccharides, Bacterial / immunology
  • Staphylococcus aureus / chemistry*
  • Trisaccharides / chemical synthesis*
  • Trisaccharides / chemistry
  • Trisaccharides / immunology

Substances

  • Polysaccharides, Bacterial
  • Trisaccharides