Synthesis of five nona-β-(1→6)-d-glucosamines with various patterns of N-acetylation corresponding to the fragments of exopolysaccharide of Staphylococcus aureus

Carbohydr Res. 2011 May 15;346(7):905-13. doi: 10.1016/j.carres.2011.02.018. Epub 2011 Feb 23.

Abstract

A series of five 3-acetamidopropyl β-glycosides of nona-β-(1→6)-glucosamines containing two N-acetylglucosamine residues separated by a different number of glucosamine units with free amino groups have been synthesized using a convergent blockwise approach. Oxazoline glycosylation was used to introduce N-acetylglucosamine residues. These nonasaccharides are structurally related to the poly-N-acetylglucosamine (PNAG) extracellular polysaccharide of Staphylococcus aureus and can be used as models for biochemical and immunological studies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylglucosamine / analogs & derivatives*
  • Acetylglucosamine / chemistry
  • Carbohydrate Sequence
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligosaccharides / chemical synthesis*
  • Staphylococcus aureus / chemistry
  • beta-Glucans / chemical synthesis*

Substances

  • Oligosaccharides
  • beta-Glucans
  • poly-N-acetyl-1-6-glucosamine
  • Acetylglucosamine