The structure of the glycopeptides from the fish pathogen Flavobacterium columnare

Carbohydr Res. 2003 Nov 14;338(23):2653-8. doi: 10.1016/j.carres.2003.08.012.

Abstract

Proteolytic digestion of the phenol-water extraction product of the fish pathogen Flavobacterium columnare afforded a mixture of glycopeptides in which the oligosaccharide moiety was an unusual hexasaccharide composed of 4-O-methyl-2-acetamido-2-deoxy-D-glucuronic acid (GlcNAcA), D-glucuronic acid (D-GlcA), 2,3-di-O-acetyl-D-xylose (D-Xyl), 2-O-methyl-D-glucuronic acid (D-GlcA), D-mannose (D-Man), and 2-O-methyl-L-rhamnose (L-Rha). By the application of high-resolution 1D and 2D NMR, mass spectrometry, and chemical analysis, the hexasaccharide structure was determined to be: [carbohydrate structure--see text] where all monosaccharides have the D-configuration except for 2-O-methyl-L-rhamnose; and were in the pyranose form. Only one carbohydrate structure was found. The peptide part was represented by tri- to hepta-peptides with a minimal common tripeptide fragment Asp-Ser-Ala, extended with Ala and Val.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbohydrate Sequence
  • Fishes / microbiology*
  • Flavobacterium / metabolism*
  • Glycopeptides / chemistry*
  • Glycoproteins / chemistry
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Sequence Data
  • Phenol / chemistry
  • Polysaccharides, Bacterial / chemistry
  • Water / chemistry

Substances

  • Glycopeptides
  • Glycoproteins
  • Polysaccharides, Bacterial
  • Water
  • Phenol