Structural studies on sulfated oligosaccharides derived from the carbohydrate-protein linkage region of chondroitin 6-sulfate proteoglycans of shark cartilage. I. Six compounds containing 0 or 1 sulfate and/or phosphate residues

J Biol Chem. 1992 Mar 25;267(9):6027-35.

Abstract

Shark cartilage proteoglycans bear predominantly chondroitin 6-sulfate. After exhaustive protease digestion, reductive beta-elimination, and subsequent chondroitinase ABC digestion, 13 hexasaccharide alditols, which are nonsulfated, sulfated, and/or phosphorylated, were obtained from the carbohydrate-protein linkage region. Six compounds, containing 0 or 1 sulfate and/or phosphate residue, represent approximately 40% of the isolated linkage hexasaccharide alditols. They were analyzed by chondroitinase ACII or alkaline phosphatase digestion in conjunction with high performance liquid chromatography, and by 500 MHz one- and two-dimensional 1H NMR spectroscopy. All six compounds have the conventional structure in common. Delta 4,5-GlcA beta 1-3GalNAc beta 1-4GlcA beta 1-3Gal beta 1-3Gal beta 1-4Xyl-ol One compound has no sulfate nor phosphate. Two of the monosulfated compounds have a O-sulfate on C-6 or on C-4 of the GalNAc residue. The third monosulfated compound has a novel O-sulfate on C-6 of the Gal residue attached to xylitol. The two phosphorylated compounds have O-phosphate on C-2 of Xyl-ol, and one of them has in addition sulfate on C-6 of GalNAc.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Cartilage / chemistry*
  • Chondroitin Sulfate Proteoglycans / chemistry*
  • Chondroitin Sulfate Proteoglycans / isolation & purification
  • Chromatography, Gel
  • Chromatography, High Pressure Liquid
  • Disaccharides / chemistry
  • Disaccharides / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Oligosaccharides / chemistry*
  • Oligosaccharides / isolation & purification
  • Peptidoglycan / chemistry*
  • Peptidoglycan / isolation & purification
  • Phosphates / analysis
  • Sharks
  • Sulfuric Acids / analysis

Substances

  • Chondroitin Sulfate Proteoglycans
  • Disaccharides
  • Oligosaccharides
  • Peptidoglycan
  • Phosphates
  • Sulfuric Acids