A novel sulfated structure in the carbohydrate-protein linkage region isolated from porcine intestinal heparin

J Biol Chem. 1992 Jan 25;267(3):1528-33.

Abstract

A preparation of porcine stage 14 intestinal heparin, which contains Ser as a predominant amino acid, was used for isolation of the carbohydrate-protein linkage region of heparin. Two glycoserines were isolated in a molar ratio of 96:4 after an exhaustive digestion with a mixture of bacterial heparinase and heparitinases. Their structures were determined by composition analysis, heparitinase digestion, co-chromatography with an authentic glycoserine on high performance liquid chromatography, and by 500-MHz one- and two-dimensional 1H NMR spectroscopy. The structure of the major one is delta GlcA beta 1-3Gal beta 1-3Gal beta 1-4Xyl beta 1-O-Ser and that of the minor is delta GlcA beta 1-4GlcNAc(6-O-sulfate) alpha 1-4GlcA beta 1-3Gal beta 1-3Gal beta 1-4Xyl beta 1-O-Ser. The novel 6-O-sulfated GlcNAc residue was demonstrated to occur in the vicinity of the carbohydrate-protein linkage region. The Gal residues were nonsulfated, in contrast to the sulfated Gal structures recently discovered in the carbohydrate-protein linkage region of chondroitin sulfate proteoglycans. The structural features are discussed in relation to biosynthetic mechanisms of the heparin glycosaminoglycans.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Chromatography, High Pressure Liquid
  • Heparin / chemistry*
  • Heparin / isolation & purification
  • Heparin Lyase
  • Heparitin Sulfate / chemistry*
  • Heparitin Sulfate / isolation & purification
  • Intestines / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Oligosaccharides / chemistry
  • Oligosaccharides / isolation & purification
  • Polysaccharide-Lyases
  • Serine / analysis
  • Swine

Substances

  • Oligosaccharides
  • Serine
  • Heparin
  • Heparitin Sulfate
  • Polysaccharide-Lyases
  • Heparin Lyase
  • heparitinsulfate lyase