The effect of penultimate N-acetylgalactosamine 4-sulfate on chondroitin chain elongation

Carbohydr Res. 1986 Aug 15:151:207-12. doi: 10.1016/s0008-6215(00)90341-0.

Abstract

Previous work has shown that odd-numbered oligosaccharides containing nonreducing terminal, non-sulfated N-acetylgalactosamine (GalNAc) or 6-sulfated GalNAc are excellent acceptors for enzymic addition of glucuronic acid (GlcA). However, the presence of a 4-sulfated GalNAc group blocks further addition. We have now used even-numbered oligosaccharides (a mixture of 4-sulfated, 6-sulfated, and non-sulfated) as acceptors of [3H]GalNAc to investigate the effect of sulfate residues on the GalNAc in the penultimate position. 3H-Labeled oligosaccharides were partially degraded with chondroitin AC lyase. The labeled trisaccharides, consisting of the added [3H]GalNAc and the nonreducing terminal disaccharides of the oligosaccharide acceptors, were then characterized. Both non-sulfated and mono-sulfated 3H-trisaccharides were observed. However, the 3H-trisaccharides were shown by chromatography with prepared standards to be non-sulfated or to be sulfated only at the 6-position. Thus the oligosaccharides containing a 4-sulfated, penultimate GalNAc at the nonreducing end did not serve as acceptors for [3H]GalNAc. Microsomes from mastocytoma cells, which make only chondroitin 4-sulfate, exhibited the same substrate specificity for exogenous oligosaccharide acceptors as did microsomes from chick cartilage which makes chondroitin 6-sulfate.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acetylgalactosamine / analogs & derivatives*
  • Acetylgalactosamine / pharmacology
  • Animals
  • Chick Embryo
  • Chondroitin / analogs & derivatives*
  • Chondroitin Sulfates / biosynthesis*
  • Galactosamine / analogs & derivatives*
  • Growth Plate / metabolism
  • Mast-Cell Sarcoma / metabolism
  • Microsomes / metabolism*
  • Oligosaccharides / isolation & purification
  • Tritium
  • Uridine Diphosphate N-Acetylgalactosamine / metabolism*
  • Uridine Diphosphate Sugars / metabolism*

Substances

  • Oligosaccharides
  • Uridine Diphosphate Sugars
  • Tritium
  • N-acetylgalactosamine 4-sulfate
  • Uridine Diphosphate N-Acetylgalactosamine
  • Galactosamine
  • Chondroitin
  • Chondroitin Sulfates
  • Acetylgalactosamine