Conformation of the pentasaccharide corresponding to the binding site of heparin for antithrombin III

Carbohydr Res. 1990 Jan 15;195(2):169-85. doi: 10.1016/0008-6215(90)84165-q.

Abstract

The conformation in solution of the pentasaccharide methyl glycoside (As-G-A*-Is-AM; 1), which represents the binding site of heparin for Antithrombin III, has been investigated using molecular mechanics and 1H-n.m.r. spectroscopy. The pentasaccharide has a rather rigid (As-G-A*) and a more flexible (Is-AM) region. A simplified model of 1, comprising two conformations, corresponding to the 1C4 and the 2S0 forms of the iduronate residue, and modified at the G-A* glycosidic linkage with respect to the energy minimum, reproduces most of the observed 3J values and n.O.e. enhancements. The possible role in the binding to Antithrombin III of a low-energy conformer, not observed in solution, is discussed.

MeSH terms

  • Antithrombin III*
  • Binding Sites
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Disaccharides
  • Glucosamine
  • Heparin*
  • Iduronic Acid
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Models, Molecular
  • Molecular Sequence Data
  • Oligosaccharides
  • Thermodynamics

Substances

  • Disaccharides
  • Oligosaccharides
  • Iduronic Acid
  • Antithrombin III
  • Heparin
  • Glucosamine