Characterization of di- and monosulfated, unsaturated heparin disaccharides with terminal N-sulfated 1,6-anhydro-beta-D-glucosamine or N-sulfated 1,6-anhydro-beta-D-mannosamine residues

Carbohydr Res. 2007 May 7;342(6):835-42. doi: 10.1016/j.carres.2006.12.010. Epub 2006 Dec 21.

Abstract

Modified heparin disaccharides were obtained by the alkaline treatment of a solution containing the disulfated heparin disaccharide DeltaHexA-alpha-(1-->4)-D-GlcNSO(3),6SO(3). Their structures were characterized by one- and two-dimensional NMR spectroscopy: DeltaHexA-alpha-(1-->4)-1,6-anhydro-GlcNSO(3), DeltaHexA-alpha-(1-->4)-1,6-anhydro-ManNSO(3) and DeltaHexA-alpha-(1-->4)-ManNSO(3),6OSO(3). NMR spectroscopy, in combination with HPLC, provided the composition of the mixture. Characteristic NMR signals of the disaccharides were identified, even at low levels, in a high field of (1)H-(13)C correlation NMR spectra (HSQC) of a low molecular weight heparin (LMWH) obtained by beta-elimination (alkaline hydrolysis) of heparin benzyl ester, providing a more complete structural profile of this class of compounds.

MeSH terms

  • Carbohydrate Conformation
  • Chromatography, High Pressure Liquid
  • Disaccharides / chemistry*
  • Heparin / analogs & derivatives*
  • Heparin / chemistry
  • Heparin, Low-Molecular-Weight / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Oligosaccharides / chemistry*
  • Sulfates / chemistry*

Substances

  • Disaccharides
  • Heparin, Low-Molecular-Weight
  • Oligosaccharides
  • Sulfates
  • heparin disaccharide
  • Heparin