4-O-methyl-beta-L-idopyranosyluronic acid linked to xylan from kraft pulp: isolation procedure and characterisation by NMR spectroscopy

Carbohydr Res. 1996 Oct 23;293(1):1-13. doi: 10.1016/0008-6215(96)00170-x.

Abstract

The tetrasaccharide 2"-O-(4-O-methyl-beta-L-idopyranosyluronic acid)xylotriose was isolated from enzymatically hydrolysed, unbleached, birch kraft pulp by anion-exchange chromatography in two steps. The primary structure of the tetrasaccharide was determined by 1H and 13C NMR spectroscopy, using homonuclear and heteronuclear two-dimensional techniques. NOE data and 3JH,H coupling constants show that the 4-O-methyl-beta-L-idopyranosyluronic acid in the tetrasaccharide is predominantly in the 1C4 chair conformation. The pKa value (3.17) for 4-O-methyliduronic acid attached beta-(1-->2) to xylose was determined from the pH-dependent chemical shift of H-5. The amount of 4-O-methyliduronic acid (0.1-0.5 mol%) in surface xylan of unbleached birch and pine kraft pulps was determined by extensive xylanase treatment and further analysis by NMR spectroscopy and high-performance anion-exchange chromatography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Chromatography, High Pressure Liquid
  • Iduronic Acid / analogs & derivatives*
  • Iduronic Acid / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Molecular Structure
  • Monosaccharides / analysis
  • Oligosaccharides / chemistry*
  • Uronic Acids / chemistry*
  • Uronic Acids / isolation & purification*
  • Wood
  • Xylans / chemistry*

Substances

  • 4-O-methylidopyranosyluronic acid
  • Monosaccharides
  • Oligosaccharides
  • Uronic Acids
  • Xylans
  • Iduronic Acid