Oligosaccharides related to xyloglucan: synthesis and X-ray crystal structure of methyl 2-0-(alpha-L-fucopyranosyl)-beta-D-galactopyranoside

Carbohydr Res. 1996 May 14:285:1-15. doi: 10.1016/s0008-6215(96)90160-3.

Abstract

The disaccharides methyl 2-O-(alpha-L-fucopyranosyl)-beta-D-galactopyranoside and methyl 2-O-(alpha-L-fucopyranosyl)-alpha-D-galactopyranoside have been synthesised using the assisted halide reaction of tri-O-benzyl-alpha-L-fucopyranosyl bromide with methyl 3,4,6-tri-O-benzyl-beta-D-galactopyranoside and methyl 3,4,6-tri-O-benzyl-alpha-D-galactopyranoside to construct the interresidue glycosidic linkages. A crystal structure of methyl 2-O-(alpha-L-fucopyranosyl)-beta-D-galactopyranoside was determined using Mo-K alpha X-ray data at 183 K. The space group is P1 (No. 1) with the unit cell containing two molecules of the disaccharide with unique conformations and a water molecule. The structure was refined to R = 0.0566 for 2969 reflections. The L-fucopyranosyl and D-galactopyranosyl residues have the nominal 1C4 and 4C1 conformations, respectively. The interresidue torsion angles are comparable with those generated in a recent molecular modelling study.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Crystallography, X-Ray
  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry*
  • Glucans*
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Molecular Sequence Data
  • Molecular Structure
  • Polysaccharides / chemistry*
  • Xylans*

Substances

  • Disaccharides
  • Glucans
  • Polysaccharides
  • Xylans
  • methyl 2-O-fucopyranosyl-galactopyranoside
  • xyloglucan