Methyl 4-O-β-D-xylopyranosyl β-D-mannopyranoside, a core disaccharide of an antifreeze glycolipid

Acta Crystallogr C. 2013 Sep;69(Pt 9):1047-50. doi: 10.1107/S0108270113019021. Epub 2013 Aug 7.

Abstract

Methyl β-D-xylopyranosyl-(1→4)-β-D-mannopyranoside, C12H22O10, crystallized as colorless block-like needles from methanol-water solvent. Comparisons to the internal linkage conformations in the two crystallographic forms of the structurally related disaccharide methyl β-D-mannopyranosyl-(1→4)-β-D-xylopyranoside are discussed. Intramolecular inter-residue hydrogen bonding is observed between one mannopyranosyl hydroxy O atom and the ring O atom of the xylopyranosyl residue. Intermolecular hydrogen bonding yields a bilayered two-dimensional sheet of molecules that are located parallel to the bc plane.

Keywords: antifreeze glycolipid; crystal structure; disaccharides.

Publication types

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

MeSH terms

  • Antifreeze Proteins / chemistry*
  • Crystallography, X-Ray
  • Disaccharides / chemistry*
  • Water / chemistry
  • Xylose / analogs & derivatives*
  • Xylose / chemistry*

Substances

  • Antifreeze Proteins
  • Disaccharides
  • methyl 4-O-beta-D-mannopyranosyl beta-D-xylopyranoside
  • Water
  • Xylose