Crystal structure of methyl 3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (methyl beta-D-laminarabioside) monohydrate

Carbohydr Res. 1992 Dec 31:237:33-43. doi: 10.1016/s0008-6215(92)84231-g.

Abstract

Crystals of methyl 3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (methyl beta-D-laminarabioside) belong to the orthorhombic system, space group P2(1)2(1)2, with a = 14.548(2), b = 24.252(7), c = 4.938(1) A, and Z = 4. The crystal structure was solved by the direct method and refined by the full-matrix least-squares procedure to an R-value of 0.062 for 1099 observed reflections in the X-ray data. The molecular structure is similar to that of beta-D-laminarabiose. The torsional angles around the glycosidic bonds are influenced by both the existence of an intramolecular hydrogen bond at O-4'... O-5 and the exo-anomeric effect. In the nonreducing residue, the exocyclic O-5-C-5-C-6-O-6 and C-4-C-5-C-6-O-6 torsional angles are (+)gauche and trans, respectively, whereas the corresponding torsional angles in the reducing residue are (-)gauche and (+)gauche. One water molecule cocrystallizes with each disaccharide, and the crystal structure is stabilized mainly by intra- and inter-molecular hydrogen bonds involving water molecules.

MeSH terms

  • Carbohydrate Conformation*
  • Carbohydrate Sequence
  • Disaccharides / chemistry*
  • Glucans / chemistry
  • Glucosides / chemistry*
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Sequence Data
  • Polysaccharides, Bacterial / chemistry
  • Water / chemistry
  • X-Ray Diffraction
  • beta-Glucans*

Substances

  • Disaccharides
  • Glucans
  • Glucosides
  • Polysaccharides, Bacterial
  • beta-Glucans
  • Water
  • laminaribiose
  • methyl laminarabioside
  • curdlan