The crystal and molecular structure of the trisaccharide erlose trihydrate

Carbohydr Res. 1994 Jan 3:251:203-12. doi: 10.1016/0008-6215(94)84286-8.

Abstract

Erlose [beta-D-fructofuranosyl O-alpha-D-glucopyranosyl-(1-->4)-D-glucopyranoside] trihydrate, C18H32 O16.3H2O, M(r) = 558.48, is orthorhombic, P2(1)2(1)2(1) with a = 31.164(7), b = 13.111(5), c = 11.636(5) A, and Z = 8. The structure was solved by direct methods, and refined to R = 0.035 for 3926 observed reflections. The unit cell contains two independent molecules having a similar conformation. The conformation of the alpha-(1-->2) glycosidic linkage is similar to that observed in erlose monohydrate, whereas the conformation of the alpha-(1-->4) glycosidic linkage differs significantly. The molecule has no intramolecular hydrogen-bonds except for the minor components of three-center bonds, but indirect intramolecular hydrogen-bonds through the water molecules are formed. The hydrogen-bond system in the crystal structure consists of infinite and finite chains crosslinked by water molecules.

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Cariostatic Agents / chemistry*
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Models, Chemical
  • Models, Molecular
  • Molecular Sequence Data
  • Sweetening Agents / chemistry*
  • Trisaccharides / chemistry*
  • Water / chemistry

Substances

  • Cariostatic Agents
  • Sweetening Agents
  • Trisaccharides
  • Water
  • glucosylsucrose