Methyl beta-D-galactopyranosyl-(1-->4)-beta-D-allopyranoside tetrahydrate

Acta Crystallogr C. 2010 Sep;66(Pt 9):o484-7. doi: 10.1107/S0108270110029471. Epub 2010 Aug 21.

Abstract

The title compound, C(13)H(24)O(11).4H(2)O, (I), crystallized from water, has an internal glycosidic linkage conformation having phi' (O5(Gal)-C1(Gal)-O1(Gal)-C4(All)) = -96.40 (12) degrees and psi' (C1(Gal)-O1(Gal)-C4(All)-C5(All)) = -160.93 (10) degrees , where ring-atom numbering conforms to the convention in which C1 denotes the anomeric C atom, C5 the ring atom bearing the exocyclic hydroxymethyl group, and C6 the exocyclic hydroxymethyl (CH(2)OH) C atom in the betaGalp and betaAllp residues. Internal linkage conformations in the crystal structures of the structurally related disaccharides methyl beta-lactoside [methyl beta-D-galactopyranosyl-(1-->4)-beta-D-glucopyranoside] methanol solvate [Stenutz, Shang & Serianni (1999). Acta Cryst. C55, 1719-1721], (II), and methyl beta-cellobioside [methyl beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranoside] methanol solvate [Ham & Williams (1970). Acta Cryst. B26, 1373-1383], (III), are characterized by phi' = -88.4 (2) degrees and psi' = -161.3 (2) degrees , and phi' = -91.1 degrees and psi' = -160.7 degrees , respectively. Inter-residue hydrogen bonding is observed between O3(Glc) and O5(Gal/Glc) in the crystal structures of (II) and (III), suggesting a role in determining their preferred linkage conformations. An analogous inter-residue hydrogen bond does not exist in (I) due to the axial orientation of O3(All), yet its internal linkage conformation is very similar to those of (II) and (III).

Publication types

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

MeSH terms

  • Crystallography, X-Ray
  • Hexoses / chemistry*
  • Hydrogen Bonding
  • Methylation
  • Models, Molecular
  • Molecular Conformation
  • Water / chemistry*

Substances

  • Hexoses
  • Water