The conformation of the monomethyl ethers of methyl beta-lactoside in D2O and Me2SO-d6 solutions

Carbohydr Res. 1993 Oct 4:248:15-36. doi: 10.1016/0008-6215(93)84113-k.

Abstract

The solution conformations of all the possible monomethyl ethers of methyl beta-lactoside have been analysed using molecular mechanics and dynamics calculations and nuclear magnetic resonance data (variable temperature and NOE experiments). The overall shape of all the compounds studied is fairly similar and may be described by conformers included in a low-energy region with phi = -100 +/- 40 degrees and psi = -135 +/- 35 degrees, which is ca. 5% of the total potential energy surface for the glycosidic linkages of the disaccharides.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Deuterium Oxide
  • Dimethyl Sulfoxide
  • Ethers
  • Magnetic Resonance Spectroscopy / methods
  • Methylglycosides / chemistry*
  • Models, Molecular
  • Molecular Sequence Data
  • Solutions
  • Structure-Activity Relationship

Substances

  • Ethers
  • Methylglycosides
  • Solutions
  • methyl lactoside
  • Deuterium Oxide
  • Dimethyl Sulfoxide