A Conformational Study of Hydroxymethyl Groups in Carbohydrates Investigated by 1H NMR Spectroscopy
- 1 June 1994
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 13 (4) , 513-543
- https://doi.org/10.1080/07328309408011662
Abstract
It is generally acknowledged that information about carbohydrate conformation is important for the understanding of interaction between carbohydrates and other biomolecules, such as proteins.1–5 The major part of oligosaccharides involved in the interactions are made up of hexopyranoses, and the overall conformation can be described by the rotation of the glycosidic linkages and the bonds to the exocyclic groups,6,7 e.g., the hydroxymethyl groups and N-Acetyl groups. The conformation of the hydroxymethyl group is of interest for interactions involving the hydroxyl group at this position.2,8,9 Furthermor, the conformation of the C5-C6 linkage determines the overall shape of oligosaccharides with glycosidic linkages to 06.10–27 The conformational preferences of the hydroxymethyl group in mono and oligosaccharides have therefore been the subject of several investigations including both experimental and theoretical studies, as will be discussed in the following.Keywords
This publication has 115 references indexed in Scilit:
- Picosecond dynamics of simple monosaccharides as probed by NMR and molecular dynamics simulationsJournal of the American Chemical Society, 1993
- Critical evaluation of an empirically modified Karplus equationMagnetic Resonance in Chemistry, 1992
- Conformation of 1,2-dimethoxyethane in the gas phase: a rotational isomeric state simulation of NMR vicinal coupling constantsThe Journal of Physical Chemistry, 1992
- The solution conformation of sialyl-α(2→6)-lactose studied by modern NMR techniques and Monte Carlo simulationsJournal of Biomolecular NMR, 1992
- Chiral hydroxymethyl groups: 1H NMR assignments of the prochiral C‐5′ protons of ribonucleosidesMagnetic Resonance in Chemistry, 1988
- Empirical determination of the torsion angle dependence of the vicinal 13C‐H coupling constant in a 13CH3‐C(R1)OH‐C(R2)H‐*H fragment of model compoundsRecueil des Travaux Chimiques des Pays-Bas, 1978
- The Effects of Steric Compression on Chemical Shifts in Half-Cage and Related Molecules1,2Journal of the American Chemical Society, 1965
- Dependency of Vicinal Coupling Constants on the Configuration of Electrongegative SubstituentsJournal of the American Chemical Society, 1964
- Vicinal Proton Coupling in Nuclear Magnetic ResonanceJournal of the American Chemical Society, 1963
- Bond Energies and Polarities1Journal of the American Chemical Society, 1953