Comparative 1H NMR study of hydroxy protons in galabioside and its S-linked 4-thiodisaccharide analogue in aqueous solution.
The NMR data obtained from hydroxy protons have been used to investigate the presence and absence of intramolecular hydrogen bonding in aqueous solutions of 2-(trimethylsilyl)ethyl galabioside (alpha-D-Galp-(1-->4)-beta-D-Galp-O(CH2)2SiMe3) and the S-linked 4-thiodisaccharide analogue. The data show that there is a weak hydrogen bond interaction between O-6H and O-2'H in galabioside, but not in the thio-analogue. The results are in good agreement with those reported for the substances in a Me2SO-d6 solution. It is also shown that the existence of a hydrogen bond can be quite easily monitored by comparing the NMR data of the hydroxy protons.
Sandström
C
C
Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala, Sweden.
Magnusson
G
G
Nilsson
U
U
Kenne
L
L
D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013865:Thioglycosides / Q000737:chemistry*
D004187:Disaccharides; D013865:Thioglycosides; C032103:4-O-alpha-D-galactopyranosyl-D-galactose