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A 1H-NMR and MD study of intramolecular hydrogen bonds in methyl beta-cellobioside
B R Leeflang1, J F Vliegenthart, L M Kroon-Batenburg
1Department of Bio-organic Chemistry, Bijvoet Center, Utrecht University, Netherlands.
Carbohydrate Research
|June 4, 1992
Abstract:
The existence of an HO-3...O-5' intramolecular hydrogen bond in methyl beta-cellobioside in solution in Me2SO-d6 and H2O-CD3OD (4:1 w/w) was studied by 500-MHz 1H-NMR spectroscopy and MD simulations. Temperature coefficients for the chemical shift of the hydroxyl resonances in these solvents were determined and the rates of proton exchange in the latter solvent were obtained from NOE data. With H2O-CD3OD as the solvent, the HO-3...O-5' hydrogen bond was insignificant, but its presence in Me2SO-d6 was confirmed.