The nuclear Overhauser effect and structural factors determining the conformation of disaccharides

Conformational analysis of 1.2-, 1.3- and 1.4-linked disaccharides built up of aldohexapyranose residues was performed on the basis of interresidue nuclear Overhauser effects in 1H-NMR spectra and theoretical calculation using atom-atom potential functions. It was shown that the preferred conformation of the disaccharides is determined by the following factors: absolute configurations of monosaccharide residues, configuration and position of the glycosidic linkage, orientation of protons at the aglycon carbon atom involved in the glycosidic linkage and at the adjacent carbons atoms.