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Influence of glycosidic linkage on the solution conformational entropy of gluco- and mannobioses

Published

Author(s)

Andre M. Striegel, Mallory J. Morris

Abstract

Employing size-exclusion chromatography, an entropically-controlled separation technique, we have determined the solution conformational entropy (-delta S) of (1-2)-, (1-3)-, (1-4)-, and (1-6)-linked gluco- and mannobioses with an alpha anomeric configuration, at quasi- physiological conditions of solvent, temperature, and pH. The experiments allowed for comparison both among and between each series of disaccharides. Results included quantitative information on how the additional degrees of freedom of the (1-6) linkage influence -delta S, as well as on the influence on solution conformational entropy of a single axial hydroxyl (OH) group and of the relative positioning of the glycosidic linkage and the anomeric hydroxyl group. We also contrasted the alpha-(1-4)-linked gluco- and mannobioses to their counterparts with a beta anomeric configuration. Comparison between beta-(1-4)-linked glucobiose (cellobiose) and alpha-(1-4)-linked mannobiose showed that the restrictive effect on solution flexibility of the axial OH in the latter disaccharide is offset by the combined effect of hydroxyl group orientation and anomeric configuration on intramolecular hydrogen bonding.
Citation
Carbohydrate Research

Keywords

Solution conformational entropy, size-exclusion chromatography, glucobioses, mannobioses, glycosidic linkage, anomeric configuration

Citation

Striegel, A. and Morris, M. (2014), Influence of glycosidic linkage on the solution conformational entropy of gluco- and mannobioses, Carbohydrate Research, [online], https://doi.org/10.1016/j.carres.2014.06.022 (Accessed May 26, 2024)

Issues

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Created September 19, 2014, Updated January 27, 2020