Variation in the hydrophilicity of hexapyranose sugars explains features of the anomeric effect

Abstract

For the complete family of aldopyranoses, the relative amounts of α and β anomers present in aqueous solution can be explained solely in terms of the relative hydrophilicities of the anomeric pairs. Hydrophilicity is defined here as the probability that a water ⋯ solute hydrogen bond will from, and a method for its calculation is described. The hydrophilicities of the sugars also correlate with a number of, previously uninterpretable, thermodynamic data which shows the structure-breaking effect of sugar solutions follows the order glucose > mannose > galactose.