Study of the attachment of Na+ on glucose and on some of its methylated derivatives

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Abstract
The mechanism of attachment of Na+ on glucose, methyl-α-D-glucose, methyl-β-D-glucose, 3-O-methylglucose, tetra-O-methylglucose, and also on galactose and methyl-β-D-galactose, was studied. For this we measured the ion yields for the complex [sugar–Na+] formed by ionisation by matrix-assisted laser desorption/ionisation (MALDI) and ionspray. These data were compared with the relative volatilities and hydrophobicities of the sugars, measured by evaporative light scattering and reversed-phase liquid chromatography, respectively. Some formation enthalpies for the complexes [sugar–Na+], starting from the sugar and the cation, were obtained by ab initio calculations. No simple correlations could be observed between the ion yields and the parameters studied, so that the cationisation mechanism of the sugars remains unclear. Copyright © 2002 John Wiley & Sons, Ltd.