NMR analyses of complex D-glucose anomerization

摘要

Analyzing the H-1 NMR spectrum of D-glucose, the resonance frequencies of the anomeric protons of five D-glucose anomers could be determined in dependence on temperature. Besides, the relative concentrations of all cyclic D-glucose anomers could be quantified. Based on that, thermodynamic parameters were calculated. In addition, ring opening rate constants of all cyclic D-glucose anomers were measured for the first time using 1H selective blind saturation transfer NMR spectroscopy. The results presented here give rise to the assumption that furanoid anomers highly influence the reactivity of total D-glucose. Finally, the complex anomeric equilibration curves for a freshly prepared solution of crystalline alpha-D-glucopyranose are presented. Based on that, it is hypothesized that the reactivity of a solution of a reducing sugar in general and D-glucose in particular depends on time until the thermodynamic equilibrium state is reached.