NMR analyses of complex d-glucose anomerization.

Food Chem

Berlin Institute of Technology, Department of Food Chemistry and Food Analysis, Gustav-Meyer-Allee 25, TIB 4/3-1, D-13355 Berlin, Germany. Electronic address:

Published: November 2018

Analyzing the H 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 H 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 α-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.

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http://dx.doi.org/10.1016/j.foodchem.2018.05.100DOI Listing

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