Abstract
Although d-glucose is the most common sugar in nature, only a few NMR studies have focused on its minor furanose forms, and they have been limited to the anomeric position. Here, complete 1H and 13C NMR spectral analysis of α- and β-d-glucofuranose was performed, including signal assignment, chemical shifts, and coupling constants. Selective and non-selective 1D and 2D NMR experiments were used for the analysis, complemented by spin simulations and iterative spectral analysis.
Highlights
D-glucose is a ubiquitous metabolite in biological systems, and is thereby commonly encountered and studied in fields such as carbohy drate chemistry, metabolomics, and food science
If a sample contains large amounts of glucose and small amounts of other compounds, the concentration of the glucofuranose forms may be comparable to or even higher than that of certain compounds of interest. Such samples may be encountered in e.g. food science, in particular food or beverage quality control, and knowledge about the glucofuranose NMR signals may facilitate the study of low-abundant compounds in these cases
When inspecting the 1H NMR spectrum of D-glucose, minor signals can be observed between 4.07 ppm and 4.32 ppm, i.e. in the area be tween the signals from the pyranose ring protons and anomeric protons, as well as at 5.49 ppm (Fig. 2a)
Summary
D-glucose is a ubiquitous metabolite in biological systems, and is thereby commonly encountered and studied in fields such as carbohy drate chemistry, metabolomics, and food science. To the best of our knowledge, the only 1H NMR data published on the glucofuranoses are the values reported for the anomeric protons [3], meaning that no full NMR characterization of these glucose forms has been carried out This is most likely due to their low abundance and the fact that many of their reso nances are obscured by pyranose signals, especially in 1H NMR. If a sample contains large amounts of glucose and small amounts of other compounds, the concentration of the glucofuranose forms may be comparable to or even higher than that of certain compounds of interest Such samples may be encountered in e.g. food science, in particular food or beverage quality control, and knowledge about the glucofuranose NMR signals may facilitate the study of low-abundant compounds in these cases. The results were obtained using a combination of selective and nonselective 1D and 2D NMR experiments, as well as spin simulations and iterative spectral analysis
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