Chiral Discrimination of Monosaccharides Derivatized with 2-Fluorophenyl Hydrazine Using 19F NMR Spectroscopy

Chiral discrimination of monosaccharides holds significant importance, especially given the growing interest of the pharmaceutical industry in their utilization. However, the majority of existing methods has predominantly centered around chromatographic techniques. In this study, we introduce a F-19 NMR-based comprehensive approach for chiral analysis specifically tailored for 15 pairs of aldoses. This technique involves employing sugar hydrazones containing fluorine in combination with chiral octahedral gallium and scandium complexes. By utilizing highly sensitive F-19 NMR spectroscopy, the fluorine label in the sugar hydrazone enables accurate differentiation between d and l enantiomers. The efficiency of the newly developed method was demonstrated through its successful application in both quantitative and qualitative analyses of mixtures containing various monosaccharides.

Automated summary

In this study, a comprehensive chiral analysis method based on F-19 NMR spectroscopy was introduced for accurate differentiation and analysis of monosaccharides. The method utilizes sugar hydrazones with fluorine labels and chiral metal complexes.