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

Abstract

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 19F 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 19F 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.