ESR study of the alkaline degradation of carbohydrates in DMSO. Part 1. Glucose

Abstract

A mechanism for glucose degradation in alkaline media has been proposed based upon ESR spectroscopy studies. This degradative process has been carried out with aqueous Bu₄NOH in dimethyl sulphoxide (DMSO) at room temperature. Several radicals with semidione-like structures are generated during this process, the presence of an α-hydroxycarbonyl group in the molecule being a crucial requisite for the formation of such radicals. Cleavage of the C(3)–C(4) bond, due to a base catalysed retroaldolization is the first step of the degradation. The important role of DMSO in this process as a methylating agent has also been demonstrated. The corresponding hyperfine splittings (hfs) and g-factors of the radicals detected are given.