Selective alkaline oxidative degradation of mono- and di-saccharides by hydrogen peroxide using borate as catalyst and protecting group

Abstract

Lactose, maltose, cellobiose, and galactose can be degraded selectively in one step and in high yield into the corresponding next lower aldose and formic acid by H 2O 2 in the presence of borate. The selectivity further improves when a small amount of EDTA is added, in order to suppress the influence of transition metal ions which catalyze the decomposition of H 2O 2 via radical pathways, leading to non-selective oxidative degradation of aldoses. The function of borate in the selective oxidative degradation of aldoses is two-fold: catalysis of the degradation of the starting aldose and protection of the next lower aldose against oxidation.