Selective alkaline oxidative degradation of mono- and di-saccharides by hydrogen peroxide using borate as catalyst and protecting group.
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 H2O2 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 H2O2 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.
van den Berg
R
R
Laboratory of Organic Chemistry and Catalysis, Delft University of Technology, Netherlands.
Peters
J A
JA
van Bekkum
H
H
D001881:Borates / Q000737:chemistry; D002240:Carbohydrate Sequence; D002384:Catalysis; D004187:Disaccharides / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009005:Monosaccharides / Q000737:chemistry*; D010084:Oxidation-Reduction
D001881:Borates; D004187:Disaccharides; D009005:Monosaccharides; D006861:Hydrogen Peroxide