INTERACTION OF (1->4)- AND (1->6)-LINKED DISSACHARIDES WITH THE FENTON REAGENT UNDER PHYSIOLOGICAL CONDITIONS

Article abstract of DOI:10.1016/S0008-6215(00)90805-X

Reactions of (1->4) and (1->6)-linked disaccharides, mainly of maltose and isomaltose, with the Fenton reagent under physiologigal conditions were studied.Chemical characterization of oxidation products was conducted by g.l.c. and g.l.c.-m.s. of their trimethylsilyl derivatives, and the results demonstrated that (1->6)-linked disaccharides are more reactive with the hydroxyl radical (.OH) generated by the Fenton reagent than (1->4)-linked disaccharides.About 35-40percent of (1->6)- and 15-20percent of (1->4)-linked disaccharides were oxydatively degraded to smaller molecules after incubation for 24 h.Of the four disaccharides examined, namely, maltose, isomaltose, cellobiose, and gentiobiose, the α-(1->6)-linked disaccharide isomaltose exhibited the highest reactivity, whereas the β-(1->4)-linked disaccharide cellobiose showed the lowest.These results suggest the exisence of the a relationship between the configuration of the glycosidic linkage and the reactivity with .OH in aqueous solution.