OXIDATION OF ERYTHROSE SERIES SUGARS BY SODIUM N-CHLOROBENZENESULFONAMIDE IN ALKALINE-MEDIUM - A KINETIC-STUDY

The kinetics of oxidation of D-glucose, D-mannose, D-fructose, D-arabi nose, and D-ribose, with sodium N-chlorobenzenesulphonamide (chloramin e-B or CAB) in alkaline medium have been studied at 35 degrees C and t he rate law, rate = k' [CAB] [Sugar] [OH-](2) is observed. The rate of reaction is influenced by a change in ionic strength of the medium, a nd the dielectric effect is negative. The solvent isotope studies in D 2O show that the rate is almost doubled in heavy water. HPLC and GLC-M S analyses of the products indicated that the erythrose-series sugars are oxidized to a mixture of aldonic acids consisting of arabinonic, r ibonic, erythronic, and glyceric acids in varying proportions. Based o n these data, a mechanism involving the aldoenolic anions of pentoses and keto-enolic anions of hexoses is suggested.