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Reactions of carbohydrates with hydroperoxides

1973; Elsevier BV; Volume: 26; Issue: 2 Linguagem: Inglês

10.1016/s0008-6215(00)84515-2

1873-426X

Horace S. Isbell, H.L. Frush, Elizabeth T. Martin,

Enzyme Catalysis and Immobilization

It was found that aqueous alkaline hydrogen peroxide solutions at 0° degrade aldohexoses almost quantitatively to 6 moles of formic acid, and aldopentoses to 5 moles. A mechanism is proposed for the stepwise degradation of aldoses to formic acid, consisting of the addition of a hydroperoxide anion to the aldehydo modification of the sugar, followed by decomposition of the adduct to formic acid and the next lower aldose. The authors found that iron salts accelerate the reaction and suggested that decomposition of the peroxide adduct may take place by a free-radical process, as well as by an ionic mechanism. Reactions of the following hexoses were measured: d-glucose, d-mannose, d-galactose, dD-allose, d-altrose, and d-talose, and the following pentoses: d-xylose, d-arabinose, d-lyxose, and d-ribose. The reaction rates for the various sugars increased in the order just cited.