Kinetics and mechanism of oxidation of erythro-series pentoses and hexoses by N-chloro-p-toluenesulfonamide

Kanchugarakoppal S. Rangappa, Manikanahally P. Raghavendra, Dandinasivara S. Mahadevappa, D. Channe Gowda

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    32 Scopus citations

    Abstract

    The kinetics and mechanism of oxidation of D-glucose, D-mannose, D- fructose, D-arabinose, and D-ribose with chloramine-T in alkaline medium were studied. The rate law, rate = k [Chloramine-T] [Sugar] [HO-]2, was observed. The rate of the reaction was influenced by a change in ionic strength of the medium, and the dielectric effect was found to be negative. The latter enabled the computation of d(AB), the size of the activated complex. The reaction rate was almost doubled in deuterium oxide. Activation energies were calculated from the Arrhenius plots. HPLC and GLC-MS analyses of the products indicated that the sugars were oxidized to a mixture of aldonic acids, consisting of arabinonic, ribonic, erythronic, and glyceric acids. Based on these data, a plausible mechanism involving the aldo-enolic anions of pentoses and keto-enolic anions of hexoses is suggested.

    Original languageEnglish (US)
    Pages (from-to)57-67
    Number of pages11
    JournalCarbohydrate Research
    Volume306
    Issue number1-2
    DOIs
    StatePublished - Jan 1998

    All Science Journal Classification (ASJC) codes

    • Analytical Chemistry
    • Biochemistry
    • Organic Chemistry

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