Deamination and decarboxylation of L-thyroxine by Chloroamine-T (CAT) in acidic medium: A mechanistic and kineitc study

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In this manuscript, we report a spectrophotometric study (at 25°C) of oxidation of L-thyroxine by Chloramine T and their mechanistic pathway. The reactions are first-order with respect to both LTX and CAT. Protonated Chloramine-T, TsNHCl, have been suggested as the reactive species of CAT. The Stochiometry of the reaction is 1 : 1. The main products, 2-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl] acetaldehyde was separated, and identified by column chromatography, TLC and FT-IR. The reaction fails to initiate polymerization in the presence of acrylonitrile under the experimental conditions employed. Investigations of the reaction at different temperatures allowed the determination of the activation parameters and a tentative reaction mechanism in good consistency with the kinetic results is discussed.