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Electrochemical and peroxidase O2-mediated oxidation of indole-3-acetic acid at physiological pH by Tao Hu; Glenn Dryhurst is a Engineering article available to read on EtoBox.

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Indolc~3~acetic ackl (IAA) or an oxid:tfi,/e metabolilc is believed to be a growth hormone in plants. IAA is also fl~und in |lie mammalian central nervous system althou3h ils biological roles, if any, are presently unknown. In tills investigation file electrochemically driven and peroxidase/Oaomediate:l oxida,ion chemistry of IAA at physiological pH has been studied with the primary goal of identifying the major reaction products. Based ~lpon the nature o! these products it has been concluded that, at pH 7.4, the anion of IAA is initially oxidized (one-electron) to an acetox,/ radical that in part undergoes a second one-electron oxidation/decarboxylation to a carbocation precursor of 3-hydroxymethyl-2-oxindole (1), indole-3~carbinol (13) and 3-methylene-2-oxindole (3). lndole-3-carbinol ( ) can be fitrther oxidized (2e, ! H + ) to the cation of 3-hydroxymethylene indolenine, the precursor of indole-3-aldehyd¢ (2), 3-hydroxy-2oxidole (8) and 3,3-dihydroxy-2-oxindole (12). Direct decarbo~ylation of the initial acetoxy radical yields a carbon-centered radical that rapidly dimerizes to a compound dmt is further oxidized to 3,3'41,2oethanediyl)his-I H-indolo2-ol (9) and thence 5,7.12,13

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Author

Tao Hu; Glenn Dryhurst

Publisher

Elsevier ; Elsevier BV (ISSN 1572-6657)

Published

1997

Language

EN

Field

Engineering (Physical Sciences)