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Oxidation of an indole substrate by porphyrin iron(iii) superoxide: relevance to indoleamine and tryptophan 2,3-dioxygenases

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Abstract

Reaction of FeIII(O2˙)(TPP) with 2,3-dimethylindole at −40 °C gives the ring-opened, dioxygenated N-(2-acetyl-phenyl)-acetamide product. The reaction was monitored in situ by low-temperature UV-vis and 1H NMR spectroscopies. This work demonstrates that a discrete iron(III)(superoxo) porphyrin is competent to carry out indole oxidation, as proposed for the tryptophan and indoleamine 2,3-dioxygenases.

Graphical abstract: Oxidation of an indole substrate by porphyrin iron(iii) superoxide: relevance to indoleamine and tryptophan 2,3-dioxygenases

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Article information


Submitted
27 Dec 2019
Accepted
05 Feb 2020
First published
05 Feb 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Oxidation of an indole substrate by porphyrin iron(III) superoxide: relevance to indoleamine and tryptophan 2,3-dioxygenases

J. J. D. Sacramento and D. P. Goldberg, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC10019A

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