Oxidation of an indole substrate by porphyrin iron(iii) superoxide: relevance to indoleamine and tryptophan 2,3-dioxygenases.
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ABSTRACT:
SUBMITTER: Sacramento JJD
PROVIDER: S-EPMC7065957 | biostudies-literature | 2020 Mar
REPOSITORIES: biostudies-literature
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Oxidation of an indole substrate by porphyrin iron(iii) superoxide: relevance to indoleamine and tryptophan 2,3-dioxygenases.
Sacramento Jireh Joy D JJD Goldberg David P DP
Chemical communications (Cambridge, England) 20200301 20
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. ...[more]
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