Important role of Fe(III)TPP-oxygen-skatole ternary complex in tryptophan dioxygenase model reaction system

Tajima, Kunihiko; Yoshino, Miwa; Mikami, Kohichi; Edo, Takeshi; Ishizu, Kazuhiko; Ohya-Nishiguchi, Hiroaki

doi:10.1016/s0020-1693(00)80454-5

Cited by 21 publications

(6 citation statements)

References 20 publications

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“…Metal−chelators such as Co(salen), Mn−phthalocyanine, and Co−, Mn−, and Fe−tetraphenylporphyrins − have been shown to serve as models for IDO and TDO as catalysts for dioxygenation of Trp derivatives. The involvement of the ternary complex of O 2 , substrate, and Mn−phthalocyanine as a catalytic intermediate has been demonstrated …”

Section: G Metal−chelate Model Studies For the Two Dioxygenasesmentioning

confidence: 99%

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Heme-Containing Oxygenases

et al. 1996

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Section: G Metal−chelate Model Studies For the Two Dioxygenasesmentioning

confidence: 99%

“…The involvement of the ternary complex of O 2 , substrate, and Mn−phthalocyanine as a catalytic intermediate has been demonstrated , have not yet been established. …”

Section: G Metal−chelate Model Studies For the Two Dioxygenasesmentioning

confidence: 99%

Heme-Containing Oxygenases

et al. 1996

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“…222 In the conversion of 3-methyl indole to o-formamidoacetophenone by Fe ni TPP in the presence of oxygen, an intermediate species was detected by EPR and assigned as the Fe in TPP-OO-substrate complex. 223 Valentine recently reported the nucleophilic oxygen transfer from a bound iron-peroxo ligand to electron-deficient olefins. Peroxo complexes of ferric TPP and TMP porphyrins reacted with enones and quinones to produce the corresponding epoxides.…”

Section: Heme and Pseudo-heme Iron Dioxygen Complexesmentioning

confidence: 99%

Biomimetic Oxygenations Related to Cytochrome P450: Metal-Oxo and Metal-Peroxo Intermediates

McLain

Lee

Groves

2000

Biomimetic Oxidations Catalyzed by Transition Metal Complexes

123

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Oxometalloporphyrin Intermediates in Enzymatic ProcessesMetalloenzymes catalyze a host of biological oxidation reactions that are crucial to life processes. The cytochromes P450, an important family of heme-iron metalloenzymes, are oxidoreductases that activate molecular oxygen (O2) and incorporate one of the oxygen atoms into a wide variety of biological substrates, with concurrent two-electron reduction of the other oxygen atom to H 2 0.' The structure, biochemistry, molecular biology and the chemistry of cytochrome P450 and related model systems was extensively reviewed recently. 1 Cytochrome P450 enzymes have been isolated from numerous mammalian tissues (e.g. liver, kidney, lung, intestine and adrenal cortex), as well as insects, plants, yeast and bacteria, 2 and are known to catalyze hydroxylations, epoxidations, N-, S-and O-dealkylations, N-oxidations, sulfoxidations, and dehalogenations. 1 These oxygenation reactions play a central role in carcinogen activation, drug and xenobiotic detoxification, and steroid and prostaglandin metabolism. Surprisingly, the active site of the enzyme, known in detail from several X-ray crystal structures, is extraordinarily simple, with an iron protoporphyrin IX (3.1; Fig. 3.1) buried deep in a hydrophobic, substrate-binding pocket of 91 Biomimetic Oxidations Catalyzed by Transition Metal Complexes Downloaded from www.worldscientific.com by KAINAN UNIVERSITY on 02/20/15. For personal use only.

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“…Subsequently, Tajima et al prepared peroxoiron(III) complexes by the reaction of H2O2 with the corresponding porphyrin complex (TPP or OEP) and by the reduction of the dioxygen adduct of an iron(II) porphyrin complex and confirmed the accompanying ESR spectral features. [168][169][170][171] The occurrence of two species having the characteristic small anisotropic splitting was explained by assuming different levels of protonation of the bound peroxide.…”

Section: Electron-transfer Pathwaysmentioning

confidence: 99%