Cytochrome P450: Structure, Mechanism, and Biochemistry by John T. Groves, Yuan-Zhang Han (auth.), Paul R. Ortiz de

By John T. Groves, Yuan-Zhang Han (auth.), Paul R. Ortiz de Montellano (eds.)

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B) Dolphin. • and Felton. R. • 1974. Biochemical significance of porphyrin 1t cation radicals. Acc. Chern. Res. 7:26-32. Peisach. • Blumberg. W. • Wittenberg. B. • and Wittenberg. 1. • 1968. Electronic structure of protoheme proteins. III. Configuration of the heme and its ligands. J. Bioi. Chern. 243:1871-1880. Loew. G. • Kert. C. I .. Hjelmeland. L. • and Kirchner. R. E. 1977. Active site models of horseradish peroxidase compound I and a cytochrome P-450 analog: Electronic structure and electric field gradients.

Sutherlin, J. • and Lindsey. , 1990, Mechanisms in a biomimetic hydroxylation of a chemical probe: 5-Nitroacenaphthene. J. Org. Chem. 26:6233-6234. (a) Dobson. 1. • Seok, W. • and Meyer. T. • 1986. Epoxidation and catalytic oxidation of olefins based on a RU IV =0IRu II=OH2 couple, Inorg. Chem. 25:1513. (b) Groves. J. T.. Han. Y.. and Van Engen. • 1990, Co-ordination of styrene oxide to a sterically hindered ruthenium(II) porphyrin. J. Chem. Soc. Chem. Commull. 1990:436-437. (a) Ostovic. , and Bruice.

78 Nucleophilic attack of the peroxyacid, in analogy to the putative ferric peroxo species (Fe-OO), at the guanidino carbon of NHA would reasonably give rise to the observed products_ N-hydroxyguanidines afford variously ·NO [with Pb(OAc4) or Fenton's reagent] and HNO (with ferric ion and Pb02). However, the organic product is an N-cyanoamine rather than a urea. The catalytic oxidation of NHA by HRP and microsomal cytochrome P450 has been reported. 79 Both hemeproteins catalyze the formation of citrulline and N0 2, the oxidation product of ·NO.

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