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• W1972415371 abstract "Abstract Recent results point to the existence of an important organometallic chemistry of certain hemoproteins, with the formation of ironcarbon bonds during substrate activation. Evidence for such ironcarbon bond formation comes both from spectroscopic studies on the hemoproteins themselves and from model studies on iron-porphyrins. These ironcarbon bonds are formed either upon reduction or oxidation of several substrates [1]. Reduction of benzylhalides, ArCH2X, by microsomal cytochrome P450 leads to σ-alkyl complexes of this cytochrome involving a Fe(III)CH2Ar bond. Reduction of halothane,CF3CHClBr, leads also to a σ-alkyl cytochrome P450Fe(III)CHClCF3 complexes, whereas microsomal reduction of other polyhalogenated compounds such as CCl4 or CCl3CN leads to ironcarbene complexes, cytochrome P450Fe(II) ← CCl2 (or CClCN). Similar reactions occur upon reduction of the same compounds by iron-porphyrins, the corresponding σ-alkyl or carbene complexes having been isolated and characterized [2]: Cytochrome P450iron(II)carbene complexes are also formed upon metabolic oxidation of the methylene group of 1,3-benzodioxole derivatives, suggesting a mechanism for CH bond activation by cytochrome P450 that involves the intermediate formation of an ironcarbon bond [3]. Very recently, it has been indicated that σ-alkyl (or -aryl) iron(III) complexes of cytochrome P450 [4] or hemoglobin [4, 5] are formed upon metabolic oxidation of various monosubstituted hydrazines by these hemoproteins. Most often, iron(II)diazene complexes are involved as intermediates in this reaction: Similar diazene and σ-alkyl complexes are formed upon reaction of RNHNH2 with ironporphyrins; they have been isolated and characterized [6]. A general scheme for ironcarbon bond formation will be given; it involves a reductive or oxidative activation of the substrate leading to an organic free radical, and the combination of this radical with the hemoproteiniron. Most of these hemoproteinσ-alkyl or carbene complexes have also been detected in vivo; their biological implications will be discussed." @default.
• W1972415371 created "2016-06-24" @default.
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• W1972415371 date "1983-01-01" @default.
• W1972415371 modified "2023-09-26" @default.
• W1972415371 title "Ironcarbon bond formation during substrate activation by hemoproteins" @default.
• W1972415371 cites W1641872032 @default.
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• W1972415371 doi "https://doi.org/10.1016/s0020-1693(00)95027-8" @default.
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