Peroxo and oxo intermediates in mononuclear nonheme iron enzymes and related active sites

Solomon, 2000, Geometric and electronic structure/function correlations in non-heme iron enzymes, Chem Rev, 100, 235, 10.1021/cr9900275 Neidig, 2005, Structure–function correlations in oxygen activating non-heme iron enzymes, Chem Commun, 47, 5843, 10.1039/b510233m Price, 2003, The first direct characterization of a high-valent iron intermediate in the reaction of an α-ketoglutarate-dependent dioxygenase: a high-spin Fe(IV) complex in taurine/α-ketoglutarate dioxygenase (TauD) from Escherichia coli, Biochemistry, 42, 7497, 10.1021/bi030011f Riggs-Gelasco, 2004, EXAFS spectroscopic evidence for an FeO unit in the Fe(IV) intermediate observed during oxygen activation by taurine:α-ketoglutarate dioxygenase, J Am Chem Soc, 126, 8108, 10.1021/ja048255q Hoffart, 2006, Direct spectroscopic detection of a C–H-cleaving high-spin Fe(IV) complex in a prolyl-4-hydroxylase, Proc Natl Acad Sci U S A, 103, 14738, 10.1073/pnas.0604005103 Eser, 2007, Direct spectroscopic evidence for a high-spin Fe(IV) intermediate in tyrosine hydroxylase, J Am Chem Soc, 129, 11334, 10.1021/ja074446s Galonic Fujimori, 2007, Two interconverting Fe(IV) intermediates in aliphatic chlorination by the halogenase CytC3, Nat Chem Biol, 3, 113, 10.1038/nchembio856 Galonic Fujimori, 2007, Spectroscopic evidence for a high-spin Br–Fe(IV)–Oxo intermediate in the α-ketoglutarate-dependent halogenase CytC3 from Streptomyces, J Am Chem Soc, 129, 13408, 10.1021/ja076454e Neidig, 2006, Spectroscopic and electronic structure studies of aromatic electrophilic attack and hydrogen-atom abstraction by non-heme iron enzymes, Proc Natl Acad Sci U S A, 103, 12966, 10.1073/pnas.0605067103 Worth, 1993, Isotope effects on the cleavage of DNA by bleomycin—mechanism and modulation, Biochemistry, 32, 2601, 10.1021/bi00061a018 Hecht, 2000, Bleomycin: new perspectives on the mechanism of action, J Nat Prod, 63, 158, 10.1021/np990549f Burger, 1998, Cleavage of nucleic acids by bleomycin, Chem Rev, 98, 1153, 10.1021/cr960438a Petering, 1996, Metallobleomycin–DNA interactions: structures and reactions related to bleomycin-induced DNA damage, Metal Ions Biol Syst, 33, 619 Stubbe, 1996, Bleomycins: a structural model for specificity, binding, and double strand cleavage, Acc Chem Res, 29, 322, 10.1021/ar9501333 Wu, 1985, Mechanism of bleomycin—evidence for a rate-determining 4′-hydrogen abstraction from poly(Da–Du) associated with the formation of both free base and base propenyl, Biochemistry, 24, 7562, 10.1021/bi00347a009 Burger, 2000, Nature of activated bleomycin, Struct Bond, 97, 287, 10.1007/3-540-46592-8_10 Burger, 1981, Activated bleomycin—a transient complex of drug, iron, and oxygen that degrades DNA, J Biol Chem, 256, 1636, 10.1016/S0021-9258(19)68452-8 Sugiura, 1980, Bleomycin–iron complexes—electron-spin resonance study, ligand effect, and implication for action mechanism, J Am Chem Soc, 102, 5208, 10.1021/ja00536a015 Veselov, 1995, Iron coordination of activated bleomycin probed by Q- and X-band ENDOR—hyperfine coupling to activated 17O oxygen, 14N and exchangeable 1H, J Am Chem Soc, 117, 7508, 10.1021/ja00133a023 Burger, 1983, Mössbauer study of iron bleomycin and its activation intermediates, J Biol Chem, 258, 1559, 10.1016/S0021-9258(18)33020-5 Veselov, 1998, Q-band electron nuclear double resonance of ferric bleomycin and activated bleomycin complexes with DNA: Fe(III) hyperfine interaction with P-31 and DNA-induced perturbation to bleomycin structure, J Am Chem Soc, 120, 1030, 10.1021/ja972138w Sam, 1994, Electrospray mass spectrometry of iron bleomycin: demonstration that activated bleomycin is a ferric peroxide complex, J Am Chem Soc, 116, 3250, 10.1021/ja00091a032 Westre, 1995, Determination of the geometric and electronic structure of activated bleomycin using X-ray-absorption spectroscopy, J Am Chem Soc, 117, 1309, 10.1021/ja00109a014 Neese, 2000, Electronic structure of activated bleomycin: oxygen intermediates in heme versus non-heme iron, J Am Chem Soc, 122, 11703, 10.1021/ja001812y Kovaleva, 2007, Crystal structures of Fe2+ dioxygenase superoxo, alkylperoxo, and bound product intermediates, Science, 316, 453, 10.1126/science.1134697 Karlsson, 2003, Crystal structure of naphthalene dioxygenase: side-on binding of dioxygen to iron, Science, 299, 1039, 10.1126/science.1078020 Pau, 2007, Substrate activation for O2 reactions by oxidized metal centers in biology, Proc Natl Acad Sci U S A, 104, 18355, 10.1073/pnas.0704191104 Solomon, 2003, Non-heme iron enzymes: contrasts to heme catalysis, Proc Natl Acad Sci U S A, 100, 3589, 10.1073/pnas.0336792100 Cheesman, 1991, Magnetic circular dichroism of hemoproteins, Adv Inorg Chem, 36, 201, 10.1016/S0898-8838(08)60040-9 Lehnert, 2001, Electronic structure of high-spin iron(III)–alkylperoxo complexes and its relation to low-spin analogues: reaction coordinate of O–O bond homolysis, J Am Chem Soc, 123, 12802, 10.1021/ja011450+ Lehnert, 2001, Spectroscopic properties and electronic structure of low-spin Fe(III)–alkylperoxo complexes: homolytic cleavage of the O–O bond, J Am Chem Soc, 123, 8271, 10.1021/ja010165n Lehnert, 2002, Electronic structure and reactivity of low-spin Fe(III)–hydroperoxo complexes: comparison to activated bleomycin, J Am Chem Soc, 124, 10810, 10.1021/ja012621d Decker, 2006, Direct hydrogen-atom abstraction by activated bleomycin: an experimental and computational study, J Am Chem Soc, 128, 4719, 10.1021/ja057378n Kumar, 2006, Proton-shuffle mechanism of O–O activation for formation of a high-valent oxo–iron species of bleomycin, J Am Chem Soc, 128, 16148, 10.1021/ja064611o Chow, 2008, Further insights into the mechanism of the reaction of activated bleomycin with DNA, Proc Natl Acad Sci U S A, 105, 13241, 10.1073/pnas.0806378105 Rohde, 2003, Crystallographic and spectroscopic characterization of a nonheme Fe(IV)O complex, Science, 299, 1037, 10.1126/science.299.5609.1037 Kaizer, 2004, Nonheme FeIVO complexes that can oxidize the C–H bonds of cyclohexane at room temperature, J Am Chem Soc, 126, 472, 10.1021/ja037288n Klinker, 2005, Structures of nonheme oxoiron(IV) complexes from X-ray crystallography, NMR spectroscopy, and DFT calculations, Angew Chem Int Ed, 44, 3690, 10.1002/anie.200500485 Hirao, 2008, A two-state reactivity rationale for counterintuitive axial ligand effects on the CH activation reactivity of nonheme FeIVO oxidants, Chem Eur J, 14, 1740, 10.1002/chem.200701739 Hirao, 2006, Two-state reactivity in alkane hydroxylation by non-heme iron–oxo complexes, J Am Chem Soc, 128, 8590, 10.1021/ja061609o Sastri, 2007, Axial ligand tuning of a nonheme iron(IV)–oxo unit for hydrogen atom abstraction, Proc Natl Acad Sci U S A, 104, 19181, 10.1073/pnas.0709471104 Decker, 2004, Spectroscopic and quantum chemical characterization of the electronic structure and bonding in a non-heme FeIVO complex, J Am Chem Soc, 126, 5378, 10.1021/ja0498033 Decker, 2007, Spectroscopic and quantum chemical studies on low-spin FeIVO complexes: FeO bonding and its contributions to reactivity, J Am Chem Soc, 129, 15983, 10.1021/ja074900s Rüffer, 2000, Nuclear inelastic scattering, Hyperfine Interact, 128, 255, 10.1023/A:1012643918108 Scheidt, 2005, Nuclear resonance vibrational spectroscopy—NRVS, J Inorg Biochem, 99, 60, 10.1016/j.jinorgbio.2004.11.004 Sturhahn, 2004, Nuclear resonant spectroscopy, J Phys Condens Matter, 16, S497, 10.1088/0953-8984/16/5/009 Bell, 2008, A combined NRVS and DFT study of FeIVO model complexes: a diagnostic method for the elucidation of non-heme iron enzyme intermediates, Angew Chem Int Ed, 47, 9071, 10.1002/anie.200803740 Decker, 2006, Spectroscopy and electronic structures of mono- and binuclear high-valent non-heme iron–oxo systems, J Inorg Biochem, 100, 697, 10.1016/j.jinorgbio.2006.01.013