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Volumn 4, Issue 12, 2012, Pages 1024-1029

An N-bridged high-valent diiron-oxo species on a porphyrin platform that can oxidize methane

Author keywords

[No Author keywords available]

Indexed keywords

3 CHLOROPERBENZOIC ACID; 3-CHLOROPERBENZOIC ACID; CHLOROBENZOIC ACID DERIVATIVE; METALLOPORPHYRIN; METHANE; NITROGEN;

EID: 84870177110     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1471     Document Type: Article
Times cited : (133)

References (43)
  • 1
    • 77349091080 scopus 로고    scopus 로고
    • Hydrocarbon hydroxylation by cytochrome P450 enzymes
    • Ortiz de Montellano, P. R. Hydrocarbon hydroxylation by cytochrome P450 enzymes. Chem. Rev. 110, 932-948 (2010).
    • (2010) Chem. Rev. , vol.110 , pp. 932-948
    • Ortiz De Montellano, P.R.1
  • 2
    • 0011697055 scopus 로고
    • Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage
    • Meunier, B. Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage. Chem. Rev. 92, 1411-1456 (1992).
    • (1992) Chem. Rev. , vol.92 , pp. 1411-1456
    • Meunier, B.1
  • 3
    • 0035800409 scopus 로고    scopus 로고
    • Dioxygen activation and methane hydroxylation by soluble methane monooxygenase: A tale of two irons and three proteins
    • Merkx, M. et al. Dioxygen activation and methane hydroxylation by soluble methane monooxygenase: a tale of two irons and three proteins. Angew. Chem. Int. Ed. 40, 2782-2807 (2001).
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2782-2807
    • Merkx, M.1
  • 4
    • 20744447134 scopus 로고    scopus 로고
    • Hydroxylation of C-H bonds at carboxylate-bridged diiron centres
    • Lippard, S. J. Hydroxylation of C-H bonds at carboxylate-bridged diiron centres. Phil. Trans. R. Soc. A 363, 861-877 (2005).
    • (2005) Phil. Trans. R. Soc. A , vol.363 , pp. 861-877
    • Lippard, S.J.1
  • 5
    • 0037560872 scopus 로고    scopus 로고
    • Mechanistic studies on the hydroxylation of methane by methane monooxygenase
    • Baik, M-H., Newcomb, M., Friesner, R. A. & Lippard, S. J. Mechanistic studies on the hydroxylation of methane by methane monooxygenase. Chem. Rev. 103, 2385-2419 (2003).
    • (2003) Chem. Rev. , vol.103 , pp. 2385-2419
    • Baik, M.-H.1    Newcomb, M.2    Friesner, R.A.3    Lippard, S.J.4
  • 6
    • 1542348939 scopus 로고    scopus 로고
    • Synthetic models for non-heme carboxylate-bridged diiron metalloproteins: Strategies and tactics
    • Tshuva, E. Y. & Lippard, S. J. Synthetic models for non-heme carboxylate-bridged diiron metalloproteins: strategies and tactics. Chem. Rev. 104, 987-1012 (2004).
    • (2004) Chem. Rev. , vol.104 , pp. 987-1012
    • Tshuva, E.Y.1    Lippard, S.J.2
  • 7
    • 77954913417 scopus 로고    scopus 로고
    • Current challenges of modeling diiron enzyme active sites for dioxygen activation by biomimetic synthetic complexes
    • Friedle, S., Reisner, E. & Lippard, S. J. Current challenges of modeling diiron enzyme active sites for dioxygen activation by biomimetic synthetic complexes. Chem. Soc. Rev. 39, 2768-2779 (2010).
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 2768-2779
    • Friedle, S.1    Reisner, E.2    Lippard, S.J.3
  • 8
    • 33645885635 scopus 로고    scopus 로고
    • Structure and mechanism in the bacterial dihaem cytochrome c peroxidases
    • Pettigrew, G. W., Echalier, A. & Pauleta, S. R. Structure and mechanism in the bacterial dihaem cytochrome c peroxidases. J. Inorg. Biochem. 100, 551-567 (2006).
    • (2006) J. Inorg. Biochem. , vol.100 , pp. 551-567
    • Pettigrew, G.W.1    Echalier, A.2    Pauleta, S.R.3
  • 9
    • 47249161981 scopus 로고    scopus 로고
    • A catalytic di-heme Bis-Fe(IV) intermediate alternative to an Fe(IV)=O porphyrin radical
    • Li, X. et al. A catalytic di-heme bis-Fe(IV) intermediate, alternative to an Fe(IV)=O porphyrin radical. Proc. Natl Acad. Sci. USA 105, 8597-8600 (2008).
    • (2008) Proc. Natl Acad. Sci. USA , vol.105 , pp. 8597-8600
    • Li, X.1
  • 10
    • 77949400738 scopus 로고    scopus 로고
    • Crystallo posttranslational modification within a MauG/pre-methylamine dehydrogenase complex
    • Jensen, L. M. R., Sanishvili, R., Davidson, V. L. & Wilmot, C. M. In crystallo posttranslational modification within a MauG/pre-methylamine dehydrogenase complex. Science 327, 1392-1394 (2010).
    • (2010) Science , vol.327 , pp. 1392-1394
    • Jensen, L.M.R.1    Sanishvili, R.2    Davidson, V.L.3    Wilmot, C.M.4
  • 11
    • 44349133404 scopus 로고    scopus 로고
    • Bio-inspired oxidation of methane in water catalyzed by N-bridged diiron phthalocyanine complex
    • Sorokin, A. B., Kudrik, E. V. & Bouchu, D. Bio-inspired oxidation of methane in water catalyzed by N-bridged diiron phthalocyanine complex. Chem. Commun. 2562-2564 (2008).
    • (2008) Chem. Commun. , pp. 2562-2564
    • Sorokin, A.B.1    Kudrik, E.V.2    Bouchu, D.3
  • 12
    • 78049260508 scopus 로고    scopus 로고
    • Oxidation of methane and ethylene in water at ambient conditions
    • Sorokin, A. B. et al. Oxidation of methane and ethylene in water at ambient conditions. Catal. Today 157, 149-154 (2010).
    • (2010) Catal. Today , vol.157 , pp. 149-154
    • Sorokin, A.B.1
  • 13
    • 53849118154 scopus 로고    scopus 로고
    • N-bridged diiron phthalocyanine catalyzes oxidation of benzene with H2O2 via benzene oxide with NIH shift evidenced by using 1,3,5-[D3]benzene as a probe
    • Kudrik, E. V. & Sorokin, A. B. N-bridged diiron phthalocyanine catalyzes oxidation of benzene with H2O2 via benzene oxide with NIH shift evidenced by using 1,3,5-[D3]benzene as a probe. Chem. Eur. J. 14, 7123-7126 (2008).
    • (2008) Chem. Eur. J. , vol.14 , pp. 7123-7126
    • Kudrik, E.V.1    Sorokin, A.B.2
  • 14
    • 70049098754 scopus 로고    scopus 로고
    • Preparation and characterization of m-nitrido diiron phthalocyanines with electron-withdrawing substituents: Application for catalytic aromatic oxidation
    • Isci, U. et al. Preparation and characterization of m-nitrido diiron phthalocyanines with electron-withdrawing substituents: application for catalytic aromatic oxidation. Dalton Trans. 7410-7420 (2009).
    • (2009) Dalton Trans. , pp. 7410-7420
    • Isci, U.1
  • 15
    • 71049125365 scopus 로고    scopus 로고
    • Stable N-bridged diiron(IV) phthalocyanine cation radical complexes: Synthesis and properties
    • Afanasiev, P., Bouchu, D., Kudrik, E. V., Millet, J-M. M. & Sorokin, A. B. Stable N-bridged diiron(IV) phthalocyanine cation radical complexes: synthesis and properties. Dalton Trans. 9828-9836 (2009).
    • (2009) Dalton Trans. , pp. 9828-9836
    • Afanasiev, P.1    Bouchu, D.2    Kudrik, E.V.3    Millet, J.-M.M.4    Sorokin, A.B.5
  • 16
    • 78650725873 scopus 로고    scopus 로고
    • High-valent diiron species generated from N-bridged diiron phthalocyanine and H2O2
    • Afanasiev, P., Kudrik, E. V., Millet, J-M. M., Bouchu, D. & Sorokin, A. B. High-valent diiron species generated from N-bridged diiron phthalocyanine and H2O2. Dalton Trans. 40, 701-710 (2011).
    • (2011) Dalton Trans. , vol.40 , pp. 701-710
    • Afanasiev, P.1    Kudrik, E.V.2    Millet, J.-M.M.3    Bouchu, D.4    Sorokin, A.B.5
  • 17
    • 33845557435 scopus 로고
    • High-valent iron-porphyrin complexes related to peroxidase and cytochrome P-450
    • Groves, J. T., Haushalter, R. C., Nakamura, M., Nemo, T. E. & Evans, B. J. High-valent iron-porphyrin complexes related to peroxidase and cytochrome P-450. J. Am. Chem. Soc. 103, 2884-2886 (1981).
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 2884-2886
    • Groves, J.T.1    Haushalter, R.C.2    Nakamura, M.3    Nemo, T.E.4    Evans, B.J.5
  • 18
    • 0034731869 scopus 로고    scopus 로고
    • Generation of oxoiron(IV) tetramesitylporphyrin p-cation radical complexes by m-CPBA oxidation of ferric tetramesitylporphyrin derivatives in butyronitrile at 278 8C. Evidence for the formation of sixcoordinate oxoiron(IV) tetramesitylporphyrin p-cation radical complexes Fe(IV)=O(tmp)X (X=Cl2, Br2), by Mössbauer and X-ray absorption spectroscopy
    • Wolter, T. et al. Generation of oxoiron(IV) tetramesitylporphyrin p-cation radical complexes by m-CPBA oxidation of ferric tetramesitylporphyrin derivatives in butyronitrile at 278 8C. Evidence for the formation of sixcoordinate oxoiron(IV) tetramesitylporphyrin p-cation radical complexes Fe(IV)=O(tmp)X (X=Cl2, Br2), by Mössbauer and X-ray absorption spectroscopy. J. Inorg. Biochem. 78, 117-122 (2000).
    • (2000) J. Inorg. Biochem. , vol.78 , pp. 117-122
    • Wolter, T.1
  • 19
    • 39749096483 scopus 로고    scopus 로고
    • Direct evidence for an iron(IV) oxo porphyrin p-cation radical as an active oxidant in catalytic oxygenation reactions
    • Han, A-R. et al. Direct evidence for an iron(IV)-oxo porphyrin p-cation radical as an active oxidant in catalytic oxygenation reactions. Chem. Commun. 1076-1078 (2008).
    • (2008) Chem. Commun. , pp. 1076-1078
    • Han, A.-R.1
  • 20
    • 48149083506 scopus 로고    scopus 로고
    • Which oxidant is really responsible for P450 model oxygenation reactions? A kinetic approach
    • Franke, A., Fertinger, C. & van Eldik, R. Which oxidant is really responsible for P450 model oxygenation reactions? A kinetic approach. Angew. Chem. Int. Ed. 47, 5238-5242 (2008).
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5238-5242
    • Franke, A.1    Fertinger, C.2    Van Eldik, R.3
  • 21
    • 67650501146 scopus 로고    scopus 로고
    • A highly reactive P450 model compound i
    • Bell, S. R. & Groves, J. T. A highly reactive P450 model compound I. J. Am. Chem. Soc. 131, 9640-9641 (2009).
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 9640-9641
    • Bell, S.R.1    Groves, J.T.2
  • 22
    • 84861609137 scopus 로고    scopus 로고
    • Generation and characterization of high-valent iron oxo phthalocyanines
    • Afanasiev, P. et al. Generation and characterization of high-valent iron oxo phthalocyanines. Chem. Commun. 48, 6088-6090 (2012).
    • (2012) Chem. Commun. , vol.48 , pp. 6088-6090
    • Afanasiev, P.1
  • 23
    • 79957845133 scopus 로고    scopus 로고
    • A mononuclear non-heme iron(IV)-oxo complex which is more reactive than cytochrome P450 model compound i
    • Seo, M. S. et al. A mononuclear non-heme iron(IV)-oxo complex which is more reactive than cytochrome P450 model compound I. Chem. Sci. 2, 1039-1045 (2011).
    • (2011) Chem. Sci. , vol.2 , pp. 1039-1045
    • Seo, M.S.1
  • 24
    • 0017319319 scopus 로고
    • Metal-metal interactions involving metalloporphyrins. III. Conversion of tetraphenylporphinatoiron III) azide to an N-bridged hemin dimer
    • Summerville, D. A. & Cohen, I. A. Metal-metal interactions involving metalloporphyrins. III. Conversion of tetraphenylporphinatoiron(III) azide to an N-bridged hemin dimer. J. Am. Chem. Soc. 98, 1747-1752 (1976).
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 1747-1752
    • Summerville, D.A.1    Cohen, I.A.2
  • 25
    • 84940901422 scopus 로고    scopus 로고
    • (eds Kadish, K. M., Smith, K. M. & Guilard, R.) Elsevier
    • Floris, B., Donzello, M. P. & Ercolani, C. in The Porphyrin Handbook Vol. 18 (eds Kadish, K. M., Smith, K. M. & Guilard, R.) 1-62 (Elsevier, 2003).
    • (2003) The Porphyrin Handbook , vol.18 , pp. 1-62
    • Floris, B.1    Donzello, M.P.2    Ercolani, C.3
  • 26
    • 0001877970 scopus 로고
    • Iron-containing proteins and related analogs - Complementary Mössbauer, EPR and magnetic susceptibility studies in Bioinorganic Chemistry
    • Springer
    • Trautwein, A. X., Bill, E., Bominaar, E. L. & Winkler, H. Iron-containing proteins and related analogs - complementary Mössbauer, EPR and magnetic susceptibility studies in Bioinorganic Chemistry 1-95 (Structure and Bonding Series 78, Springer, 1991).
    • (1991) Structure and Bonding Series , vol.78 , pp. 1-95
    • Trautwein, A.X.1    Bill, E.2    Bominaar, E.L.3    Winkler, H.4
  • 27
    • 0001228121 scopus 로고
    • Interaction of dioxygen with binuclear nitride-bridged iron porphyrins
    • Bocian, D. F. et al. Interaction of dioxygen with binuclear nitride-bridged iron porphyrins. Inorg. Chem. 23, 800-807 (1984).
    • (1984) Inorg. Chem. , vol.23 , pp. 800-807
    • Bocian, D.F.1
  • 28
    • 33845552180 scopus 로고
    • Mössbauer spectra of oxidized iron porphyrins
    • English, D. R., Hendrickson, D. N. & Suslick, K. S. Mössbauer spectra of oxidized iron porphyrins. Inorg. Chem. 22, 367-368 (1983).
    • (1983) Inorg. Chem. , vol.22 , pp. 367-368
    • English, D.R.1    Hendrickson, D.N.2    Suslick, K.S.3
  • 29
    • 78650685100 scopus 로고    scopus 로고
    • Molecular and electronic structures of dinuclear iron complexes incorporating strongly electron-donating ligands: Implications for the generation of the one- and two-electron oxidized forms
    • Strautmann, J. B. H. et al. Molecular and electronic structures of dinuclear iron complexes incorporating strongly electron-donating ligands: implications for the generation of the one- and two-electron oxidized forms. Inorg. Chem. 50, 155-171 (2011).
    • (2011) Inorg. Chem. , vol.50 , pp. 155-171
    • Strautmann, J.B.H.1
  • 30
    • 0002455044 scopus 로고
    • The ideal Mössbauer effect absorber thickness
    • Long, G. J., Cranshaw, T. E. & Longworth, G. The ideal Mössbauer effect absorber thickness. MERDJ 6, 42-49 (1983).
    • (1983) MERDJ , vol.6 , pp. 42-49
    • Long, G.J.1    Cranshaw, T.E.2    Longworth, G.3
  • 31
    • 0006532989 scopus 로고
    • (m-Nitrido)bis[5101520- tetraphenylporphyrinato)iron](2+) an iron(IV) porphyrin p-radical cation
    • English, D. R., Hendrickson, D. N. & Suslick, K. S. (m-Nitrido)bis[(5,10,15,20- tetraphenylporphyrinato)iron](2+), an iron(IV) porphyrin p-radical cation. Inorg. Chem. 24, 121-122 (1985).
    • (1985) Inorg Chem , vol.24 , pp. 121-122
    • English, D.R.1    Hendrickson, D.N.2    Suslick, K.S.3
  • 32
    • 0001581893 scopus 로고
    • Oxoferryl complexes of the halogenated (porphyrinato)iron catalyst: (tetrakis(2,6-dichlorophenyl)porphyrinato)iron
    • Gold, A. et al. Oxoferryl complexes of the halogenated (porphyrinato)iron catalyst: (tetrakis(2,6-dichlorophenyl)porphyrinato)iron. J. Am. Chem. Soc. 110, 5756-5761 (1988).
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5756-5761
    • Gold, A.1
  • 33
    • 0025307822 scopus 로고
    • Evidence for variable metal-radical spin coupling in oxoferrylporphyrin cation radical complexes
    • Bill, E. et al. Evidence for variable metal-radical spin coupling in oxoferrylporphyrin cation radical complexes. Eur. J. Biochem. 188, 665-672 (1990).
    • (1990) Eur. J. Biochem. , vol.188 , pp. 665-672
    • Bill, E.1
  • 34
    • 0001393113 scopus 로고
    • Models for peroxidase compound I: Generation and spectroscopic characterization of new oxoferrylporphyrin p-cation radical species
    • Mandon, D. et al. Models for peroxidase compound I: generation and spectroscopic characterization of new oxoferrylporphyrin p-cation radical species. Inorg. Chem. 31, 4404-4409 (1992).
    • (1992) Inorg. Chem. , vol.31 , pp. 4404-4409
    • Mandon, D.1
  • 35
    • 0039725130 scopus 로고    scopus 로고
    • The molecular and electronic structure of symmetrically and asymmetrically coordinated, non-heme iron complexes containing [Fe(III) m-N)Fe(IV)]4+ (S = 3/2) and [Fe(IV)(m-N)FeIV)]5+ (S = 0) cores
    • Jüstel, T. et al. The molecular and electronic structure of symmetrically and asymmetrically coordinated, non-heme iron complexes containing [Fe(III)(m-N)Fe(IV)]4+ (S = 3/2) and [Fe(IV)(m-N)Fe(IV)]5+ (S = 0) cores. Chem. Eur. J. 5, 793-810 (1999).
    • (1999) Chem. Eur. J. , vol.5 , pp. 793-810
    • Jüstel, T.1
  • 36
    • 33748222041 scopus 로고
    • M-Nitridodiiron complexes with asymmetric [Fe(IV); N-Fe(III)]4+ and symmetric [Fe(IV)=N=FeIV)]5+ structural elements
    • Jüstel, T. et al. m-Nitridodiiron complexes with asymmetric [Fe(IV);N-Fe(III)]4+ and symmetric [Fe(IV)=N=Fe(IV)]5+ structural elements. Angew. Chem. Int. Ed. Engl. 34, 669-672 (1995).
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 669-672
    • Jüstel, T.1
  • 37
    • 34547732579 scopus 로고    scopus 로고
    • The road to non-heme oxoferryls and beyond
    • Que, L. Jr The road to non-heme oxoferryls and beyond. Acc. Chem. Res. 40, 493-500 (2007).
    • (2007) Acc. Chem. Res. , vol.40 , pp. 493-500
    • Que Jr., L.1
  • 38
    • 0006966776 scopus 로고
    • Spin-coupling in distorted high-valent FeIV)-orphyrin radical complexes
    • Müther, M. et al. Spin-coupling in distorted high-valent Fe(IV)-porphyrin radical complexes. Hyperfine Interact. 91, 803-808 (1994).
    • (1994) Hyperfine Interact. , vol.91 , pp. 803-808
    • Müther, M.1
  • 39
    • 0001349992 scopus 로고
    • Intramolecular kinetic isotope effects in alkane hydroxylations catalyzed by manganese and iron porphyrin complexes
    • Sorokin, A., Robert, A. & Meunier, B. Intramolecular kinetic isotope effects in alkane hydroxylations catalyzed by manganese and iron porphyrin complexes. J. Am. Chem. Soc. 115, 7293-7299 (1993).
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 7293-7299
    • Sorokin, A.1    Robert, A.2    Meunier, B.3
  • 40
    • 20044363984 scopus 로고    scopus 로고
    • Catalytically active m-oxodiiron IV) oxidants from iron(III) and dioxygen
    • Ghosh, A. et al. Catalytically active m-oxodiiron(IV) oxidants from iron(III) and dioxygen. J. Am. Chem. Soc. 127, 2505-2513 (2005).
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 2505-2513
    • Ghosh, A.1
  • 41
  • 42
    • 77951693360 scopus 로고    scopus 로고
    • Million-fold activation of the [Fe2(m-O)2] diamond core for C-H bond cleavage
    • Xue, G., De Hont, R., Münck, E. & Que, L. Jr Million-fold activation of the [Fe2(m-O)2] diamond core for C-H bond cleavage. Nature Chem. 2, 400-405 (2010).
    • (2010) Nature Chem. , vol.2 , pp. 400-405
    • Xue, G.1    De Hont, R.2    Münck, E.3    Que Jr., L.4
  • 43
    • 80055035379 scopus 로고    scopus 로고
    • Selective C-H oxidation catalyzed by metalloporphyrins
    • Costas, M. Selective C-H oxidation catalyzed by metalloporphyrins. Coord. Chem. Rev. 255, 2912-2932 (2011).
    • (2011) Coord. Chem. Rev. , vol.255 , pp. 2912-2932
    • Costas, M.1


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