Ferryl Protonation in Oxoiron(IV) Porphyrins and Its Role in Oxygen Transfer

Boaz, Nicholas C.; Bell, Seth R.; Groves, John T.

doi:10.1021/ja508759t

Title: Ferryl Protonation in Oxoiron(IV) Porphyrins and Its Role in Oxygen Transfer

Journal Article · Tue Feb 17 00:00:00 EST 2015 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja508759t· OSTI ID:1385431

Boaz, Nicholas C. ^[1]; Bell, Seth R. ^[1]; Groves, John T. ^[1]

Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States

Cite

Export

Save

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Catalytic Hydrocarbon Functionalization (CCHF)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

DOE Contract Number:: SC0001298

OSTI ID:: 1385431

Journal Information:: Journal of the American Chemical Society, Vol. 137, Issue 8; Related Information: CCHF partners with University of Virginia (lead); Brigham Young University; California Institute of Technology; Colorado School of Mines; University of Maryland; University of North Carolina, Chapel Hill; University of North Texas; Princeton University; The Scripps Research Institute; Yale University; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (85)

A Highly Reactive P450 Model Compound I Bell, Seth R.; Groves, John T. Journal of the American Chemical Society, Vol. 131, Issue 28 https://doi.org/10.1021/ja903394s	journal	July 2009
Brønsted Acid-Promoted C–H Bond Cleavage via Electron Transfer from Toluene Derivatives to a Protonated Nonheme Iron(IV)-Oxo Complex with No Kinetic Isotope Effect Park, Jiyun; Lee, Yong-Min; Nam, Wonwoo Journal of the American Chemical Society, Vol. 135, Issue 13 https://doi.org/10.1021/ja311662w	journal	March 2013
Does Hydrogen-Bonding Donation to Manganese(IV)-Oxo and Iron(IV)-Oxo Oxidants Affect the Oxygen-Atom Transfer Ability? A Computational Study Latifi, Reza; Sainna, Mala A.; Rybak-Akimova, Elena V. Chemistry - A European Journal, Vol. 19, Issue 12 https://doi.org/10.1002/chem.201202811	journal	January 2013
Proton-Promoted Oxygen Atom Transfer vs Proton-Coupled Electron Transfer of a Non-Heme Iron(IV)-Oxo Complex Park, Jiyun; Morimoto, Yuma; Lee, Yong-Min Journal of the American Chemical Society, Vol. 134, Issue 8 https://doi.org/10.1021/ja211641s	journal	February 2012
Effects of the electron-withdrawing power of substituents on the electronic structure and reactivity in oxoiron(IV) porphyrin .pi.-cation radical complexes Fujii, Hiroshi Journal of the American Chemical Society, Vol. 115, Issue 11 https://doi.org/10.1021/ja00064a027	journal	June 1993
Setting an Upper Limit on the Myoglobin Iron(IV)Hydroxide p K _a : Insight into Axial Ligand Tuning in Heme Protein Catalysis Yosca, Timothy H.; Behan, Rachel K.; Krest, Courtney M. Journal of the American Chemical Society, Vol. 136, Issue 25 https://doi.org/10.1021/ja503588n	journal	June 2014
Theoretical studies on concerted versus two steps hydrogen atom transfer reaction by non-heme MnIV/IIIO complexes: how important is the oxo ligand basicity in the C–H activation step? Jaccob, Madhavan; Ansari, Azaj; Pandey, Bhawana Dalton Transactions, Vol. 42, Issue 47 https://doi.org/10.1039/c3dt52290c	journal	January 2013
Mechanisms of Peroxynitrite Decomposition Catalyzed by FeTMPS, a Bioactive Sulfonated Iron Porphyrin Shimanovich, Roman; Groves, John T. Archives of Biochemistry and Biophysics, Vol. 387, Issue 2 https://doi.org/10.1006/abbi.2000.2247	journal	March 2001
Unified View of Oxidative C–H Bond Cleavage and Sulfoxidation by a Nonheme Iron(IV)–Oxo Complex via Lewis Acid-Promoted Electron Transfer Park, Jiyun; Morimoto, Yuma; Lee, Yong-Min Inorganic Chemistry, Vol. 53, Issue 7 https://doi.org/10.1021/ic403124u	journal	March 2014
Mechanistic Consequences of Chiral Radical Clock Probes: Analysis of the Mononuclear Non-Heme Iron Enzyme HppE with 2-Hydroxy-3-methylenecyclopropyl Radical Clock Substrates Huang, Hui; Chang, Wei-Chen; Lin, Geng-Min Journal of the American Chemical Society, Vol. 136, Issue 8 https://doi.org/10.1021/ja4100035	journal	February 2014
Heme Enzyme Structure and Function Poulos, Thomas L. Chemical Reviews, Vol. 114, Issue 7 https://doi.org/10.1021/cr400415k	journal	January 2014
High-valent iron in chemical and biological oxidations Groves, John T. Journal of Inorganic Biochemistry, Vol. 100, Issue 4 https://doi.org/10.1016/j.jinorgbio.2006.01.012	journal	April 2006
Concerted electron-proton transfer in the optical excitation of hydrogen-bonded dyes Westlake, B. C.; Brennaman, M. K.; Concepcion, J. J. Proceedings of the National Academy of Sciences, Vol. 108, Issue 21 https://doi.org/10.1073/pnas.1104811108	journal	May 2011
Hydrogen Atom Abstraction by a High-Valent Manganese(V)−Oxo Corrolazine Lansky, David E.; Goldberg, David P. Inorganic Chemistry, Vol. 45, Issue 13 https://doi.org/10.1021/ic060491+	journal	May 2006
Two-State Reactivity, Electromerism, Tautomerism, and “Surprise” Isomers in the Formation of Compound II of the Enzyme Horseradish Peroxidase from the Principal Species, Compound I Derat, Etienne; Shaik, Sason Journal of the American Chemical Society, Vol. 128, Issue 25 https://doi.org/10.1021/ja0600734	journal	June 2006
Iron(IV)hydroxide pKa and the Role of Thiolate Ligation in C-H Bond Activation by Cytochrome P450 Yosca, T. H.; Rittle, J.; Krest, C. M. Science, Vol. 342, Issue 6160 https://doi.org/10.1126/science.1244373	journal	November 2013
Photoinduced Oxidation of Horseradish Peroxidase Berglund, Johan; Pascher, Torbjörn; Winkler, Jay R. Journal of the American Chemical Society, Vol. 119, Issue 10 https://doi.org/10.1021/ja961026m	journal	March 1997
Cytochrome P450: The Active Oxidant and Its Spectrum Rittle, Jonathan; Younker, Jarod M.; Green, Michael T. Inorganic Chemistry, Vol. 49, Issue 8 https://doi.org/10.1021/ic902062d	journal	April 2010
Substrate positioning controls the partition between halogenation and hydroxylation in the aliphatic halogenase, SyrB2 Matthews, M. L.; Neumann, C. S.; Miles, L. A. Proceedings of the National Academy of Sciences, Vol. 106, Issue 42 https://doi.org/10.1073/pnas.0909649106	journal	October 2009
Structure and Chemistry of Cytochrome P450 Denisov, Ilia G.; Makris, Thomas M.; Sligar, Stephen G. Chemical Reviews, Vol. 105, Issue 6 https://doi.org/10.1021/cr0307143	journal	June 2005
An ultra-stable oxoiron( iv ) complex and its blue conjugate base England, Jason; Bigelow, Jennifer O.; Van Heuvelen, Katherine M. Chem. Sci., Vol. 5, Issue 3 https://doi.org/10.1039/C3SC52755G	journal	January 2014
Role of metal–oxo complexes in the cleavage of C–H bonds Borovik, A. S. Chemical Society Reviews, Vol. 40, Issue 4 https://doi.org/10.1039/c0cs00165a	journal	January 2011
Substrate Placement Influences Reactivity in Non-heme Fe(II) Halogenases and Hydroxylases Kulik, Heather J.; Drennan, Catherine L. Journal of Biological Chemistry, Vol. 288, Issue 16 https://doi.org/10.1074/jbc.M112.415570	journal	February 2013
A tutorial for understanding chemical reactivity through the valence bond approach Usharani, Dandamudi; Lai, Wenzhen; Li, Chunsen Chem. Soc. Rev., Vol. 43, Issue 14 https://doi.org/10.1039/C4CS00043A	journal	January 2014
Oxygenase Activity in the Self-Hydroxylation of ( S )-2-Hydroxypropylphosphonic Acid Epoxidase Involved in Fosfomycin Biosynthesis Liu, Pinghua; Mehn, Mark P.; Yan, Feng Journal of the American Chemical Society, Vol. 126, Issue 33 https://doi.org/10.1021/ja0475050	journal	August 2004
Electron photodetachment from mercaptyl anions (RS-). Electron affinities of mercaptyl radicals and the sulfur-hydrogen bond strength in mercaptans Janousek, Bruce K.; Reed, Kenneth J.; Brauman, John I. Journal of the American Chemical Society, Vol. 102, Issue 9 https://doi.org/10.1021/ja00529a040	journal	April 1980
Hydrogen Atom Abstraction by Permanganate: Oxidations of Arylalkanes in Organic Solvents Gardner, Kimberly A.; Kuehnert, Linda L.; Mayer, James M. Inorganic Chemistry, Vol. 36, Issue 10 https://doi.org/10.1021/ic961297y	journal	May 1997
Fishing for peroxidase protons Groves, J. T.; Boaz, N. C. Science, Vol. 345, Issue 6193 https://doi.org/10.1126/science.1256754	journal	July 2014
Porphyrins. VII. The synthesis of porphyrins by the Rothemund reaction Badger, Gm; Jones, Ra; Laslett, Rl Australian Journal of Chemistry, Vol. 17, Issue 9 https://doi.org/10.1071/CH9641028	journal	January 1964
Catalytic oxidation of nitric oxide and nitrite mediated by water-soluble high-valent iron porphyrins at an ITO electrode Lei, Jianping; Ju, Huangxian; Ikeda, Osamu Journal of Electroanalytical Chemistry, Vol. 567, Issue 2 https://doi.org/10.1016/j.jelechem.2003.12.041	journal	June 2004
Crystallographic and Single-Crystal Spectral Analysis of the Peroxidase Ferryl Intermediate Meharenna, Yergalem T.; Doukov, Tzanko; Li, Huiying Biochemistry, Vol. 49, Issue 14 https://doi.org/10.1021/bi100238r	journal	April 2010
Kinetics of the oxidation of ferrocyanide by horseradish peroxidase compounds I and II Dunford, H. Brian; Hasinoff, Brian B. Biochemistry, Vol. 9, Issue 25 https://doi.org/10.1021/bi00827a015	journal	December 1970
Preparation and Characterization of a Dialkoxyiron(IV) Porphyrin Groves, John T.; Quinn, Robert; McMurry, Thomas J. Journal of the American Chemical Society, Vol. 107, Issue 2 https://doi.org/10.1021/ja00288a014	journal	January 1985
Oxidation of red ferryl [(FeIVO)2+] porphyrin complexes to green ferryl [(FeIVO)2+] porphyrin radical complexes Balch, Alan L.; Latos-Grazynski, Lechoslaw; Renner, Mark W. Journal of the American Chemical Society, Vol. 107, Issue 10 https://doi.org/10.1021/ja00296a031	journal	May 1985
Nature of the Ferryl Heme in Compounds I and II Gumiero, Andrea; Metcalfe, Clive L.; Pearson, Arwen R. Journal of Biological Chemistry, Vol. 286, Issue 2 https://doi.org/10.1074/jbc.M110.183483	journal	November 2010
Mechanistic Studies on Peroxide Activation by a Water-Soluble Iron(III)–Porphyrin: Implications for OO Bond Activation in Aqueous and Nonaqueous Solvents Wolak, Maria; van Eldik, Rudi Chemistry - A European Journal, Vol. 13, Issue 17 https://doi.org/10.1002/chem.200601148	journal	June 2007
Selective electrocatalysis of alkenes in aqueous media. A comparison of reactivities for oxoferryl porphyrin and oxoferryl porphyrin radical cation at room temperature Liu, Mao-Huang; Yeh, Chen-Yu; Su, Y. Oliver Chemical Communications, Issue 12 https://doi.org/10.1039/cc9960001437	journal	January 1996
Highly Selective Bromination of Tetramesitylporphyrin: An Easy Access to Robust Metalloporphyrins, M-Br8TMP and M-Br8TMPS. Examples of application in catalytic oxygenation and oxidation reactions. Hoffmann, Pascal; Labat, Gilles; Robert, Anne Tetrahedron Letters, Vol. 31, Issue 14 https://doi.org/10.1016/S0040-4039(00)88897-8	journal	January 1990
Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications Warren, Jeffrey J.; Tronic, Tristan A.; Mayer, James M. Chemical Reviews, Vol. 110, Issue 12 https://doi.org/10.1021/cr100085k	journal	December 2010
Rate Constants for Termination and TEMPO Trapping of Some Resonance Stabilized Hydroaromatic Radicals in the Liquid Phase Arends, I. W. C. E.; Mulder, P.; Clark, K. B. The Journal of Physical Chemistry, Vol. 99, Issue 20 https://doi.org/10.1021/j100020a047	journal	May 1995
Selective electrocatalysis of alkene oxidations in aqueous media. Electrochemical and spectral characterization of oxo-ferryl porphyrin, oxo-ferryl porphyrin radical cation and their reaction products with alkenes at room temperature Liu, Mao-huang; Su, Y. Oliver Journal of Electroanalytical Chemistry, Vol. 452, Issue 1 https://doi.org/10.1016/S0022-0728(98)00114-4	journal	July 1998
High-valent iron-porphyrin complexes related to peroxidase and cytochrome P-450 Groves, John T.; Haushalter, Robert C.; Nakamura, Mikio Journal of the American Chemical Society, Vol. 103, Issue 10 https://doi.org/10.1021/ja00400a075	journal	May 1981
Proton Delivery to Ferryl Heme in a Heme Peroxidase: Enzymatic Use of the Grotthuss Mechanism Efimov, Igor; Badyal, Sandip K.; Metcalfe, Clive L. Journal of the American Chemical Society, Vol. 133, Issue 39 https://doi.org/10.1021/ja2007017	journal	October 2011
Effect of the Axial Ligand on the Reactivity of the Oxoiron(IV) Porphyrin π-Cation Radical Complex: Higher Stabilization of the Product State Relative to the Reactant State Takahashi, Akihiro; Yamaki, Daisuke; Ikemura, Kenichiro Inorganic Chemistry, Vol. 51, Issue 13 https://doi.org/10.1021/ic3006597	journal	June 2012
Detection and Kinetic Characterization of a Highly Reactive Heme–Thiolate Peroxygenase Compound I Wang, Xiaoshi; Peter, Sebastian; Kinne, Matthias Journal of the American Chemical Society, Vol. 134, Issue 31 https://doi.org/10.1021/ja3049223	journal	July 2012
Resolution of concerted versus sequential mechanisms in photo-induced double-proton transfer reaction in 7-azaindole H-bonded dimer Catalan, J.; del Valle, J. C.; Kasha, M. Proceedings of the National Academy of Sciences, Vol. 96, Issue 15 https://doi.org/10.1073/pnas.96.15.8338	journal	July 1999
Hydrocarbon Hydroxylation by Cytochrome P450 Enzymes Ortiz de Montellano, Paul R. Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr9002193	journal	February 2010
Neutron cryo-crystallography captures the protonation state of ferryl heme in a peroxidase Casadei, C. M.; Gumiero, A.; Metcalfe, C. L. Science, Vol. 345, Issue 6193 https://doi.org/10.1126/science.1254398	journal	July 2014
Reaction of Horse Cytochrome c with the Radical and the Oxyferryl Heme in Cytochrome c Peroxidase Compound I Hahm, Seung; Miller, Mark A.; Geren, Lois Biochemistry, Vol. 33, Issue 6 https://doi.org/10.1021/bi00172a025	journal	February 1994
Photoinduced Oxidation of Microperoxidase-8: Generation of Ferryl and Cation-Radical Porphyrins Low, Donald W.; Winkler, Jay R.; Gray, Harry B. Journal of the American Chemical Society, Vol. 118, Issue 1 https://doi.org/10.1021/ja9530477	journal	January 1996
Crystal Structures and Functional Characterization of Wild-Type CYP101D1 and Its Active Site Mutants Batabyal, Dipanwita; Poulos, Thomas L. Biochemistry, Vol. 52, Issue 49 https://doi.org/10.1021/bi401330c	journal	November 2013
Proton Transfer Drives Protein Radical Formation in Helicobacter pylori Catalase but Not in Penicillium vitale Catalase Alfonso-Prieto, M.; Oberhofer, H.; Klein, M. L. Journal of the American Chemical Society, Vol. 133, Issue 12 https://doi.org/10.1021/ja1110706	journal	March 2011
Driving Force for Oxygen-Atom Transfer by Heme-Thiolate Enzymes Wang, Xiaoshi; Peter, Sebastian; Ullrich, René Angewandte Chemie International Edition, Vol. 52, Issue 35 https://doi.org/10.1002/anie.201302137	journal	July 2013
Water Promoting Electron Hole Transport between Tyrosine and Cysteine in Proteins via a Special Mechanism: Double Proton Coupled Electron Transfer Chen, Xiaohua; Ma, Guangcai; Sun, Weichao Journal of the American Chemical Society, Vol. 136, Issue 12 https://doi.org/10.1021/ja406340z	journal	March 2014
Sulfonated and acetamidosulfonylated tetraarylporphyrins as biomimetic oxidation catalysts under aqueous conditions Song, Rita; Robert, Anne; Bernadou, Jean Inorganica Chimica Acta, Vol. 272, Issue 1-2 https://doi.org/10.1016/S0020-1693(97)05944-6	journal	May 1998
Do spin state and spin density affect hydrogen atom transfer reactivity? Saouma, Caroline T.; Mayer, James M. Chem. Sci., Vol. 5, Issue 1 https://doi.org/10.1039/C3SC52664J	journal	January 2014
The concerted mechanism of photo-induced biprotonic transfer in 7-azaindole dimers: Structure, quantum-theoretical analysis, and simultaneity principles Catalan, J.; Perez, P.; del Valle, J. C. Proceedings of the National Academy of Sciences, Vol. 99, Issue 9 https://doi.org/10.1073/pnas.052703899	journal	April 2002
Using push to get pull Groves, John T. Nature Chemistry, Vol. 6, Issue 2 https://doi.org/10.1038/nchem.1855	journal	January 2014
Hydrogen Atom Abstraction by Metal−Oxo Complexes: Understanding the Analogy with Organic Radical Reactions Mayer, James M. Accounts of Chemical Research, Vol. 31, Issue 8 https://doi.org/10.1021/ar970171h	journal	August 1998
The reaction of 5,10,15,20-tetrakis(2,6-dichloro-3-sulfonatophenyl)porphinatoiron(III) hydrate with alkyl and acyl hydroperoxides. The dynamics of reaction of water-soluble and non .mu.-oxo dimer forming iron(III) porphyrins in aqueous solution. 7 Murata, Kazuhisa; Panicucci, Rick; Gopinath, Enona Journal of the American Chemical Society, Vol. 112, Issue 16 https://doi.org/10.1021/ja00172a025	journal	August 1990
Evidence that the Fosfomycin-Producing Epoxidase, HppE, Is a Non-Heme-Iron Peroxidase Wang, C.; Chang, W. -c.; Guo, Y. Science, Vol. 342, Issue 6161 https://doi.org/10.1126/science.1240373	journal	October 2013
Dramatically Accelerated Selective Oxygen-Atom Transfer by a Nonheme Iron(IV)-Oxo Complex: Tuning of the First and Second Coordination Spheres Widger, Leland R.; Davies, Casey G.; Yang, Tzuhsiung Journal of the American Chemical Society, Vol. 136, Issue 7 https://doi.org/10.1021/ja410240c	journal	February 2014
Redox Potentials of Oxoiron(IV) Porphyrin π-Cation Radical Complexes: Participation of Electron Transfer Process in Oxygenation Reactions Takahashi, Akihiro; Kurahashi, Takuya; Fujii, Hiroshi Inorganic Chemistry, Vol. 50, Issue 15 https://doi.org/10.1021/ic102564e	journal	August 2011
On the Catalytic Mechanism of ( S )-2-Hydroxypropylphosphonic Acid Epoxidase (HppE): A Hybrid DFT Study Miłaczewska, Anna; Broclawik, Ewa; Borowski, Tomasz Chemistry - A European Journal, Vol. 19, Issue 2 https://doi.org/10.1002/chem.201202825	journal	November 2012
Electronic structure and reactivity of high-valent oxo iron porphyrins Fujii, Hiroshi Coordination Chemistry Reviews, Vol. 226, Issue 1-2 https://doi.org/10.1016/S0010-8545(01)00441-6	journal	March 2002
Elucidation of the Fe(iv)=O intermediate in the catalytic cycle of the halogenase SyrB2 Wong, Shaun D.; Srnec, Martin; Matthews, Megan L. Nature, Vol. 499, Issue 7458 https://doi.org/10.1038/nature12304	journal	July 2013
Electron-transfer properties of high-valent metal-oxo complexes Fukuzumi, Shunichi Coordination Chemistry Reviews, Vol. 257, Issue 9-10 https://doi.org/10.1016/j.ccr.2012.07.021	journal	May 2013
The Role of Chloride in the Mechanism of O ₂ Activation at the Mononuclear Nonheme Fe(II) Center of the Halogenase HctB Pratter, Sarah M.; Light, Kenneth M.; Solomon, Edward I. Journal of the American Chemical Society, Vol. 136, Issue 26 https://doi.org/10.1021/ja503179m	journal	June 2014
Dynamics of the reaction of hydrogen peroxide with a water soluble non .mu.-oxo dimer forming iron(III) tetraphenylporphyrin. 2. The reaction of hydrogen peroxide with 5,10,15,20-tetrakis(2,6-dichloro-3-sulfonatophenyl)porphinato iron(III) in aqueous solution Panicucci, Rick; Bruice, Thomas C. Journal of the American Chemical Society, Vol. 112, Issue 16 https://doi.org/10.1021/ja00172a024	journal	August 1990
Resonance Raman and magnetic resonance spectroscopic characterization of the Fe(I), Fe(II), Fe(III), and Fe(IV) oxidation states of Fe(2-TMPyP)n+(aq) Rodgers, Kenton R.; Reed, Robert A.; Su, Y. Oliver Inorganic Chemistry, Vol. 31, Issue 13 https://doi.org/10.1021/ic00039a007	journal	June 1992
Dichotomous Hydrogen Atom Transfer vs Proton-Coupled Electron Transfer During Activation of X–H Bonds (X = C, N, O) by Nonheme Iron–Oxo Complexes of Variable Basicity Usharani, Dandamudi; Lacy, David C.; Borovik, A. S. Journal of the American Chemical Society, Vol. 135, Issue 45 https://doi.org/10.1021/ja408073m	journal	October 2013
New Procedures for the Synthesis and Analysis of 5,10,15,20-Tetrakis(sulphophenyl)porphyrins and Derivatives through Chlorosulphonation A. W. Johnstone, Robert; M. d'A. Rocha Gonsalves, Antonio; M. Pereira, Mariette HETEROCYCLES, Vol. 43, Issue 4 https://doi.org/10.3987/COM-95-7372	journal	January 1996
Cytochrome P450 Compound I: Capture, Characterization, and C-H Bond Activation Kinetics Rittle, J.; Green, M. T. Science, Vol. 330, Issue 6006 https://doi.org/10.1126/science.1193478	journal	November 2010
Oxoiron(IV) in Chloroperoxidase Compound II Is Basic: Implications for P450 Chemistry Green, M. T. Science, Vol. 304, Issue 5677 https://doi.org/10.1126/science.1096897	journal	June 2004
δ Conversion Parameter between pH Scales ( and ) in Acetonitrile/Water Mixtures at Various Compositions and Temperatures Gagliardi, Leonardo G.; Castells, Cecilia B.; Ràfols, Clara Analytical Chemistry, Vol. 79, Issue 8 https://doi.org/10.1021/ac062372h	journal	April 2007
Electrostatic Environment of Hemes in Proteins: p K _a s of Hydroxyl Ligands ^† Song, Yifan; Mao, Junjun; Gunner, M. R. Biochemistry, Vol. 45, Issue 26 https://doi.org/10.1021/bi052182l	journal	July 2006
The spectra of the enzyme-substrate complexes of catalase and peroxidase Chance, Britton Archives of Biochemistry and Biophysics, Vol. 41, Issue 2 https://doi.org/10.1016/0003-9861(52)90469-4	journal	December 1952
P450 Enzymes: Their Structure, Reactivity, and Selectivity—Modeled by QM/MM Calculations Shaik, Sason; Cohen, Shimrit; Wang, Yong Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr900121s	journal	February 2010
The one-electron reduction potential of 4-substituted phenoxyl radicals in water Lind, J.; Shen, X.; Eriksen, T. E. Journal of the American Chemical Society, Vol. 112, Issue 2 https://doi.org/10.1021/ja00158a002	journal	January 1990
Equilibrium acidities in dimethyl sulfoxide solution Bordwell, Frederick G. Accounts of Chemical Research, Vol. 21, Issue 12 https://doi.org/10.1021/ar00156a004	journal	December 1988
Equilibrium between Fe(iv) porphyrin and Fe(iii) porphyrin radical cation: new insight into the electronic structure of high-valent iron porphyrin complexes Ikezaki, Akira; Takahashi, Masashi; Nakamura, Mikio Chemical Communications, Vol. 49, Issue 30 https://doi.org/10.1039/c3cc40319j	journal	January 2013
The chemical nature of the second hydrogen peroxide compound formed by cytochrome c peroxidase and horseradish peroxidase. 1. Titration with reducing agents George, P. Biochemical Journal, Vol. 54, Issue 2 https://doi.org/10.1042/bj0540267	journal	May 1953
Oxidations catalyzed by fungal peroxygenases Hofrichter, Martin; Ullrich, René Current Opinion in Chemical Biology, Vol. 19 https://doi.org/10.1016/j.cbpa.2014.01.015	journal	April 2014
Catalytic mechanism of cytochrome P-450: evidence for a distal charge relay Gerber, Nancy C.; Sligar, Stephen G. Journal of the American Chemical Society, Vol. 114, Issue 22 https://doi.org/10.1021/ja00048a081	journal	October 1992
Studies on Cytochrome c Peroxidase Coulson, Andrew F. W.; Erman, James E.; Yonetani, Takashi Journal of Biological Chemistry, Vol. 246, Issue 4 https://doi.org/10.1016/S0021-9258(18)62411-1	journal	February 1971

Cited By (10)

Direct visualization of a Fe(IV)–OH intermediate in a heme enzyme Kwon, Hanna; Basran, Jaswir; Casadei, Cecilia M. Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms13445	journal	November 2016
Heme-thiolate ferryl of aromatic peroxygenase is basic and reactive Wang, Xiaoshi; Ullrich, René; Hofrichter, Martin Proceedings of the National Academy of Sciences https://doi.org/10.1073/pnas.1503340112	journal	March 2015
Accelerated Oxygen Atom Transfer and C−H Bond Oxygenation by Remote Redox Changes in Fe ₃ Mn-Iodosobenzene Adducts de Ruiter, Graham; Carsch, Kurtis M.; Gul, Sheraz Angewandte Chemie, Vol. 129, Issue 17 https://doi.org/10.1002/ange.201701319	journal	March 2017
Oxidation Reactions with Bioinspired Mononuclear Non-Heme Metal-Oxo Complexes Engelmann, Xenia; Monte-Pérez, Inés; Ray, Kallol Angewandte Chemie International Edition, Vol. 55, Issue 27 https://doi.org/10.1002/anie.201600507	journal	June 2016
High-valent iron (Fe ^VI , Fe ^V , and Fe ^IV ) species in water: characterization and oxidative transformation of estrogenic hormones Machalová Šišková, Karolína; Jančula, Daniel; Drahoš, Bohuslav Physical Chemistry Chemical Physics, Vol. 18, Issue 28 https://doi.org/10.1039/c6cp02216b	journal	January 2016
Accelerated Oxygen Atom Transfer and C−H Bond Oxygenation by Remote Redox Changes in Fe ₃ Mn-Iodosobenzene Adducts de Ruiter, Graham; Carsch, Kurtis M.; Gul, Sheraz Angewandte Chemie International Edition, Vol. 56, Issue 17 https://doi.org/10.1002/anie.201701319	journal	March 2017
Lewis Acid Coupled Electron Transfer of Metal-Oxygen Intermediates Fukuzumi, Shunichi; Ohkubo, Kei; Lee, Yong-Min Chemistry - A European Journal, Vol. 21, Issue 49 https://doi.org/10.1002/chem.201502693	journal	September 2015
Oxidationsreaktionen mit bioinspirierten einkernigen Nicht-Häm-Oxidometallkomplexen Engelmann, Xenia; Monte-Pérez, Inés; Ray, Kallol Angewandte Chemie, Vol. 128, Issue 27 https://doi.org/10.1002/ange.201600507	journal	June 2016
Beyond ferryl-mediated hydroxylation: 40 years of the rebound mechanism and C–H activation Huang, Xiongyi; Groves, John T. JBIC Journal of Biological Inorganic Chemistry, Vol. 22, Issue 2-3 https://doi.org/10.1007/s00775-016-1414-3	journal	December 2016
Function Coupling Mechanism of PhuS and HemO in Heme Degradation Lee, Michael J. Y.; Wang, Ye; Jiang, Yafei Scientific Reports, Vol. 7, Issue 1 https://doi.org/10.1038/s41598-017-11907-5	journal	September 2017

Similar Records

Ferryl Protonation in Oxoiron(IV) Porphyrins and Its Role in Oxygen Transfer

Journal Article · Wed Feb 04 00:00:00 EST 2015 · Journal of the American Chemical Society · OSTI ID:1385431

Boaz, Nicholas C.; Bell, Seth R.; Groves, John T.

Aqueous Ferryl(IV) Ion: Kinetics of Oxygen Atom Transfer to Substrates and Oxo Exchange with Solvent Water

Journal Article · Tue Nov 01 00:00:00 EST 2005 · Inorganic Chemistry · OSTI ID:1385431

Pestovsky, Oleg; Bakac, Andreja

REVERSIBLE FORMATION OF IODOSYLBENZENE-IRON PORPHYRIN INTERMEDIATES IN THE REACTION OF OXOIRON(IV) PORPHYRIN PI-CATION RADICALS AND IODOBENZENE

Journal Article · Wed Jan 01 00:00:00 EST 2003 · Angewandte Chemie. International Edition in English · OSTI ID:1385431

NAM, W; CHOI, S; LIM, M; +4 more

Related Subjects

catalysis (homogeneous)
catalysis (heterogeneous)
bio-inspired
hydrogen and fuel cells
materials and chemistry by design
synthesis (novel materials)

Title: Ferryl Protonation in Oxoiron(IV) Porphyrins and Its Role in Oxygen Transfer

Citation Formats

References (85)

Cited By (10)

Similar Records

Related Subjects