Literature DB >> 16774243

Kinetics of two-electron oxidations by the compound I derivative of chloroperoxidase, a model for cytochrome P450 oxidants.

Rui Zhang1, Nandini Nagraj, Dharmika S P Lansakara-P, Lowell P Hager, Martin Newcomb.   

Abstract

[structure: see text] Rate constants for two-electron oxidation reactions of Compound I from chloroperoxidase (CPO) with a variety of substrates were measured by stopped-flow kinetic techniques. The thiolate ligand of CPO Compound I activates the iron-oxo species with the result that oxidation reactions are 2 to 3 orders of magnitude faster than oxidations by model iron(IV)-oxo porphyrin radical cations containing weaker binding counterions.

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Year:  2006        PMID： 16774243      PMCID： PMC2535770          DOI： 10.1021/ol060762k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  28 in total

1.  Heme-Containing Oxygenases.

Authors:  Masanori Sono; Mark P. Roach; Eric D. Coulter; John H. Dawson
Journal:  Chem Rev       Date:  1996-11-07       Impact factor: 60.622

Review 2.  Structure and chemistry of cytochrome P450.

Authors:  Ilia G Denisov; Thomas M Makris; Stephen G Sligar; Ilme Schlichting
Journal:  Chem Rev       Date:  2005-06       Impact factor: 60.622

3.  The crystal structure of chloroperoxidase: a heme peroxidase--cytochrome P450 functional hybrid.

Authors:  M Sundaramoorthy; J Terner; T L Poulos
Journal:  Structure       Date:  1995-12-15       Impact factor: 5.006

4.  Identification of intermediates in the catalytic cycle of chloroperoxidase.

Authors:  H A Wagenknecht; W D Woggon
Journal:  Chem Biol       Date:  1997-05

5.  Effects of a thiolate axial ligand on the pi-->pi* electronic states of oxoferryl porphyrins: a study of the optical and resonance Raman spectra of compounds I and II of chloroperoxidase.

Authors:  T Egawa; D A Proshlyakov; H Miki; R Makino; T Ogura; T Kitagawa; Y Ishimura
Journal:  J Biol Inorg Chem       Date:  2001-01       Impact factor: 3.358

6.  Chloroperoxidase. I. Isolation and properties of the crystalline glycoprotein.

Authors:  D R Morris; L P Hager
Journal:  J Biol Chem       Date:  1966-04-25       Impact factor: 5.157

7.  Hydroxylation of camphor by reduced oxy-cytochrome P450cam: mechanistic implications of EPR and ENDOR studies of catalytic intermediates in native and mutant enzymes.

Authors:  R Davydov; T M Makris; V Kofman; D E Werst; S G Sligar; B M Hoffman
Journal:  J Am Chem Soc       Date:  2001-02-21       Impact factor: 15.419

8.  Multiple active intermediates in oxidation reaction catalyzed by synthetic heme-thiolate complex relevant to cytochrome p450.

Authors:  Noriyuki Suzuki; Tsunehiko Higuchi; Tetsuo Nagano
Journal:  J Am Chem Soc       Date:  2002-08-14       Impact factor: 15.419

9.  Kinetic analysis of compound I formation and the catalatic activity of chloroperoxidase.

Authors:  T Araiso; R Rutter; M M Palcic; L P Hager; H B Dunford
Journal:  Can J Biochem       Date:  1981-04

10.  Reaction of myeloperoxidase compound I with chloride, bromide, iodide, and thiocyanate.

Authors:  P G Furtmüller; U Burner; C Obinger
Journal:  Biochemistry       Date:  1998-12-22       Impact factor: 3.162
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  17 in total

1.  Probing the oxyferrous and catalytically active ferryl states of Amphitrite ornata dehaloperoxidase by cryoreduction and EPR/ENDOR spectroscopy. Detection of compound I.

Authors:  Roman Davydov; Robert L Osborne; Muralidharan Shanmugam; Jing Du; John H Dawson; Brian M Hoffman
Journal:  J Am Chem Soc       Date:  2010-10-27       Impact factor: 15.419

2.  Low temperature photo-oxidation of chloroperoxidase Compound II.

Authors:  Xinting Yuan; Xin Sheng; John H Horner; Brian Bennett; Leslie W-M Fung; Martin Newcomb
Journal:  J Inorg Biochem       Date:  2010-07-17       Impact factor: 4.155

3.  Epoxidation Catalyzed by the Nonheme Iron(II)- and 2-Oxoglutarate-Dependent Oxygenase, AsqJ: Mechanistic Elucidation of Oxygen Atom Transfer by a Ferryl Intermediate.

Authors:  Jikun Li; Hsuan-Jen Liao; Yijie Tang; Jhih-Liang Huang; Lide Cha; Te-Sheng Lin; Justin L Lee; Igor V Kurnikov; Maria G Kurnikova; Wei-Chen Chang; Nei-Li Chan; Yisong Guo
Journal:  J Am Chem Soc       Date:  2020-03-16       Impact factor: 15.419

4.  Detection and kinetic characterization of a highly reactive heme-thiolate peroxygenase compound I.

Authors:  Xiaoshi Wang; Sebastian Peter; Matthias Kinne; Martin Hofrichter; John T Groves
Journal:  J Am Chem Soc       Date:  2012-07-26       Impact factor: 15.419

5.  Spectra and kinetic studies of the compound I derivative of cytochrome P450 119.

Authors:  Xin Sheng; John H Horner; Martin Newcomb
Journal:  J Am Chem Soc       Date:  2008-09-13       Impact factor: 15.419

6.  Photochemical production of a highly reactive porphyrin-iron-oxo species.

Authors:  Zhengzheng Pan; Rui Zhang; Leslie W-M Fung; Martin Newcomb
Journal:  Inorg Chem       Date:  2007-02-07       Impact factor: 5.165

Review 7.  Laser flash photolysis generation of high-valent transition metal-oxo species: insights from kinetic studies in real time.

Authors:  Rui Zhang; Martin Newcomb
Journal:  Acc Chem Res       Date:  2008-02-16       Impact factor: 22.384

8.  Kinetics and activation parameters for oxidations of styrene by Compounds I from the cytochrome P450(BM-3) (CYP102A1) heme domain and from CYP119.

Authors:  Xinting Yuan; Qin Wang; John H Horner; Xin Sheng; Martin Newcomb
Journal:  Biochemistry       Date:  2009-09-29       Impact factor: 3.162

9.  Quantitative production of compound I from a cytochrome P450 enzyme at low temperatures. Kinetics, activation parameters, and kinetic isotope effects for oxidation of benzyl alcohol.

Authors:  Qin Wang; Xin Sheng; John H Horner; Martin Newcomb
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

10.  Explaining the atypical reaction profiles of heme enzymes with a novel mechanistic hypothesis and kinetic treatment.

Authors:  Kelath Murali Manoj; Arun Baburaj; Binoy Ephraim; Febin Pappachan; Pravitha Parapurathu Maviliparambathu; Umesh K Vijayan; Sivaprasad Valiyaveettil Narayanan; Kalaiselvi Periasamy; Ebi Ashley George; Lazar T Mathew
Journal:  PLoS One       Date:  2010-05-17       Impact factor: 3.240
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