The Experimentally Elusive Oxidant of Cytochrome P450: A Theoretical "Trapping" Defining More Closely the "Real" Species

Just like a chameleon changes color, a model of cytochrome P450 compound I (1) adapts its electronic and geometric features to the protein environment which accommodates it. The electronic ground state of 1 is assigned by quantum chemical calculations as an antiferromagnetic 2A2u state.

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Published inChembiochem : a European journal of chemical biology Vol. 2; no. 11; pp. 848 - 851
Main Authors Ogliaro, François, de Visser, Samuël P., Cohen, Shimrit, Kaneti, Jose, Shaik, Sason
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 05.11.2001
WILEY‐VCH Verlag GmbH
Subjects
Cytochrome P-450 Enzyme System - chemistry
cytochromes
density functional calculations
Electron Spin Resonance Spectroscopy
hydrogen bonds
Models, Molecular
Oxidants - chemistry
Oxidation-Reduction
porphyrins
Protein Conformation
solvent effects
Spin Trapping
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Abstract Just like a chameleon changes color, a model of cytochrome P450 compound I (1) adapts its electronic and geometric features to the protein environment which accommodates it. The electronic ground state of 1 is assigned by quantum chemical calculations as an antiferromagnetic 2A2u state.
AbstractList Just like a chameleon changes color, a model of cytochrome P450 compound I (1) adapts its electronic and geometric features to the protein environment which accommodates it. The electronic ground state of 1 is assigned by quantum chemical calculations as an antiferromagnetic 2A2u state.
Author de Visser, Samuël P.
Shaik, Sason
Ogliaro, François
Cohen, Shimrit
Kaneti, Jose
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  organization: Department of Organic Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry The Hebrew University Givat Ram Campus, 91904 Jerusalem (Israel) Fax: (+972) 2-6584680
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References F. Ogliaro , S. Cohen , M. Filatov , N. Harris , S. Shaik , Angew. Chem. 2000, 112, 4009
F. Ogliaro , S. P. de Visser , J. T. Groves , S. Shaik , Angew. Chem. 2001, 113, 2958
Angew. Chem. Int. Ed. 2000, 39, 3851.
I. Schlichting , J. Berendzen , K. Chu , A. M. Stock , S. A. Maves , D. E. Benson , B. M. Sweet , D. Ringe , G. A. Petsko , S. G. Sligar , Science 2000, 287, 615.
J. T. Groves , Y.-Z. Hang in Cytochrome P450: Structure, Mechanisms and Biochemistry, 2nd ed. (Ed.: P. R. Ortiz de Montellano), Plenum, New York, 1995, pp. 3-48.
C. M. Hosten , A. M. Sullivan , V. Palaniappan , M. M. Fitzgerald , J. Terner , J. Biol. Chem. 1994, 269, 13 966.
N. Suzuki , T. Higuchi , Y. Urano , K. Kikuchi , H. Uekusa , Y. Ohashi , T. Uchida , T. Kitagawa , T. Nagano , J. Am. Chem. Soc. 1999, 121, 11 571.
B. Marten , K. Kim , C. Cortis , R. A. Friesner , R. B. Murphy , M. N. Ringnalda , D. Sitkoff , B. Honig , J. Phys. Chem. 1995, 99, 16 479.
T. Egawa , H. Shimada , Y. Ishimura , Biophys. Biochem. Res. Commun. 1994, 201, 1464.
D. Harris , G. Loew , L. Waskell , J. Inorg. Biochem. 2001, 83, 309.
R. Davydov , T. M. Makris , V. Kofman , D. E. Werst , S. G. Sligar , B. M. Hoffman , J. Am. Chem. Soc. 2001, 123, 1403.
J. A. Sigman , A. E. Pond , J. H. Dawson , Y. Lu , Biochemistry 1999, 38, 11 122.
For a summary, see: G. H. Loew , D. L. Harris , Chem. Rev. 2000, 100, 407
F. Ogliaro , S. Cohen , S. Shaik , J. Am. Chem. Soc. 2000, 122, 12 892.
Angew. Chem. Int. Ed. 2001, 40, 2874.
R. Weiss , D. Mandon , T. Wolter , A. X. Trautwein , M. Muther , E. Bill , A. Gold , K. Jayaraj , J. Terner , J. Bioinorg. Chem. 1996, 1, 377.
J. H. Dawson , Science 1988, 240, 433.
R. Rutter , M. Valentine , M. P. Hendrich , L. P. Hager , P. G. Debrunner , Biochemistry 1983, 22, 9769.
1994; 201
2001; 123
2001; 83
1994; 269
2001 2001; 113 40
1999; 38
1995; 99
1999; 121
1995
1996; 1
2000; 287
2000; 100
2000; 122
1988; 240
2000 2000; 112 39
1983; 22
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  start-page: 407
  year: 2000
  publication-title: Chem. Rev.
– volume: 123
  start-page: 1403
  year: 2001
  publication-title: J. Am. Chem. Soc.
– volume: 287
  start-page: 615
  year: 2000
  publication-title: Science
– volume: 269
  start-page: 13 966
  year: 1994
  publication-title: J. Biol. Chem.
– volume: 112 39
  start-page: 4009 3851
  year: 2000 2000
  publication-title: Angew. Chem. Angew. Chem. Int. Ed.
– volume: 240
  start-page: 433
  year: 1988
  publication-title: Science
– volume: 99
  start-page: 16 479
  year: 1995
  publication-title: J. Phys. Chem.
– volume: 1
  start-page: 377
  year: 1996
  publication-title: J. Bioinorg. Chem.
– volume: 121
  start-page: 11 571
  year: 1999
  publication-title: J. Am. Chem. Soc.
– year: 1995
– start-page: 3
  year: 1995
  end-page: 48
– volume: 122
  start-page: 12 892
  year: 2000
  publication-title: J. Am. Chem. Soc.
– volume: 83
  start-page: 309
  year: 2001
  publication-title: J. Inorg. Biochem.
– volume: 113 40
  start-page: 2958 2874
  year: 2001 2001
  publication-title: Angew. Chem. Angew. Chem. Int. Ed.
– volume: 22
  start-page: 9769
  year: 1983
  publication-title: Biochemistry
– volume: 201
  start-page: 1464
  year: 1994
  publication-title: Biophys. Biochem. Res. Commun.
– volume: 38
  start-page: 11 122
  year: 1999
  publication-title: Biochemistry
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Snippet Just like a chameleon changes color, a model of cytochrome P450 compound I (1) adapts its electronic and geometric features to the protein environment which...
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SubjectTerms Cytochrome P-450 Enzyme System - chemistry
cytochromes
density functional calculations
Electron Spin Resonance Spectroscopy
hydrogen bonds
Models, Molecular
Oxidants - chemistry
Oxidation-Reduction
porphyrins
Protein Conformation
solvent effects
Spin Trapping
Title The Experimentally Elusive Oxidant of Cytochrome P450: A Theoretical "Trapping" Defining More Closely the "Real" Species
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https://www.ncbi.nlm.nih.gov/pubmed/11948872
Volume 2
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