Direct Comparison of the reactivity of model complexes for compounds 0, I, and II in oxygenation, hydrogen-abstraction, and hydride-transfer processes

Chemistry - A European Journal

Volumn 15, Issue 48, 2009, Pages 13435-13440

  Fertinger, Christoph ^a   Hessenaue Ilicheva, Natalya ^a   Franke, Alicja ^a   Van Eldik, Rudi ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Enzyme models; Iron; Kinetics; Reaction mechanisms; Reactivity

Indexed keywords

CATALYTIC REACTIONS; CHEMICAL NATURE; CYTOCHROME P450; ENZYME MODELS; HYDRIDE TRANSFERS; HYDROGEN ABSTRACTION; KINETIC MEASUREMENT; LOW TEMPERATURES; MESO-TETRAMESITYLPORPHYRIN; MODEL COMPLEXES; REACTION CONDITIONS; REACTION MECHANISM; REACTIVE INTERMEDIATE; TRANSFER PROCESS; UV/ VIS SPECTROSCOPY; VARIOUS SUBSTRATES;

ABSTRACTING; BIOLOGICAL SYSTEMS; BIOMIMETICS; CATALYSIS; ENZYMES; IRON COMPOUNDS; OXYGENATION; OXYGENATORS; RATE CONSTANTS;

CHEMICAL REACTIVITY;

CYTOCHROME P450; HYDROGEN; IRON; IRON(III) MESO TETRAMESITYLPORPHYRIN; IRON(III) MESO-TETRAMESITYLPORPHYRIN; METALLOPORPHYRIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY; KINETICS; OXIDATION REDUCTION REACTION;

CYTOCHROME P-450 ENZYME SYSTEM; HYDROGEN; IRON; KINETICS; METALLOPORPHYRINS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SUBSTRATE SPECIFICITY;

EID: 72449205479     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901804     Document Type: Article

References (40)

1. a) I. G. Denisov, T. M. Makris, S. G. Sugar, I. Schlichting, Chem. Rev. 2005, 105, 2253;
2. b) D. Mansuy, C. R. Chim. 2007, 10, 392;
3. c) B. Meunier, S. P. de Visser, S. Shaik, Chem. Rev. 2004, 104, 3947;
4. d) W. Nam, Acc. Chem. Res. 2007, 40, 522;
5. e) P. R. Ortiz de Montellano, Cytochrome P450: Structure, Mechanism, and Biochemistry, 3rd ed. (Ed.: P. R. Ortiz de Montellano), Kluwer Academic/Plenum Publishers, New York, 2005.
6. a) W. Nam, Y. O. Ryu, W. J. Song, J. Biol. Inorg. Chem. 2004, 9, 654;
7. b) W. Nam, M. H. Lim, H. J. Lee, C. Kim, J. Am. Chem. Soc. 2000, 122, 6641;
8. c) J. P. Coliman, A. S. Chien, T. A. Eberspacher, J. I. Brauman, J. Am. Chem. Soc. 2000, 122, 11098;
9. d) J. P. Collman, L. Zeng, R. A. Decréau, Chem. Commun. 2003, 2974;
10. e) K. Machii, Y. Watanabe, I. Morishima, J. Am. Chem. Soc. 1995, 117, 6691;
11. f) W. Nam, S. W. Jin, M. H. Lim, J.Y. Ryu, C. Kim, Inorg. Chem. 2002, 41, 3647;
12. g) S. Jin, T. A. Bryson, J. H. Dawson, J. Biol. Inorg. Chem. 2004, 9, 644;
13. h) A. D. N. Vaz, D. F. McGinnity, M. J. Coon, Proc. Natl. Acad. Sci, USA 1998, 95, 3555;
14. i) A. D. N. Vaz, S. J. Pernecky, G. M. Raner, M. J. Coon, Proc. Natl. Acad. Sci. USA 1996, 93, 4644;
15. j) F. Ogliaro, S. P. de Visser, S. Cohen, P. K. Sharma, S. Shaik, J. Am. Chem. Soc. 2002, 124, 2806;
16. k) M. Eda, T. Kamachi, K. Yoshizawa, T. Toraya, Bull. Chem. Soc. Jpn. 2002, 75, 1469;
17. l) S. Shaik, D. Kumar, S. P. de Visser, A. Altun, W. Thiel, Chem. Rev. 2005, 105, 2279;
18. m) S. Shaik, H. Hirao, D. Kumar, Acc. Chem. Res. 2007, 40, 532;
19. n) M. J. Cryle, J. J. De Voss, Angew. Chem. 2006, 118, 8401;
20. Angew. Chem. Int. Ed. 2006, 45, 8221;
21. o) P. R. Ortiz de Montellano, J. J. De Voss, Nat. Prod. Rep. 2002, 19, 477;
22. p) C. Li, L. Zhang, C. Zhang, H. Hirao, W. Wu, S. Shaik, Angew. Chem. 2007, 119, 8316.
23. A. Franke, C. Fertinger, R. van Eldik, Angew. Chem. 2008, 120, 5316;
24. Angew. Chem. Int. Ed. 2008, 47, 5238.
25. a) J.T. Groves, Y. Watanabe, J. Am. Chem. Soc. 1986, 108, 7834;
26. b) J. T. Groves, Y. Watanabe, J. Am. Chem. Soc. 1988, 110, 8443.
27. M. Wolak, R. van Eldik, Chem. Eur. J. 2007, 13, 4873.
28. W. J. Song, Y. J. Sun, S. K. Choi, W. Nam, Chem. Eur. J. 2006, 12, 130.
29. Z. Pan, M. Newcomb, Inorg. Chem. 2007, 46, 6767.
30. a) M. J. Park, J. Lee, Y. Suh, J. Kim, W. Nam, J. Am. Chem. Soc. 2006, 128, 2630;
31. b) M. S. Seo, T. Kamachi, T. Kouno, K. Murata, M. J. Park, K. Yoshizawa, W. Nam, Angew. Chem. 2007, 119, 2341;
32. Angew. Chem. Int. Ed. 2007, 46, 2291.
33. S. E. Stein, R. L. Brown, J. Am. Chem. Soc. 1991, 113, 787.
34. Y. J. Jeong, Y. Kang, A.-R. Han, Y.-M. Lee, H. Kotani, S. Fukuzumi, W. Nam, Angew. Chem. 2008, 120, 7431;
35. Angew. Chem. Int. Ed. 2008, 47, 1321.
36. X.-Q. Zhu, H.-R. Li, Q. Li, T. Ai, J.-Y. Lu, Y. Yang, J.-P. Cheng, Chem. Eur. J. 2003, 9, 871.
37. N. Hessenauer-Ilicheva, A. Franke, D. Meyer, W.-D. Woggon, R. van Eldik, J. Am. Chem. Soc. 2007, 129, 12473.
38. R.-J. Cheng, L. Latos-Grazynski, A. L. Balch, Inorg. Chem. 1982, 21, 2412.
39. H. Saltzmann, J. G. Sharefkin, Org. Synth. 1963, 43, 60.
40. R. M. G. Roberts, D. Ostović, M. M. Kreevoy, Faraday Discuss. Chem. Soc. 1982, 74, 257.