The "Rebound Controversy": An Overview and Theoretical Modeling of the Rebound Step in C-H Hydroxylation by Cytochrome P450

European Journal of Inorganic Chemistry

Volumn , Issue 2, 2004, Pages 207-226

  Shaik, Sason ^a   Cohen, Shimrit ^a   De Visser, Samuël P ^a   Sharma, Pankaz K ^a   Kumar, Devesh ^a   Kozuch, Sebastian ^a   Ogliaro, François ^a   Danovich, David ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Alkanes; C H hydroxylation; Cytochrome P450; Density functional calculations; Enzyme catalysis; Free radicals

Indexed keywords

ENZYMES; FORECASTING; FREE RADICALS; HYDROXYLATION; PARAFFINS;

ALKYL RADICALS; C-H HYDROXYLATION; CYTOCHROMES P450; DENSITY-FUNCTIONAL CALCULATIONS; ENZYME CATALYSIS; HIGH SPINS; HYDROGEN ABSTRACTION; SPIN SURFACES; THEORETICAL MODELING; TWO-STATE REACTIVITY;

DENSITY FUNCTIONAL THEORY;

ALCOHOL DERIVATIVE; ALKANE; ALKYL GROUP; CYTOCHROME P450; FERRIC ION; IRON DERIVATIVE; RADICAL;

COMPLEX FORMATION; ENZYME SUBSTRATE; HYDROXYLATION; REACTION ANALYSIS; SHORT SURVEY; SURFACE PROPERTY; THEORETICAL MODEL;

EID: 0742288622     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200300448     Document Type: Short Survey

References (79)

1. Cytochrome P450: Structure. Mechanisms and Biochemistry (Ed.: P. R. Ortiz de Montellano), 2nd ed., Plenum Press, New York, 1995.
2. J. T. Groves, G. A. McClusky, J. Am. Chem. Soc. 1976, 98, 859-861.
3. P. R. Ortiz de Montellano, J. J. De Voss, Natl. Prod. Rep. 2002, 19, 1-18.
4. J. T. Groves, G. A. McClusky, R. E. White, M. J. Coon, Biochem. Biophys. Res. Commun. 1978, 81, 154-160.
5. A. Sorokin, A. Robert, B. Meunier, J. Am. Chem. Soc. 1993, 115, 7293-7299.
6. M. H. Gelb, D. C. Heimbrook, P. Mälkönen, S. G. Sligar, Biochemistry 1982, 21, 370-377.
7. M. Sono, M. P. Roach, E. D. Coulter, J. H. Dawson, Chem. Rev. 1996, 96, 2841-2888.
8. W.-D. Woggon, Top. Curr. Chem. 1996, 184, 39-95.
9. J. T. Groves, Y.-Z. Han, in Cytochrome P450: Structure, Mechanism and Biochemistry (Ed.: P. R. Ortiz de Montellano) 2nd ed., Plenum Press, New York, 1995, pp. 3-48.
10. B. Meunier, J. Bernadou, Top. Catal. 2002, 21, 47-55.
11. H. Fretz, W.-D. Woggon, R. Voges, Helv. Chim. Acta 1989, 72, 391-400.
12. P. R. Ortiz de Montellano, R. A. Stearns, J. Am. Chem. Soc. 1987, 109, 3415-3420.
13. C. Audergon, K. R. Iyer, J. P. Jones, J. F. Darbyshire, W. F. Trager, J. Am. Chem. Soc. 1999, 121, 41-47.
14. H. Lee, P. R. Ortiz de Montellano, A. E. McDermott, Biochemistry 1999, 38, 10808-10813.
15. M. Newcomb, P. H. Toy, Acc. Chem. Res. 2000, 33, 449-455.
16. M. Newcomb, R. Shen, S.-Y. Choi, P. H. Toy, P. F. Hollenberg, A. D. N. Vaz, M. J. Coon, J. Am. Chem. Soc. 2000, 122, 2677-2686.
17. P. H. Toy, M. Newcomb, P. F. Hollenberg, J. Am. Chem. Soc. 1998, 120, 7719-7729.
18. M. Newcomb, M.-H. Le Tadic-Biadatti, D. L. Chestney, E. S. Roberts, P. F. Hollenberg, J. Am. Chem. Soc. 1995, 117, 12085-12091.
19. M. Newcomb, M.-H. Le Tadic, D. A. Putt, P. F. Hollenberg, J Am. Chem. Soc. 1995, 117, 3312-3313.
20. M. Newcomb, R. Shen, Y. Lu, M. J. Coon, P. F. Hollenberg, D. A. Kopp, S. J. Lippard, J. Am. Chem. Soc. 2002, 124, 6879-6886.
21. K. Auclaire, Z. Hu, D. M. Little, P. R. Ortiz de Montellano, J. T. Groves, J. Am. Chem. Soc. 2002, 124, 6020-6027.
22. N. Suzuki, T. Higuchi, T. Nagano, J. Am. Chem. Soc. 2002, 124, 9622-9628.
23. F. Ogliaro, N. Harris, S. Cohen, M. Filatov, S. P. de Visser, S. Shaik, J. Am. Chem. Soc. 2000, 122, 8977-8989.
24. N. Harris, S. Cohen, M. Filatov, F. Ogliaro, S. Shaik, Angew. Chem. Int. Ed. 2000, 39, 2003-2007.
25. S. P. de Visser, F. Ogliaro, N. Harris, S. Shaik, J. Am. Chem. Soc 2001, 123, 3037-3047.
26. S. Shaik, S. P. de Visser, F. Ogliaro, H. Schwarz, D. Schröder, Curr. Opin. Chem. Biol. 2002, 6, 556-567.
27. S. P. de Visser, F. Ogliaro, P. K. Sharma, S. Shaik, J. Am. Chem. Soc. 2002, 124, 11809-11826.
28. P. K. Sharma, S. P. de Visser, F. Ogliaro, S. Shaik, J. Am. Chem. Soc 2003, 125, 2291-2300.
29. K. Yoshizawa, Y. Kagawa, Y. Shiota, J. Phys. Chem. B 2000, 104, 12365-12370.
30. K. Yoshizawa, T. Kamachi, Y. Shiota, J. Am. Chem. Soc. 2001, 123, 9806-9816.
31. T. Kamachi, K. Yoshizawa, J. Am. Chem. Soc. 2003, 125, 4652-4661.
32. V. Guallar, B. F. Gherman, W. H. Miller, S. J. Lippard, R. A. Friesner, J. Am. Chem. Soc. 2002, 124, 3377-3384.
33. S. Shaik, M. Filatov, D. Schröder, H. Schwarz, Chem. Eur J. 1998, 4, 193-199.
34. F. Ogliaro, S. Cohen, M. Filatov, N. Harris, S. Shaik, Angew. Chem. 2000, 112, 4009-4013; Angew. Chem. Int. Ed. 2000, 39, 3851-3855. Erratum: Angew. Chem. Int. Ed. 2001, 40, 647.
35. F. Ogliaro, S. Cohen, M. Filatov, N. Harris, S. Shaik, Angew. Chem. 2000, 112, 4009-4013; Angew. Chem. Int. Ed. 2000, 39, 3851-3855. Erratum: Angew. Chem. Int. Ed. 2001, 40, 647.
36. F. Ogliaro, S. Cohen, M. Filatov, N. Harris, S. Shaik, Angew. Chem. 2000, 112, 4009-4013; Angew. Chem. Int. Ed. 2000, 39, 3851-3855. Erratum: Angew. Chem. Int. Ed. 2001, 40, 647.
37. D. L. Harris, Curr. Opin. Chem. Biol. 2001, 5, 724-735.
38. M. T. Green, J. Am. Chem. Soc. 1999, 121, 7939-7940.
39. J. K. Atkinson, P. F. Hollenberg, K. U. Ingold, C. C. Johnson, M.-H. Le Tadic, M. Newcomb, D. A. Putt, Biochemistry 1994, 33, 10630-10637.
40. M. Newcomb, D. Aebisher, R. Shen, R. Esala, P. Chandrasena, P. F. Hollenberg, M. J. Coon, J. Am. Chem. Soc. 2003, 125, 6064-6065.
41. F. Ogliaro, S. P. de Visser, S. Cohen, P. K. Sharma, S. Shaik, J. Am. Chem. Soc. 2002, 124, 2806-2817.
42. P. K. Sharma, S. P. de Visser, S. Shaik, J. Am. Chem. Soc. 2003, 125, 8698-8699.
43. R. Davydov, T. M. Makris, V. Kofman, D. E. Werst, S. G. Sligar, B. M. Hoffman, J. Am. Chem. Soc. 2001, 123, 1403-1415.
44. S. Jin, T. M. Markis, T. A. Bryson, S. G. Sligar, J. H. Dawson, J Am. Chem. Soc. 2003, 125, 3406-3407.
45. F. Hino, D. Dolphin, Chem. Commun. 1999, 629-630.
46. T. G. Traylor, K. W. Hill, W.-P. Fann, S. Tsuchiya, B. E. Dunlap, J. Am. Chem. Soc. 1992, 114, 1308-1312.
47. F. Ogliaro, M. Filatov, S. Shaik, Eur. J. Inorg. Chem. 2000, 2455-2458.
48. J. C. Schöneboom, H. Lin, N. Reuter, W. Thiel, S. Cohen, F. Ogliaro, S. Shaik, J. Am. Chem. Soc. 2002, 124, 8142-8151.
49. M. Filatov, N. Harris, S. Shaik, Angew. Chem. 1999, 111, 3730-3733; Angew. Chem. Int. Ed. 1999, 38, 3510-3512.
50. M. Filatov, N. Harris, S. Shaik, Angew. Chem. 1999, 111, 3730-3733; Angew. Chem. Int. Ed. 1999, 38, 3510-3512.
51. M. T. Green, EXAFS data presented at the 12th International Conference on Cytochrome P450, La Grande Motte, France, September 11-15, 2001.
52. S. P. de Visser, F. Ogliaro, P. K. Sharma, S. Shaik, Angew. Chem. Int. Ed. 2002, 41, 1947-1951.
53. J. T. Groves, Z. Gross, M. K. Stern, Inorg. Chem. 1994, 33, 5065-5072.
54. Z. Gross, S. Nimri, C. M. Barzilay, L. Simkhovich, J. Biol. Inorg. Chem. 1997, 2, 492-506.
55. J. C. Schöneboom, S. Cohen, H. Lin, S. Shaik, W. Thiel, manuscript in preparation.
56. F. Ogliaro, S. P. de Visser, S. Cohen, J. Kaneti, S. Shaik, ChemBioChem 2001, 2, 848-851.
57. P. E. M. Siegbahn, R. H. Crabtree, J. Am. Chem. Soc. 1997, 119, 3103-3113.
58. M. Torrent, D. G. Musaev, H. Basch, K. Morokuma, J. Comp. Chem. 2002, 23, 59-76.
59. E. J. Mueller, P. J. Loida, S. G. Sligar, in Cytochrome P450. Structure, Mechanism and Biochemistry (Ed.: P. R. Ortiz de Montellano) 2nd ed., Plenum Press, New York, 1995, pp 83-124.
60. K. E. Liu, C. C. Johnson, M. Newcomb, S. J. Lippard, J. Am. Chem. Soc. 1993, 115, 939-947.
61. S. P. de Visser, F. Ogliaro, S. Shaik, Angew. Chem. Int. Ed. 2001; 40, 2871-2874.
62. J. T. Groves, J. Chem. Educ. 1985, 62, 928-931.
63. A. H. C. Horn, T. Clark, J. Am. Chem. Soc. 2003, 125, 2809-2816.
64. D. Kumar, S. P. de Visser, S. Shaik, J. Am. Chem. Soc. 2003, 125, 13024-13025.
65. S. Shaik, A. Shurki, Angew. Chem. Int. Ed. 1999, 38, 586-625; Angew. Chem. 1999, 11, 616-657.
66. S. Shaik, A. Shurki, Angew. Chem. Int. Ed. 1999, 38, 586-625; Angew. Chem. 1999, 11, 616-657.
67. D. Kumar, S. P. de Visser, P. K. Sharma, S. Cohen, S. Shaik, J. Am. Chem. Soc., in press.
68. F. Ogliaro, S. P. de Visser, S. Shaik, J. Inorg. Biochem. 2002; 91, 554-567.
69. F. Ogliaro, S. P. de Visser, J. T. Groves, S. Shaik, Angew. Chem. Int. Ed. 2001, 40, 2874-2878.
70. T. L. Poulos, J. Biol. Inorg. Chem. 1996, 1, 356-359.
71. F. Ogliaro, S. Cohen, S. P. de Visser, S. Shaik, J. Am. Chem. Soc. 2000, 122, 12892-12893.
72. P. H. Toy, M. Newcomb, M. J. Coon, A. D. N. Vaz, J. Am. Chem. Soc. 1998, 120, 9718-9719.
73. H. I. Liu, M. Sono, S. Kadkhodayan, L. P. Hager, B. Hedman, K. O. Hodgson, J. H. Dawson, J. Biol. Chem. 1995, 270, 10544-10550.
74. T. Kamachi, Y. Shiota, T. Ohta, K. Yoshizawa, Bull. Chem. Soc. Jpn. 2003, 76, 721-732.
75. S. P. de Visser, S. Shaik, J. Am. Chem. Soc. 2003, 125, 7413-7424.
76. Jaguar 4.1, Schrödinger, Inc., Portland, OR, 1991-2000.
77. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Mil. lam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Gaussian, Inc., Pittsburgh PA, 1998.
78. D. Danovich, "Green's Function Method in Semiempirical Molecular Orbital Theory: Calculations of Ionization Potentials and Electron Affinities", in Encyclopedia of Computational Chemistry (Eds.: P. v. R. Schleyer, N. L. Allinger, T. Clark, J. Gasteiger, P. A. Kollman, H. F. Schaefer III), John Wiley & Sons, 1998, vol. 2, p. 1190-1202.
79. D. Danovich, Y. Apeloig, S. Shaik, J. Chem. Soc., Perkin Trans. 2 1993, 321-329.