Hydroxylation by the Hydroperoxy-Iron Species in Cytochrome P450 Enzymes

Journal of the American Chemical Society

Volumn 126, Issue 1, 2004, Pages 115-126

  Chandrasena, R Esala P ^a   Vatsis, Kostas P ^b   Coon, Minor J ^b   Hollenberg, Paul F ^b   Newcomb, Martin ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; HYDROGEN PEROXIDE; HYDROXYLATION; OXIDATION; RATE CONSTANTS; STEREOCHEMISTRY;

KINETIC ISOTOPE EFFECTS (KIE);

ENZYMES;

1 (4 TRIFLUOROMETHYLPHENYL)BUT 3 EN 1 OL; 2 (4 TRIFLUOROMETHYLPHENYL)CYCLOPROPYLMETHANE; 2 (4 TRIFLUOROMETHYLPHENYL)CYCLOPROPYLMETHANOL; CYTOCHROME P450; CYTOCHROME P450 2B1; CYTOCHROME P450 DELTA 2B4; CYTOCHROME P450 DELTA 2B4 T302A; CYTOCHROME P450 DELTA 2E1; CYTOCHROME P450 DELTA 2E1 T303A; DEUTERIUM; HYDROGEN PEROXIDE; HYDROPEROXIDE; IRON; METHYL GROUP; ORGANOFLUORINE DERIVATIVE; OXIDIZING AGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PARAMETERS; CHEMICAL REACTION KINETICS; ENANTIOMER; ENZYME SUBSTRATE COMPLEX; HYDROXYLATION; KINETIC ISOTOPE EFFECT; OXIDATION; TEMPERATURE;

EID: 0346499298     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038237t     Document Type: Article

References (60)

1. Ortiz de Montellano, P. R., Ed. Cytochrome P450 Structure, Mechanism, and Biochemistry, 2nd ed.; Plenum: New York, 1995.
2. White, R. E.; Coon, M. J. Annu. Rev. Biochem. 1980, 49, 315-356.
3. Davydov, R.; Macdonald, I. D. G.; Makris, T. M.; Sligar, S. G.; Hoffman, B. M. J. Am. Chem. Soc. 1999, 121, 10654-10655.
4. Davydov, R.; Makris, T. M.; Kofman, V.; Werst, D. E.; Sligar, S. G.; Hoffman, B. M. J. Am. Chem. Soc. 2001, 123, 1403-1415.
5. Egawa, T.; Shimada, H.; Ishimura, Y. Biochem. Biophys. Res. Commun. 1994, 201, 1464-1469.
6. Kellner, D. G.; Hung, S. C.; Weiss, K. E.; Sligar, S. G. J. Biol. Chem. 2002, 277, 9641-9644.
7. Nordblom, G. D.; White, R. E.; Coon, M. J. Arch. Biochem. Biophys. 1976, 175, 524-533.
8. Newcomb, M.; Le Tadic-Biadatti, M. H.; Chestney, D. L.; Roberts, E. S.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 12085-12091.
9. Toy, P. H.; Dhanabalasingam, B.; Newcomb, M.; Hanna, I. H.; Hollenberg, P. F. J. Org. Chem. 1997, 62, 9114-9122.
10. Vaz, A. D. N.; McGinnity, D. F.; Coon, M. J. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 3555-3560.
11. Toy, P. H.; Newcomb, M.; Coon, M. J.; Vaz, A. D. N. J. Am. Chem. Soc. 1998, 120, 9718-9719.
12. Newcomb, M.; Shen, R.; Choi, S. Y.; Toy, P. H.; Hollenberg, P. F.; Vaz, A. D. N.; Coon, M. J. J. Am. Chem. Soc. 2000, 122, 2677-2686.
13. Pratt, J. M.; Ridd, T. I.; King, L. J. J. Chem. Soc., Chem. Commun. 1995, 2297-2298.
14. Jin, S. X.; Makris, T. M.; Bryson, T. A.; Sligar, S. G.; Dawson, J. H. J. Am. Chem. Soc. 2003, 125, 3406-3407.
15. Newcomb, M.; Coon, M. J.; Hollenberg, P. F. Arch. Biochem. Biophys. 2003, 409, 72-79.
16. Shaik, S.; Filatov, M.; Schroder, D.; Schwarz, H. Chem.-Eur. J. 1998, 4, 193-199.
17. Guallar, V.; Baik, M.-H.; Lippard, S. J.; Friesner, R. A. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 6998-7002.
18. cam (ca. 6000 atoms MM. ca. 130 atoms QM) found considerable electronic differences for spin states when the P450 model included hydrogen-bonded carboxylates on the macrocycle. The spin shifts, which bias the energies of the spin states, are a fundamental consequence of including a larger portion of the enzyme in the QM model.17
19. Newcomb, M.; Acbisher, D.; Shen, R.; Chandrasena, R. E. P.; Hollenberg, P. F.; Coon, M. J. J. Am. Chem. Soc. 2003, 125, 6064-6065.
20. Atkinson, J. K.; Hollenberg, P. F.; Ingold, K. U.; Johnson, C. C.; Le Tadic, M. H.; Newcomb, M.; Putt, D. A. Biochemistry 1994, 33, 10630-10637.
21. Chandrasena, R. E. P.; Newcomb, M.; Surve, B. C.; Wink, D. J., unpublished results.
22. Hanna, I. H.; Teiber, J. F.; Kokones, K. L.; Hollenberg, P. F. Arch. Biochem. Biophys. 1998, 350, 324-332.
23. Vaz, A. D.; Pernecky, S. J.; Raner, G. M.; Coon, M. J. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 4644-4648.
24. Toy, P. H.; Newcomb, M.; Hollenberg, P. F. J. Am. Chem. Soc. 1998, 120, 7719-7729.
25. Masking and unmasking are briefly discussed in the Appendix in the Supporting Information.
26. For an overview of masking effects in P450-catalyzed reactions, see: Higgins, L.; Bennett, G. A.; Shimoji, M.; Jones, J. P. Biochemistry 1998, 37, 7039-7046.
27. Kwart, H. Acc. Chem. Res. 1982, 15, 401-408.
28. Vatsis, K. P.; Peng, H. M.; Coon, M. J. J. Inorg. Biochem. 2002, 91, 542-553.
29. Vatsis, K. P.; Coon, M. J., unpublished results.
30. Roberts, E. S.; Ballou, D. P.; Hopkins, N. E.; Alworth, W. L.; Hollenberg, P. F. Arch. Biochem. Biophys. 1995, 323, 303-312.
31. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921.
32. Newcomb, M.; Choi, S. Y.; Toy, P. H. Can. J. Chem. 1999, 77, 1123-1135.
33. Wiberg, K. B.; Shobe, D.; Nelson, G. L. J. Am. Chem. Soc. 1993, 115, 10645-10652.
34. Park, J. Y.; Harris, D. J. Med. Chem. 2003, 46, 1645-1660.
35. Hanzlik, R. P.; Hogberg, K.; Moon, J. B.; Judson, C. M. J. Am. Chem. Soc. 1985, 107, 7164-7167.
36. Jones, J. P.; Rettie, A. E.; Trager, W. F. J. Med. Chem. 1990, 33, 1242-1246.
37. Ogliaro, F.; Filatov, M.; Shaik, S. Eur. J. Inorg. Chem. 2000, 2455-2458.
38. Kumar, D.; de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2003, 125, 13024-13025.
39. 3) and found a range of KIE ratios from 1.4 to 2.3 with an average of 1.75 for 10 examples of enzymes and substrate (Newcomb, M.; Chandrasena, R. E. P., unpublished results).
40. Harris, D. L.; Loew, G. H. J. Am. Chem. Soc. 1998, 120, 8941-8948.
41. Le Tadic-Biadatti, M. H.; Newcomb, M. J. Chem. Soc., Perkin Trans. 2 1996, 1467-1473.
42. Newcomb, M.; Toy, P. H. Acc. Chem. Res. 2000, 33, 449-455.
43. Newcomb, M.; Shen, R. N.; Lu, Y.; Coon, M. J.; Hollenberg, P. F.; Kopp, D. A.; Lippard, S. J. J. Am. Chem. Soc. 2002, 124, 6879-6886.
44. Auclair, K.; Hu, Z.; Little, D. M.; Ortiz de Montellano, P. R.; Groves, J. T. J. Am. Chem. Soc. 2002, 124, 6020-6027.
45. Coon, M. J. Biochem. Biophys. Res. Commun. 2003, 312, 163-168.
46. Volz, T. J.; Rock, D. A.; Jones, J. P. J. Am. Chem. Soc. 2002. 124, 9724-9725.
47. Hutzler, J. M.; Powers, F. J.; Wynalda, M. A.; Wienkers, L. C. Arch. Biochem. Biophys. 2003, 417, 165-175.
48. Jones, J. P.; Trager, W. F. J. Am. Chem. Soc. 1987, 109, 2171-2173.
49. Correction: 1988, 110, 2018.
50. Halgren, T. A.; Roberts, J. D.; Horner, J. H.; Martinez, F. N.; Tronche, C.; Newcomb, M. J. Am. Chem. Soc. 2000, 122, 2988-2994.
51. Sorokin, A.; Robert, A.; Meunier, B. J. Am. Chem. Soc. 1993, 115, 7293-7299.
52. Ortiz de Montellano, P. R. Acc. Chem. Res. 1998, 31, 543-549.
53. Kamaraj, K.; Bandyopadhyay, D. J. Am. Chem. Soc. 1997, 119, 8099-8100.
54. Nam, W.; Lim, M. H.; Moon, S. K.; Kim, C. J. Am. Chem. Soc. 2000, 122, 10805-10809.
55. Nam, W.; Lim, M. H.; Lee, H. J.; Kim, C. J. Am. Chem. Soc. 2000, 122, 6641-6647.
56. Collman, J. P.; Chien, A. S.; Eberspacher, T. A.; Brauman, J. I. J. Am. Chem. Soc. 2000, 122, 11098-11100.
57. Wadhwani, P.; Mukherjee, M.; Bandyopadhyay, D. J. Am. Chem. Soc. 2001, 123, 12430-12431.
58. Collman, J. P.; Zeng, L.; Decréau, R. A. Chem. Commun. 2003, 2974-2975.
59. Zhang, X.; Hodgetts, K.; Rachwal, S.; H., Z.; Wasley, J. W. F.; Craven, K.; Brodbeck, R.; Kieltyka, A.; Hoffman, D.; Bacolod, M. D.; Girard, B.; Tran, J.; Thurkauf, A. J. Med. Chem. 2000, 43, 3923-3932.
60. Vatsis, K. P.; Coon, M. J. Arch. Biochem. Biophys. 2002, 397, 119-129.