Aromatic Hydroxylation by Cytochrome P450: Model Calculations of Mechanism and Substituent Effects

Journal of the American Chemical Society

Volumn 125, Issue 49, 2003, Pages 15004-15005

  Bathelt, Christine M ^a   Ridder, Lars ^a,b   Mulholland, Adrian J ^a   Harvey, Jeremy N ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b NV ORGANON   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450;

ARTICLE; BIOTRANSFORMATION; CALCULATION; ENZYME MECHANISM; HYDROXYLATION; ION TRANSPORT; MOLECULAR MODEL; OXIDATION;

CYTOCHROME P-450 ENZYME SYSTEM; HYDROCARBONS, AROMATIC; HYDROXYLATION; MODELS, MOLECULAR; THERMODYNAMICS;

EID: 0344236096     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035590q     Document Type: Article

References (37)

1. Guengerich, F. P. Chem. Res. Toxicol. 2001, 14, 611-650.
2. Anzenbacher, P.; Anzenbacherova, E. Cell. Mol. Life Sci. 2001, 58, 737.
3. Ridder, L.; Harvey, J. N.; Rietjens, I. M. C. M.; Vervoort, J.; Mulholland, A. J. J. Phys. Chem. B 2003, 107, 2118-2126 and references therein.
4. Bathelt, C.; Schmid, R. D.; Pleiss, J. J. Mol. Model. 2002, 8, 327.
5. White, R. E.; McCarthy, M.; Egeherg, K. D.; Sligar, S. G. Arch. Biochem. Biophys. 1984, 228, 493-502.
6. (a) Newcomb, M.; Hollenberg P. F.; Coon, M. J. Arch. Biochem. Biophys. 2003, 409, 72-79.
7. (b) Manchester, J. I.; Dinnocenzo, J. P.; Higgins, L. A.; Jones, J. P. J. Am. Chem. Soc. 1997, 119, 5069-5070.
8. (a) Ogliaro, F.; Harris, N.; Cohen, S.; Filatov, M.; de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2000, 122, 8977-8989.
9. (h) Yoshizawa, K.; Kamachi, T.; Shiota, Y. J. Am. Chem. Soc. 2001, 123, 9806-9816.
10. (c) de Visser, S. P.; Ogliaro, F.; Harris, N.; Shaik, S. J. Am. Chem. Soc. 2001, 123, 3037-3047.
11. (d) de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. J. Am. Chem. Soc. 2002, 124, 11809-11826.
12. (e) Kamachi, T.; Yoshizawa, K. J. Am. Chem. Soc. 2003, 125, 4652-4661.
13. (f) Guallar, V.; Baik, M.-H.; Lippard, S. J.; Friesner, R. A. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 6998.
14. Korzekwa, K. R.; Swinney, D. C.; Trager, W. F. Biochemistry 1989, 28, 9019-9027.
15. Korzekwa, K.; Trager, W.; Gouterman, M.; Spangler, D.; Loew, G. H. J. Am. Chem. Soc. 1985, 107, 4273-4279.
16. (a) Zakharieva, O.; Grodzicki, M.; Trautwein, A. X.; Veeger, C.; Rietjens, I. M. C. M. J. Biol. Inorg. Chem. 1996, 1, 192-204.
17. (b) Zakharieva, O.; Grodzicki, M.; Trautwein, A. X.; Veeger, C.; Rietjens, I. M. C. M. Biophys. Chem. 1998, 73, 189-203.
18. Calculations were carried out with the Jaguar 4.2 software (Schrödinger, Inc., Portland, OR, 1991-2002) using the unrestricted hybrid density functional UB3LYP. Geometry optimizations were performed using the standard Los Alamos effective core potential and associated triple-η basis set on Fe (LACV3P basis), and the 6-31G* basis on all other atoms (BS I). Energies in Figure 2 are based on single-point calculations at optimized geometries performed with the same LACV3P basis on Fe, but the larger 6-311 +G** basis on other atoms (BS II).
19. Harvey, J. N. J. Am. Chem. Soc. 2000, 122, 12401-12402.
20. Siegbahn, P. E. M. Q. Rev. Biophys. 2003, 36, 91-145.
21. Siegbahn, P. E. M.; Blomberg M. R. A. Chem. Rev. 2000, 100, 421-437.
22. (a) Harris, L. H.; Loew, G. H. J. Am. Chem. Soc. 1998, 120, 8941-8948.
23. (b) Shaik, S.; de Visser, S. P.; Ogliaro, F.; Schwarz, H.; Schröder, D. Curr. Opin. Chem. Biol. 2002, 6, 556-567.
24. (a) Guroff, G.; Daly, J. W.; Jerina, D. M.; Renson, J.; Witcop, B.; Udenfriend, S. Science 1967, 157, 1524-1530.
25. (b) Koerts, J.; Soffers, A. E. M. F.; Vervoort, J.; De Jager, A.; Rietjens, I. M. C. M. Chem. Res. Toxicol. 1998, 11, 503-512.
26. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
27. Hansch, C.; Gao, H. Chem. Rev. 1997, 97, 2995-3059.
28. Dinctuerk, S.; Jackson, R. A. J. Chem. Soc., Perkin Trans. 2 1981, 1127-1131.
29. Taylor, R. Electrophilic aromatic substitution; Wiley: Chichester, 1990; pp 458-463.
30. Burka, L. T.; Plucinski, T. M.; MacDonald, T. L. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 6680-6684.
31. (a) Rietjens, I. M. C. M.; Soffers, A. E. M. F.; Veeger, C.; Vervoort, J. Biochemistry 1993, 32, 4801-4812.
32. (b) Cnubben, N. H. P.; Peelen, S.; Borst, J.-W.; Vervoort, J.; Veeger, C.; Rietjens, I. M. C. M. Chem. Res. Toxicol. 1994, 7, 590-598.
33. Safari, N.; Bahadoran F.; Mohammed, R. H.; Ghiasi R. J. Porphyrins Phthalocyanines 2000, 4, 285-291.
34. (a) Higgins, L. A.; Korzekwa, K. R.; Rao, S.; Shou, M.; Jones, J. P. Arch. Biochem. Biophys. 2001, 385, 220-230.
35. (h) Jones, J. P.; Mysinger, M.; Korzekwa, K. R. Drug Metab. Dispos. 2002, 30, 7-12.
36. Soffers, A. E. M. F.; Boersma, M. G.; Vaes, W. H. J.; Vervoort, J.; Tyrakowska, B.; Hermens, J. L. M.; Rietjens, I. M. C. M. Toxicology in Vitro 2001, 15, 539-551.
37. After submission of this paper, a related study of the mechanism of oxidation of benzene appeared, with somewhat similar conclusions (de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2003, 125, 7413-7424.)