Peripheral heme substituents control the hydrogen-atom abstraction chemistry in cytochromes P450

Proceedings of the National Academy of Sciences of the United States of America

Volumn 100, Issue 12, 2003, Pages 6998-7002

  Guallar, Victor ^a   Baik, Mu Hyun ^a   Lippard, Stephen J ^b   Friesner, Richard A ^a  

^a Columbia University ^*  (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHOR; CYTOCHROME P450; HEME; HYDROGEN; METALLOPROTEIN;

ARTICLE; CATALYSIS; ENERGY TRANSFER; ENZYME ACTIVE SITE; ENZYME MECHANISM; ENZYME STABILITY; HYDROXYLATION; MOLECULAR INTERACTION; MOLECULAR MECHANICS; PRIORITY JOURNAL; QUANTUM MECHANICS;

CAMPHOR; CYTOCHROME P-450 ENZYME SYSTEM; ELECTROSTATICS; HEME; HYDROGEN; HYDROXYLATION; MODELS, MOLECULAR; OXIDATION-REDUCTION; PROTEIN CONFORMATION; THERMODYNAMICS;

DRYOBALANOPS;

EID: 0038472409     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0732000100     Document Type: Article

References (29)

1. Ortiz de Montellano, P. R. (1995) Cytochrome P450: Structure, Mechanism and Biochemistry (Plenum, New York).
2. Benson, D. E., Suslick, K. S. & Sligar, S. G. (1997) Biochemistry 36, 5104-5107.
3. Aikens, J. & Sligar, S. G. (1994) J. Am. Chem. Soc. 116, 1143-1144.
4. Davydov, R., Kappl, R., Huttermann, J. & Peterson, J. A. (1991) FEBS Lett. 295, 113-115.
5. Davydov, R., Makris, T. M., Kofman, V., Werst, D. E., Sligar, S. G. & Hoffman, B. M. (2001) J. Am. Chem. Soc. 123, 1403-1415.
6. Dawson, J. H., Kau, L. S., Penner-Hahn, J. E., Sono, M., Eble, K. S., Bruce, G. S., Hager, L. P. & Hodgson, K. O. (1986) J. Am. Chem. Soc. 108, 8114-8116.
7. Egawa, T., Shimada, H. & Ishimura, Y. (1994) Biochem. Biophys. Res. Commun. 201, 1464-1469.
8. Guallar, V., Harris, D. L., Batista, V. S. & Miller, W. H. (2002) J. Am. Chem. Soc. 124, 1430-1437.
9. Harris, D. L. & Loew, G. H. (1998) J. Am. Chem. Soc. 120, 8941-8948.
10. Jones, J. P., Rettie, A. E. & Trager, W. F. (1990) J. Med. Chem. 33, 1242-1246.
11. Loew, G. H. & Harris, D. L. (2000) Chem. Rev. (Washington, D.C.) 100, 407-419.
12. Roitberg, A. E., Holden, M. J., Mayhew, M. P., Kurnikov, I. V., Beratan, D. N. & Vilker, V. L. (1998) J. Am. Chem. Soc. 120, 8927-8932.
13. Schappacher, M., Ricard, L., Fischer, J., Weiss, R., Bill, E., Montielmontoya, R., Winkler, H. & Trautwein, A. X. (1987) Eur. J. Biochem. 168, 419-429.
14. Schlichting, I., Berendzen, J., Chu, K., Stock, A. M., Maves, S. A., Benson, D. E., Sweet, R. M., Ringe, D., Petsko, G. A. & Sligar, S. G. (2000) Science 287, 1615-1622.
15. Sjodin, T., Christian, J. F., Macdonald, I. D. G., Davydov, R., Unno, M., Sligar, S. G., Hoffman, B. M. & Champion, P. M. (2001) Biochemistry 40, 6852-6859.
16. Toy, P. H., Newcomb, M. & Hollenberg, P. F. (1998) J. Am. Chem. Soc. 120, 7719-7729.
17. Guallar, V., Gherman, B. F., Miller, W. H., Lippard, S. J. & Friesner, R. A. (2002) J. Am. Chem. Soc. 124, 3377-3384.
18. Siegbahn, P. E. M., Crabtree, R. H. & Nordlund, P. (1998) J. Biol. Inorg. Chem. 3, 314-317.
19. Ogliaro, F., Harris, N., Cohen, S., Filatov, M., De Visser, S. P. & Shaik, S. (2000) J. Am. Chem. Soc. 122, 8977-8989.
20. Nam, W., Lim, M. H., Lee, H. J. & Kim, C. (2000) J. Am. Chem. Soc. 122, 6641-6647.
21. Ogliaro, F., De Visser, S. P., Cohen, S., Sharma, P. K. & Shaik, S. (2002) J. Am. Chem. Soc. 124, 2806-2817
22. Philipp, D. M. & Friesner, R. A. (1999) J. Comput. Chem. 20, 1468-1494.
23. Murphy, R. B., Philipp, D. M. & Friesner, R. A. (2000) J. Comput. Chem. 21, 1442-1457.
24. Schrödinger (2001) QSITE (Schrödinger, Portland, OR).
25. Kamachi, T. & Yoshizawa, K. (2003) J. Am. Chem. Soc. 125, 4652-4661.
26. Ogliaro, F., Cohen, S., De Visser, S. P. & Shaik, S. (2000) J. Am. Chem. Soc. 122, 12892-12893.
27. Marshall, P. (1999) J. Phys. Chem. A 103, 4560-4563.
28. Xu, Z. F., Li, S. M., Yu, Y. X., Li, Z. S. & Sun, C. C. (1999) J. Phys. Chem. A 103, 4910-4917.
29. Wirstam, M., Lippard, S. J. & Friesner, R. A. (2003) J. Am. Chem. Soc. 125, 3980-3987.