Kinetic isotope effects in a C-H bond dissociation by the iron-oxo species of cytochrome P450

Journal of Physical Chemistry B

Volumn 104, Issue 51, 2000, Pages 12365-12370

  Yoshizawa, Kazunari ^a   Kagawa, Yoshihisa ^a   Shiota, Yoshihito ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DISSOCIATION; ETHANE; HYDROGEN BONDS; HYDROXYLATION; IRON COMPOUNDS; ISOTOPES;

CYTOCHROME; KINETIC ISOTOPE EFFECTS (KIE);

PORPHYRINS;

EID: 0034352128     PISSN: 10895647     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp001950+     Document Type: Article

References (41)

1. (a) Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1995.
2. (b) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841.
3. Hjelmeland, L. M.; Aronow, L.; Trudell, J. R. Biochem. Biophys. Res. Commun. 1977, 76, 541.
4. Groves, J. T.; McClusky, G. A.; White, R. E.; Coon, M. J. Biochem. Biophys. Res. Commun. 1978, 81, 154.
5. (a) White, R. E.; Coon, M. J. Annu. Rev. Biochem. 1980, 49, 315.
6. (b) Guengerich, F. P.; Macdonald, T. L. FASEB J. 1990, 4, 2453.
7. (c) Woggon, W. D.; Fretz, H. In Advances in Detailed Reaction Mechanism; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1992; Vol. 2, p 111.
8. Groves, J. T. J. Chem. Educ. 1985, 62, 928.
9. (a) Newcomb, M.; Le Tadic-Biadatti, M.-H.; Chestney, D. L.; Roberts, E. S.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 12085.
10. (b) Toy, P. H.; Newcomb, M.; Hollenberg, P. F. J. Am. Chem. Soc. 1998, 120, 7719.
11. (c) 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.
12. (a) Harris, D. L.; Loew, G.; Waskell, L. J. Am. Chem. Soc. 1998, 120, 4308.
13. (b) Harris, D. L.; Loew, G. J. Am. Chem. Soc. 1998, 120, 8941.
14. (c) Green, M. T. J. Am. Chem. Soc. 1998, 120, 10772.
15. (d) Green, M. T. J. Am. Chem. Soc. 1999, 121, 7939.
16. (a) Shaik, S.; Filatov, M.; Schröder, D.; Schwarz, H. Chem. Eur. J. 1998, 4, 193.
17. (b) Filatov, M.; Harris, N.; Shaik, S. J. Chem. Soc., Perkin Trans. 2 1999, 399.
18. (c) Filatov, M.; Harris, N.; Shaik, S. Angew. Chem., Int. Ed. Engl. 1999, 38, 3510.
19. Siegbahn, P. E. M.; Crabtree, R. H. J. Am. Chem. Soc. 1997, 119, 3103.
20. Yoshizawa, K.; Shiota, Y.; Kagawa, Y. Bull. Chem. Soc. Jpn., in press.
21. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
22. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
23. Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829.
24. Dunning, T. H.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; Vol. 3, p 1.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian Inc.: Pittsburgh, PA, 1998.
26. McQuarrie, D. A. Statistical Thermodynamics; University Science Books: Mill Valley, 1973.
27. Wigner, E. J. Chem. Phys. 1937, 5, 720.
28. Ohta, T.; Matsuura, K.; Yoshizawa, K.; Morishima, I. J. Inorg. Biochem., in press.
29. Loew, G. H.; Harris, D. L. Chem. Rev. 2000, 100, 407.
30. Schlichting, I.; Berendzen, J.; Chu, K.; Stock, A. M.; Maves, S. A.; Benson, D. E.; Sweet, R. M.; Ringe, D.; Petsko, G. A.; Sugar, S. G. Science 2000, 287, 1615.
31. Gross, Z.; Nimri, S.; Barzilay, C. M.; Simkhovich, L. J. Biol. Inorg. Chem. 1997, 2, 492.
32. Groves, J. T.; Gross, Z.; Stern, M. K. Inorg. Chem. 1994, 33, 5065.
33. (a) Yoshizawa, K.; Shiota, Y.; Yamabe, T. Chem. Eur. J. 1997, 3, 1160.
34. (b) Yoshizawa, K.; Shiota, Y.; Yamabe, T. J. Am. Chem. Soc. 1998, 120, 564.
35. (c) Yoshizawa, K.; Shiota, Y.; Yamabe, T. Organometallics 1998, 17, 2825.
36. We could not find the transition state for the rebound step despite our best efforts. Thus, the barrier height for this electronic process should be very small even if it exists on the reaction pathway.
37. (a) Shaik, S.; Danovich, D.; Fiedler, A.; Schröder, D.; Schwarz, H. Helv. Chim. Acta 1995, 78, 1393.
38. (b) Schröder, D.; Shaik, S.; Schwarz, H. Acc. Chem. Res. 2000, 33, 139.
39. Harris, N.; Cohen, S.; Filatov, M.; Ogliaro, F.; Shaik, S. Angew. Chem., Int. Ed. Engl. 2000, 39, 2003.
40. Manchester, J. I.; Dinnocenzo, J. P.; Higgins, L.-A.; Jones, J. P. J. Am. Chem. Soc. 1997, 119, 5069.
41. Yoshizawa, K.; Shiota, Y.; Kagawa, Y.; Yamabe, T. J. Phys. Chem. A 2000, 104, 2552.