A single-site mutation (F429H) converts the enzyme CYP 2B4 Into a heme oxygenase: A QM/MM study

Journal of the American Chemical Society

Volumn 134, Issue 9, 2012, Pages 4053-4056

  Usharani, Dandamudi ^a   Zazza, Costantino ^b   Lai, Wenzhen ^a,d   Chourasia, Mukesh ^a   Waskell, Lucy ^c   Shaik, Sason ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b SCUOLA NORMALE SUPERIORE   (Italy)

^c UNIVERSITY OF MICHIGAN   (United States)

^d RENMIN UNIVERSITY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BOND ACTIVATION; BOND CLEAVAGES; CYTOCHROME P450; HEME OXYGENASES; HETEROLYTIC CLEAVAGE; QUANTUM MECHANICAL/MOLECULAR MECHANICAL CALCULATIONS; SINGLE RESIDUE; SINGLE-SITE MUTATIONS;

AMINO ACIDS; MOLECULAR MODELING; PORPHYRINS;

ENZYMES;

CYSTEINE; CYTOCHROME P450 2B4; HEME OXYGENASE; LIGAND; WATER;

ARTICLE; ENZYME ACTIVITY; HYDROGEN BOND; HYDROXYLATION; MOLECULAR MECHANICS; MUTANT; MUTATION; PROTON TRANSPORT;

ARYL HYDROCARBON HYDROXYLASES; HEME OXYGENASE (DECYCLIZING); MUTAGENESIS; MUTANT PROTEINS; MUTATION; QUANTUM THEORY;

EID: 84857893631     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja211905e     Document Type: Article

References (39)

1. (a) Cytochrome P450: Structure, Mechanism and Biochemistry, 3rd ed.; Ortiz de Montellano, P. R., Ed.; Kluwer: New York, 2004.
2. (b) Shaik, S.; Cohen, S.; Wang, Y.; Chen, H.; Kumar, D.; Thiel, W. Chem. Rev. 2010, 110, 949.
3. (a) Colas, C.; Ortiz de Montellano, P. R. Chem. Rev. 2003, 103, 2305.
4. (b) Unno, M.; Matsui, T.; Ikeda-Saito, M. Nat. Prod. Rep. 2007, 24, 553.
5. (c) Matsui, T.; Unno, M.; Ikeda-Saito, M. Acc. Chem. Res. 2010, 43, 240.
6. (a) Denisov, I. G.; Makris, T. M.; Sligar, S. G.; Schlichting, I. Chem. Rev. 2005, 105, 2253.
7. (b) Chen, H.; Moreau, Y.; Derat, E.; Shaik, S. J. Am. Chem. Soc. 2008, 130, 1953.
8. (a) Davydov, R.; Razeghifard, R.; Im, S.-C.; Waskell, L.; Hoffman, B. M. Biochemistry 2008, 47, 9661.
9. (b) Hamdane, D.; Xia, C.; Im, S.-C; Zhang, H.; Kim, J.-J. P.; Waskell, L. J. Biol. Chem. 2009, 284, 11374.
10. (a) Sherwood, P.; et al. THEOCHEM 2003, 632, 1.
11. (b) Brooks, B. R.; Burccoleri, R. E.; Olafson, B. D.; States, D. J.; Karplus, M. J. Comput. Chem. 1983, 4, 187.
12. (c) Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, C. Chem. Phys. Lett. 1989, 162, 165.
13. (d) Senn, H. M.; Thiel, W. Angew. Chem., Int. Ed. 2009, 48, 1198.
14. (e) Zheng, J.; Wang, D.; Thiel, W.; Shaik, S. J. Am. Chem. Soc. 2006, 128, 13204.
15. (f) Chen, H.; Hirao, H.; Derat, E.; Schlichting, I.; Shaik, S. J. Phys. Chem. B 2008, 112, 9490.
16. (a) Scott, E. E.; White, M. A.; He, Y. A.; Johnson, E. F.; Stout, C. D.; Halpert, J. R. J. Biol. Chem. 2004, 279, 27294.
17. (b) Zazza, C.; Amadei, A.; Palma, A.; Sanna, N.; Tatoli, S.; Aschi, M. J. Phys. Chem. B 2008, 112, 3184.
18. (a) Mak, P. J.; Im, S.-C.; Zhang, H.; Waskell, L.; Kincaid, J. R. Biochemistry 2008, 47, 3950.
19. (b) Mak, P. J.; Zhang, H.; Hollenberg, P. F.; Kincaid, J. R. J. Am. Chem. Soc. 2010, 132, 1494.
20. (a) Altarsha, M.; Benighaus, T.; Kumar, D.; Thiel, W. J. Am. Chem. Soc. 2009, 131, 4755.
21. (b) Sen, K.; Hackett, J. C. J. Phys. Chem. B. 2009, 113, 8170.
22. (a) Makris, T. M.; von Koeing, K.; Schlichting, I.; Sligar, S. G. Biochemistry 2007, 46, 14129.
23. (b) Vatsis, K. P.; Peng, H.-W.; Coon, M. J. J. Inorg. Biochem. 2002, 91, 542.
24. (c) Raag, R.; Poulous, T. Biochemistry 1989, 28, 7586.
25. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
26. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
27. (c) Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829.
28. (a) Poulos, T. L. J. Biol. Inorg. Chem. 1996, 1, 356.
29. (b) Yoshioka, S.; Takahashi, S.; Ishimori, K.; Morishima, I. J. Inorg. Biochem. 2000, 81, 141.
30. (c) Dawson, J. H. Science 1988, 240, 433.
31. (a) Ogliaro, F.; de Visser, S. P.; Shaik, S. J. Inorg. Biochem. 2002, 91, 554.
32. (b) Shaik, S.; Hirao, H.; Kumar, D. Nat. Prod. Rep. 2007, 24, 533.
33. (a) Cho, K.-B.; et al. J. Phys. Chem. A 2008, 112, 13128.
34. See the equation in Table S1 of: Lai, W. Z.; Chen, H.; Cho, K.-B.; Shaik, S. J. Phys. Chem. Lett. 2010, 1, 2082.
35. Perera, R.; Sono, M.; Kinloch, R.; Zhang, H.; Tarasev, M.; Im, S.-C.; Waskell, L.; Dawson, J. H. Biochim. Biophys. Acta 2011, 1814, 69.
36. Ost, T. W. B.; Miles, C. S.; Munro, A. W.; Murdoch, J.; Reid, G. A.; Chapman, S. K. Biochemistry 2001, 40, 13421.
37. For example, see: (a) Reference 3a and discussions therein.
38. (b) White, R. E.; Sligar, S. G.; Coon, M. J. J. Biol. Chem. 1980, 255, 11108.
39. (c) Shimizu, T.; Murakami, Y.; Hatano, M. J. Biol. Chem. 1994, 269, 13296.