A rational approach to re-engineer cytochrome P450 2B1 regioselectivity based on the crystal structure of cytochrome P450 2C5

Journal of Biological Chemistry

Volumn 278, Issue 19, 2003, Pages 17178-17184

  Kumar, Santosh ^a   Scott, Emily E ^b   Liu, Hong ^b   Halpert, James R ^b  

^a University of Texas Medical Branch School of Medicine   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST SELECTIVITY; CRYSTAL STRUCTURE; HYDROXYLATION; MUTAGENESIS;

REGIOSELECTIVITY;

BIOCHEMISTRY;

CYTOCHROME P450 2B1; CYTOCHROME P450 2C5; PROGESTERONE; PROGESTERONE 16ALPHA HYDROXYLASE; PROGESTERONE 21 MONOOXYGENASE; UNCLASSIFIED DRUG; RECOMBINANT PROTEIN; STEROID MONOOXYGENASE;

ARTICLE; COMPUTER MODEL; CRYSTAL STRUCTURE; ENZYME PURIFICATION; ENZYME STRUCTURE; ESCHERICHIA COLI; GENE MUTATION; HYDROXYLATION; NONHUMAN; PRIORITY JOURNAL; SITE DIRECTED MUTAGENESIS; ANIMAL; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY; GENETICS; MUTATION; PROTEIN CONFORMATION; RABBIT; RAT; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

ESCHERICHIA COLI;

ANIMALS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; CYTOCHROME P-450 CYP2B1; HYDROXYLATION; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; MUTATION; PROTEIN CONFORMATION; RABBITS; RATS; RECOMBINANT PROTEINS; STEROID HYDROXYLASES; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 0037931781     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M212515200     Document Type: Article

References (47)

1. Williams, P. A., Cosme, J., Sridhar, V., Johnson, E. F., and McRee, D. E. (2000) Mol. Cell 5, 121-131
2. Domanski, T. L., and Halpert, J. R. (2001) Curr. Drug Metab. 2, 117-137
3. Gotoh, O. (1992) J. Biol. Chem. 267, 83-90
4. Haseman, C. A., Kurumbail, R. G., Boddupalli, S. S., Peterson, J. A., and Deisenhofer, J. (1995) Structure 3, 41-62
5. Graham-Lorence, S., and Peterson, J. A. (1996) FASEB J. 10, 206-214
6. Waller, C. L., Evans M. V., and McKinney, J. D. (1996) Drug Metab. Dispos. 2, 203-210
7. He, Y. Q., Szklarz, G. D., and Halpert, J. R. (1996) Arch. Biochem. Biophys. 335, 152-160
8. Strobel, S. M., and Halpert, J. R. (1997) Biochemistry 36, 11697-11706
9. Negishi, M., Uno, T., Honkakoski, P., Sueyoshi, T., Darden, T., and Pedersen, L. P. (1996) Biochimie (Paris) 78, 685-694
10. Goldstein, J. A., and de Morais, S. M. (1994) Pharmacogenetics 4, 285-299
11. Hoch, U., Falck, J. R., and Ortiz de Montellano, P. R. (2000) J. Biol. Chem. 275, 26952-26958
12. Domanski, T. L., Schultz, K. M., Roussel, F., Stevens, J. C., and Halpert, J. R. (1999) J. Pharmacol. Exp. Ther. 290, 1141-1147
13. He, Y. Q., Harlow, G. R., Szklarz, G. D., and Halpert, J. R. (1998) Arch. Biochem. Biophys. 350, 333-339
14. Ibeanu, G. C., Ghanayem, B. I., Linko, P., Li, L., Pederson, L. G., and Goldstein, J. A. (1996) J. Biol. Chem. 271, 12496-12501
15. Pikuleva, I., Puchkaev, A., and Bjorkhem, I. (2001) Biochemistry 40, 7621-7629
16. Nakayama, K., Puchkaev, A., and Pikuleva, I. (2001) J. Biol. Chem. 276, 31459-31465
17. Tsao, C. C., Wester, M. R., Ghanayem, B., Coulter, S. J., Chanas, B., Johnson, E. F., and Goldstein, J. A. (2001) Biochemistry 40, 1937-1944
18. Poulos, T. L., Cupp-Vickery, J., and Li, H. (1995) in Cytochrome P450: Structure, Mechanism, and Biochemistry (Ortiz de Montellano, P. R., ed) pp. 125-150, Plenum Press, New York
19. Poulos, T. L., Finzel, B. C., Gunsalus, I. C., Wagner, G. C., and Kraut, J. (1985) J. Biol. Chem. 260, 16122-16130
20. Podust, L. M., Poulos, T. L., and Waterman, M. R. (2001) Proc. Natl. Acad. Sci. U. S. A. 98, 3068-3073
21. Luo, Z., He, Y. A., and Halpert, J. R. (1994) Arch. Biochem. Biophys. 309, 52-57
22. Spatzenegger, M., Liu, H., Wang, Q., Debarber, A., Koop, D. R., and Halpert, J. R. (2003) J. Pharmacol. Exp. Ther. 304, 477-487
23. Afzelius, L., Zamora, I., Ridderström, M., Andersson, T. B., Karlén, A., and Masimirembwa, C. M. (2001) Mol. Pharmacol. 59, 909-919
24. Spatzenegger, M., Wang, Q., He, Y. Q., Wester, M. R., Johnson, E. F., and Halpert, J. R. (2001) Mol. Pharmacol. 59, 475-484
25. Lewis, D. F. V. (2002) J. Inorg. Biochem. 91, 502-514
26. Cosme, J., and Johnson, E. F. (2000) J. Biol. Chem. 275, 2545-2553
27. Kedzie, K. M., Balfour, C. A., Escobar, G. Y., Grimm, S. W., He, Y. A., Pepperl, D. J., Regan, J. W., Stevens, J. C., and Halpert, J. R. (1991) J. Biol. Chem. 266, 22515-22521
28. Halpert, J. R., and He, Y. A. (1993) J. Biol. Chem. 268, 4453-4457
29. He, Y. A., Luo, Z., Klekotka, P. A., Burnett, V. L., and Halpert, J. R. (1994) Biochemistry 33, 4419-4424
30. Szklarz, G. D., He, Y. A., and Halpert, J. R. (1995) Biochemistry 34, 14312-14322
31. Kobayashi, Y., Strobel, S. M., Hopkins, N. E., Alworth, W. L., and Halpert, J. R. (1998) Drug Metab. Dispos. 26, 1026-1030
32. Domanski, T. L., He, Y. Q., Scott, E. E., Wang, Q., and Halpert, J. R. (2001) Arch. Biochem. Biophys. 394, 21-28
33. Scott, E. E., Spatzenegger, M., and Halpert, J. R. (2001) Arch. Biochem. Biophys. 395, 57-68
34. Harlow, G. R., He, Y. A., and Halpert, J. R. (1997) Biochim. Biophys. Acta 1338, 259-266
35. Omura, T., and Sato, R. (1964) J. Biol. Chem. 239, 2379-2387
36. Ciaccio, P. J., and Halpert, J. R. (1989) Arch. Biochem. Biophys. 271, 284-299
37. Paulsen, M. D., and Ornstein, R. L. (1991) Proteins 11, 184-204
38. Paulsen, M. D., and Ornstein, R. L. (1992) J. Comput. Aided Mol. Des. 6, 449-460
39. Scott, E. E., He, Y. Q., and Halpert, J. R. (2002) Chem. Res. Toxicol. 15, 1407-1413
40. Lindberg, R. L., and Negishi, M. (1989) Nature 339, 632-634
41. Uno, T., Mitchell, E., Aida, K., Lambert, M. H., Darden, T. A., Pedersen, L. G., and Negishi, M. (1997) Biochemistry 36, 3193-3198
42. Negishi, M., Uno, T., Darden, T. A., Sueyoshi, T., and Pedersen, L. G. (1996) FASEB J. 10, 683-689
43. Parikh, A., Josephy, P. D., and Guengerich, F. P. (1999) Biochemistry 38, 5283-5289
44. Juvonen, R. O., Iwasaki, M., and Negishi, M. (1991) J. Biol. Chem. 266, 16431-16435
45. Miles, C. S., Ost, T. W. B., Noble, M. A., Munro, A. W., and Chapman, S. K. (2000) Biochim. Biophys. Acta 1543, 383-407
46. Farinas, E. T., Bulter, T., and Arnold, F. H. (2001) Curr. Opin. Biotechnol. 12, 545-551
47. Cirino, P. C., and Arnold, F. H. (2002) Curr. Opin. Chem. Biol. 6, 130-135