Interaction between substrate and oxygen ligand responsible for effective O-O bond cleavage in bovine cytochrome P450 steroid 21-hydroxylase proved by Raman spectroscopy

Journal of Biological Chemistry

Volumn 283, Issue 7, 2008, Pages 3708-3717

  Tosha, Takehiko ^a,d   Kagawa, Norio ^b   Arase, Miharu ^b   Waterman, Michael R ^c   Kitagawa, Teizo ^a  

^a OKAZAKI INSTITUTE FOR INTEGRATIVE BIOSCIENCE   (Japan)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c TOYOTA PHYSICAL AND CHEMICAL RESEARCH INSTITUTE   (Japan)

^d SAARLAND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING SITES; CHEMICAL REACTIONS; COMPLEXATION; HYDROGEN; HYDROGEN BONDS; HYDROXYLATION; LIGANDS; MODULATION; NONMETALS; OXYGEN;

BOND CLEAVAGES; BOND SCISSIONS; BOVINE CYTOCHROMES; DIFFERENT SUBSTRATES; FUNCTIONAL PROPERTIES; HYDROXYL GROUPS; HYDROXYLASE; HYDROXYLATION REACTIONS; ONE FORMS; OXYGEN COMPLEXES; OXYGEN LIGANDS; STRETCHING MODES; TERMINAL OXYGEN ATOMS; THIOLATE;

SUBSTRATES;

HEME; HYDROGEN PEROXIDE; HYDROXYPROGESTERONE; OXYGEN; PROGESTERONE; STEROID 21 MONOOXYGENASE; LIGAND;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; COW; EXCITATION; HYDROGEN BOND; HYDROXYLATION; NONHUMAN; OXYGEN AFFINITY; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAMAN SPECTROMETRY; STRUCTURE ANALYSIS; ANIMAL; CATTLE; ENZYME SPECIFICITY; HYDROLYSIS; METABOLISM; METHODOLOGY;

BOVINAE;

ANIMALS; CATTLE; HYDROGEN PEROXIDE; HYDROLYSIS; LIGANDS; OXYGEN; SPECTRUM ANALYSIS, RAMAN; STEROID 21-HYDROXYLASE; SUBSTRATE SPECIFICITY;

EID: 42949155921     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M707338200     Document Type: Article

References (64)

1. Kagawa, N., and Waterman, M. R. (1991) J. Biol. Chem. 266, 11199-11204
2. Kagawa, N., and Waterman, M. R. (1990) J. Biol. Chem. 265, 11299-11305
3. White, P. C., and Speiser, P. W. (2000) Endocr. Rev. 21, 245-291
4. White, P. C., New, M. I., and Dupont, B. (1984) Proc. Natl. Acad. Sci. U. S. A. 81, 7505-7509
5. Higashi, Y., Yoshioka, H., Yamane, M., Gotoh, O., and Fujii-Kuriyama, Y. (1986) Proc. Natl. Acad. Sci. U. S. A. 83, 2841-2845
6. Kominami, S., Ochi, H., Kobayashi, Y., and Takemori, S. (1980) J. Biol. Chem. 255, 3386-3394
7. Higuchi, A., Kominami, S., and Takemori, S. (1991) Biochim. Biophys. Acta 1084, 240-246
8. Kominami, S., Owaki, A., Iwanaga, T., Tagashira-Ikushiro, H., and Yamazaki, T. (2001) J. Biol. Chem. 276, 10753-10758
9. Estabrook, R. W., Cooper, D. Y., and Rosenthal, O. (1963) Biochem. Z. 338, 741-755
10. Arase, M., Waterman, M. R., and Kagawa, N. (2006) Biochem. Biophys. Res. Commun. 344, 400-405
11. Kagawa, N., Cao, Q., and Kusano, K. (2003) Steroids 68, 205-209
12. Kagawa, N., Hori, H., Waterman, M. R., and Yoshioka, S. (2004) Steroids 69, 235-243
13. Tosha, T., Kagawa, N., Ohta, T., Yoshioka, S., Waterman, M. R., and Kitagawa, T. (2006) Biochemistry 45, 5631-5640
14. Nickerson, D. P., Harford-Cross, C. F., Fulcher, S. R., and Wong, L. L. (1997) FEBS Lett. 405, 153-156
15. Kadkhodayan, S., Coulter, E. D., Maryniak, D. M., Bryson, T. A., and Dawson, J. H. (1995) J. Biol. Chem. 270, 28042-28048
16. Yoshioka, S., Takahashi, S., Ishimori, K., and Morishima, I. (2000) J. Inorg. Biochem. 81, 141-151
17. Yoshioka, S., Tosha, T., Takahashi, S., Ishimori, K., Hori, H., and Morishima, I. (2002) J. Am. Chem. Soc. 124, 14571-14579
18. Uchida, T., and Kitagawa, T. (2005) Acc. Chem. Res. 38, 662-670
19. Rousseau, D. L., Li, D., Couture, M., and Yeh, S. R. (2005) J. Inorg. Biochem. 99, 306-323
20. Smulevich, G., Feis, A., and Howes, B. D. (2005) Acc. Chem. Res. 38, 433-440
21. Peterson, J. A., Ishimura, Y., and Griffin, B. W. (1972) Arch. Biochem. Biophys. 149, 197-208
22. Jameson, G. N., Jin, W., Krebs, C., Perreira, A. S., Tavares, P., Liu, X., Theil, E. C., and Huynh, B. H. (2002) Biochemistry 41, 13435-13443
23. Ortiz de Montellano, P. R. (2005) Cytochrome P450: Structure, Mechanism, and Biochemistry, 3rd Ed., Plenum Publishing Corp., New York
24. Abe, M., Kitagawa, T., and Kyogoku, Y. (1978) J. Chem. Phys. 69, 4526-4534
25. Spiro, T. G., and Li, X.-Y. (1988) in Biological Applications of Raman Spectroscopy (Spiro, T. G., ed) Vol. 3, pp. 1-37, John Wiley & Sons, Inc., New York
26. Wells, A. V., Li, P., Champion, P. M., Martinis, S. A., and Sligar, S. G. (1992) Biochemistry 31, 4384-4393
27. Chen, Z., Ost, T. W., and Schelvis, J. P. (2004) Biochemistry 43, 1798-1808
28. Hu, S., Morris, I. K., Singh, J. P., Smith, K. M., and Spiro, T. G. (1993) J. Am. Chem. Soc. 115, 12446-12458
29. Hu, S., Smith, K. M., and Spiro, T. G. (1996) J. Am. Chem. Soc. 118, 12638-12646
30. Neri, F., Indiani, C., Baldi, B., Vind, J., Welinder, K. G., and Smulevich, G. (1999) Biochemistry 38, 7819-7827
31. Peterson, E. S., Friedman, J. M., Chien, E. Y., and Sligar, S. G. (1998) Biochemistry 37, 12301-12319
32. Hildebrand, D. P., Burk, D. L., Maurus, R., Ferrer, J. C., Brayer, G. D., and Mauk, A. G. (1995) Biochemistry 34, 1997-2005
33. Champion, P. M., Stallard, B. R., Wagner, G. C., and Gunsalus, I. C. (1982) J. Am. Chem. Soc. 104, 5469-5472
34. Bangcharoenpaurpong, O., Champion, P. M., Hall, K. S., and Hager, L. P. (1986) Biochemistry 25, 2374-2378
35. Chen, Z., Wang, L. H., and Schelvis, J. P. (2003) Biochemistry 42, 2542-2551
36. Schelvis, J. P., Berka, V., Babcock, G. T., and Tsai, A. L. (2002) Biochemistry 41, 5695-5701
37. Santolini, J., Roman, M., Stuehr, D. J., and Mattioli, T. A. (2006) Biochemistry 45, 1480-1489
38. Ozaki, Y., Kitagawa, T., Kyogoku, Y., Imai, Y., Hashimoto-Yutsudo, C., and Sato, R. (1978) Biochemistry 17, 5826-5831
39. Sligar, S. G., and Gunsalus, I. C. (1976) Proc. Natl. Acad. Sci. U. S. A. 73, 1078-1082
40. Modi, S., Sutcliffe, M. J., Primrose, W. U., Lian, L. Y., and Roberts, G. C. (1996) Nat. Struct. Biol. 3, 414-417
41. Chartier, F. J., and Couture, M. (2007) J. Biol. Chem. 282, 20877-20886
42. Li, D., Kabir, M., Stuehr, D. J., Rousseau, D. L., and Yeh, S. R. (2007) J. Am. Chem. Soc. 129, 6943-6951
43. Ledbetter, A. P., McMillan, K., Roman, L. J., Masters, B. S., Dawson, J. H., and Sono, M. (1999) Biochemistry 38, 8014-8021
44. Bec, N., Gorren, A. C., Voelker, C., Mayer, B., and Lange, R. (1998) J. Biol. Chem. 273, 13502-13508
45. Hu, S., Schneider, A. J., and Kincaid, J. R. (1991) J. Am. Chem. Soc. 113, 4815-4822
46. Chartier, F. J., Blais, S. P., and Couture, M. (2006) J. Biol. Chem. 281, 9953-9962
47. Couture, M., Stuehr, D. J., and Rousseau, D. L. (2000) J. Biol. Chem. 275, 3201-3205
48. Sjodin, T., Christian, J. F., Macdonald, I. D., Davydov, R., Unno, M., Sligar, S. G., Hoffman, B. M., and Champion, P. M. (2001) Biochemistry 40, 6852-6859
49. Bangcharoenpaurpong, O., Rizos, A. K., Champion, P. M., Jollie, D., and Sligar, S. G. (1986) J. Biol. Chem. 261, 8089-8092
50. Macdonald, I. D. G., Sligar, S. G., Christian, J. F., Unno, M., and Champion, P. M. (1999) J. Am. Chem. Soc. 121, 376-380
51. Lu, C., Egawa, T., Wainwright, L. M., Poole, R. K., and Yeh, S. R. (2007) J. Biol. Chem. 282, 13627-13636
52. Yoshimura, H., Yoshioka, S., Kobayashi, K., Ohta, T., Uchida, T., Kubo, M., Kitagawa, T., and Aono, S. (2006) Biochemistry 45, 8301-8307
53. Ohta, T., Yoshimura, H., Yoshioka, S., Aono, S., and Kitagawa, T. (2004) J. Am. Chem. Soc. 126, 15000-15001
54. Yeh, S. R., Couture, M., Ouellet, Y., Guertin, M., and Rousseau, D. L. (2000) J. Biol. Chem. 275, 1679-1684
55. Nagano, S., Cupp-Vickery, J. R., and Poulos, T. L. (2005) J. Biol. Chem. 280, 22102-22107
56. Schlichting, I., Berendzen, J., Chu, K., Stock, A. M., Maves, S. A., Benson, D. E., Sweet, R. M., Ringe, D., Petsko, G. A., and Sligar, S. G. (2000) Science 287, 1615-1622
57. Nagano, S., and Poulos, T. L. (2005) J. Biol. Chem. 280, 31659-31663
58. Imai, M., Shimada, H., Watanabe, Y., Matsushima-Hibiya, Y., Makino, R., Koga, H., Horiuchi, T., and Ishimura, Y. (1989) Proc. Natl. Acad. Sci. U. S. A. 86, 7823-7827
59. Vogel, K. M., Kozlowski, P. M., Zgierski, M. Z., and Spiro, T. G. (1999) J. Am. Chem. Soc. 121, 9915-9921
60. Das, T. K., Couture, M., Ouellet, Y., Guertin, M., and Rousseau, D. L. (2001) Proc. Natl. Acad. Sci. U. S. A. 98, 479-484
61. Wei, C. C., Wang, Z. Q., Hemann, C., Hille, R., and Stuehr, D. J. (2003) J. Biol. Chem. 278, 46668-46673
62. Tosha, T., Yoshioka, S., Ishimori, K., and Morishima, I. (2004) J. Biol. Chem. 279, 42836-42843
63. Nagano, S., Shimada, H., Tarumi, A., Hishiki, T., Kimata-Ariga, Y., Egawa, T., Suematsu, M., Park, S. Y., Adachi, S., Shiro, Y., and Ishimura, Y. (2003) Biochemistry 42, 14507-14514
64. Champion, P. M., Gunsalus, I. C., and Wagner, G. C. (1978) J. Am. Chem. Soc. 100, 3743-3751