A New Active Intermediate in Monooxygenations Catalyzed by Iron Porphyrin Complexes

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 6, 1998, Pages 1343-1353

  Murakami, Tatsuya ^a   Yamaguchi, Kazuya ^a,c   Watanabe, Yoshihito ^b   Morishima, Isao ^a  

^a KYOTO UNIVERSITY   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^c OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000916377     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.1343     Document Type: Article

References (58)

1. J. T. Groves, R. C. Haushalter, M. Nakamura, T. E. Nemo, and B. J. Evans, J. Am. Chem. Soc., 103, 2884 (1981).
2. a) J. T. Groves and Y. Watanabe, J. Am. Chem. Soc., 108, 7836 (1986);
3. b) J. T. Groves and Y. Watanabe, J. Am. Chem. Soc., 110, 8443 (1988);
4. c) Y. Mizutani, Y. Watanabe, and T. Kitagawa, J. Am. Chem. Soc., 116, 3439 (1994).
5. a) H. Tsurumaki, Y. Watanabe, and I. Morishima, J. Am. Chem. Soc., 115, 11784 (1993);
6. b) Y. Watanabe, K. Takehira, M. Shimizu, T. Hayakawa, H. Orita, and M. Kaise, J. Chem. Soc., Chem. Commun., 1990, 1262.
7. a) D. Dolphin, A. Forman, D. C. Borg, J. Fajar, and R. H. Felton, Proc. Natl. Acad. Sci. U.S.A., 68, 641 (1971);
8. b) T. G. Traylor, W. A. Lee, and D. V. Stynes, J. Am. Chem. Soc., 106, 755 (1984);
9. c) C. E. Schulz, R. Rutter, J. T. Sage, P. G. Debrunner, and L. P. Hager, Biochemistry, 23, 4743 (1984);
10. d) G. N. La Mar and J. S. de Roppe, J. Am. Chem. Soc., 102, 395 (1980);
11. e) G. N. La Mar, J. S. De Roppe, K. M. Smith, and K. C. Langry, J. Biol. Chem., 256, 237 (1981);
12. f) J. E. Roberts, B. M. Huffman, R. Rutter, and L. P. Hager, J. Biol. Chem., 256, 2118 (1981);
13. g) J. E. Roberts, B. M. Hoffman, R. Rutter, and L. P. Hager, J. Am. Chem. Soc., 103, 7654 (1981);
14. h) W. R. Patterson, T. L. Poulos, and D. B. Goodin, Biochemistry, 34, 4342 (1995);
15. i) R. Makino, T. Uno, Y. Nishimura, T. Iizuka, M. Tsuboi, and Y. Ishimura, J. Biol. Chem., 261, 8376 (1986).
16. a) A. Robert, B. Look, M. Momenteau, and B. Meunier, Inorg. Chem., 30, 796 (1991);
17. b) W.-J. Chuang and H. E. Van Wart, J. Biol. Chem., 267, 13293 (1992);
18. c) D. Mansuy, M. Lange, and J. C. Chottard, J. Am. Chem. Soc., 101, 6437 (1979).
19. D. Dolphin and R. H. Felton, Acc. Chem. Res., 7, 26 (1974).
20. C. E. Schultz, P. W. Devaney, H. Winkler, P. G. Debrunner, N. Doan, R. Chiang, R. Rutter, and L. P. Hager, FEBS Lett., 103, 102 (1979).
21. a) I. Morishima, Y. Takamuki, and Y. Shiro, J. Am. Chem. Soc., 106, 7666 (1984);
22. b) G. N. La Mar, V. Thanabal, R. D. Johnson, K. M. Smith, and D. W. Parish, J. Biol. Chem., 264, 5428 (1989).
23. a) K.-J. Paeng and J. R. Kincaid, J. Am. Chem. Soc., 110, 7915 (1988);
24. b) S. Hashimoto, Y. Mizutani, Y. Tatsuno, and T. Kitagawa, J. Am. Chem. Soc., 113, 6542 (1991).
25. T. H. Moss, A. Ehrenberg, and A. J. Bearden, Biochemistry, 8, 4159 (1969).
26. a) R. Makino and Y. Ishimura, Taisha, 19, 27 (1982);
27. b) P. R. Ortiz de Montellano, in "Cytochrome P-450," ed by P. R. Ortiz de Montellano, Plenum Press, New York (1986), p. 217;
28. c) Y. Watanabe, Shokubai, 32, 294 (1990);
29. d) E. J. Mueller, P. L. Loida, and S. G. Sugar, in "Cytochrome P-450," 2nd ed, ed by P. R. Ortiz de Montellano, Plenum Press, New York (1995), p. 83.
30. For example: a) Y. Watanabe and J. T. Groves, in "The Enzymes," ed by P. D. Boyer and D. S. Sigman, Academic Press, New York (1992), Vol. 20, pp. 405-452; b) B. Meunuier, Chem. Rev., 92, 1411 (1992).
31. For example: a) Y. Watanabe and J. T. Groves, in "The Enzymes," ed by P. D. Boyer and D. S. Sigman, Academic Press, New York (1992), Vol. 20, pp. 405-452; b) B. Meunuier, Chem. Rev., 92, 1411 (1992).
32. T. Egawa, H. Shimada, and Y. Ishimura, Biochem. Biophys. Res. Commun., 201, 1464 (1994).
33. P. M. Champion, J. Am. Chem. Soc., 111, 3433 (1989).
34. K. Yamaguchi, Y. Watanabe, and I. Morishima, J. Chem. Soc., Chem. Commun., 1992, 1721.
35. K. Jayaraj, J. Terner, A. Gold, D. A. Roberts, R. N. Austin, D. Mandon, R. Weiss, E. Bill, M. Müther, and A. X. Trautwein, Inorg. Chem., 35, 1632 (1996).
36. J. S. Lindsey and R. W. Wagner, J. Org. Chem., 54, 828 (1989).
37. J. Fajer, D. Borg, A. Forman, D. Dolphin, and R. H. Felton, J. Am. Chem. Soc., 92, 3451 (1970).
38. Z. Gross and L. Kaustov, Tetrahedron Lett., 36, 3735 (1995).
39. H. Kobayashi, T. Higuchi, Y. Kaizu, H. Osada, and M. Aoki, Bull. Chem. Soc. Jpn., 48, 3137 (1975).
40. C. A. Reed, T. Mashiko, S. P. Bentley, M. E. Kastner, W. R. Scheldt, K. Spartalian, and G. Lang, J. Am. Chem. Soc., 101, 2948 (1979).
41. M. Schmeisser, K. Dahmen, and P. Satori, Chem. Ber., 100, 1633 (1967).
42. a) N. N. Schwartz and J. H. Blumbergs, J. Org. Chem., 29, 1976 (1964);
43. b) L. S. Silbert, E. Siegel, and D. Swern, J. Org. Chem., 27, 1336 (1962).
44. H. Fujii, J. Am. Chem. Soc., 115, 4641 (1993).
45. A. Gold, K. Jayaraj, P. Doppelt, R. Weiss, G. Chottard, E. Bill, X. Ding, and A. X. Trautwein, J. Am. Chem. Soc., 110, 5756 (1988).
46. K. Yamaguchi, Y. Watanabe, and I. Morishima, J. Am. Chem. Soc., 115, 4058 (1993).
47. D. F. Evans, J. Chem. Soc., 1959, 2003.
48. a) A. Gold, K. Jayaraj, P. Doppelt, R. Weiss, E. Bill, X-Q. Ding, E. L. Bominaar, A. X. Trautwein, and H. Winkler, New J. Chem., 13, 169 (1989);
49. b) A. L. Balch, L. Latos-Grazynski, and M. W. Renner, J. Am. Chem. Soc., 107, 2983 (1985).
50. a) G. N. La Mar, in "NMR of Paramagnetic Molecules," ed by G. N. La Mar, W. D. Horrocks, and R. H. Holm, Academic Press, New York (1973), pp. 85-126;
51. b) G. N. La Mar and A. Walker, in "The Porphyrins," ed by D. Dolphin, Academic Press, New York (1978), Vol. 4, pp. 61-157.
52. 4 in this solution.
53. Z. Gross and S. Nimri, Inorg. Chem., 33, 1731 (1994).
54. a) J. P. Collman, T. Kodadek, S. A. Raybuck, J. I. Brauman, and I. M. Papazian, J. Am. Chem. Soc., 107, 4343 (1985);
55. b) J. T. Groves and Y. Watanabe, J. Am. Chem. Soc., 108, 507 (1986);
56. c) D. Ostovic and T. C. Bruice, Acc. Chem. Rev., 25, 314 (1992).
57. S. Ozawa, Y. Watanabe, and I. Morishima, J. Am. Chem. Soc., 116, 5832 (1994).
58. K. Machii, Y. Watanabe, and I. Morishima, J. Am. Chem. Soc., 117, 6691 (1995).