A Biomimetic Study of Cytochrome P450 Related Oxidations of Toluenes Using Synthetic Hemin

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 12, 1996, Pages 3513-3521

  Nakano, Taku ^a   Agatsuma, Noriko ^a   Kodama, Shiori ^a   Kakuda, Hiroko ^a   Dolphin, David ^b  

^a UNIVERSITY OF TOYAMA   (Japan)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000720580     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.3513     Document Type: Article

References (72)

1. a) T. L. Poulos and R. Raag, FASEB J., 6, 674 (1992)
2. b) F. P. Guengerich and T. L. Macdonald, Acc. Chem. Res., 17, 7 (1984).
3. a) P. L. Feldman, O. W. Griffith, and D. J. Steuhr, Chem. Eng. News, 71(51), 26 (1993)
4. b) I. Sakuma, D. J. Steuhr, S. S. Gross, C. Nathan, and R. Levi, Proc. Natl. Acad. Sci. U.S.A., 85, 8664 (1988).
5. a) T. L. Poulos, B. C. Finzel, I. C. Gunsalus, G. C. Wagner, and J. Kraut, J. Biol. Chem., 260, 16122 (1985)
6. b) K. G. Ravichandran, S. S. Boddupalli, C. A. Hasemann, J. A. Peterson, and J. Deisenhofer, Science, 261, 731 (1993).
7. a) T. J. McMurry and J. T. Groves, "Cytochrome p-450," ed by Ortiz de Montellano, Plenum, N. Y. (1986), p.1
8. b) J. T. Groves and T. E. Nemo, J. Am. Chem. Soc., 105, 5786 (1983)
9. c) A. J. Castellino and T. C. Bruice, J. Am. Chem. Soc., 110, 158 (1988).
10. a) J. T. Groves, R. C. Haushalter, M. Nakamura, T. E. Nemo, and B. J. Evans, J. Am. Chem. Soc., 103, 2884 (1981)
11. b) H. Fujii, J. Am. Chem. Soc., 115, 4641 (1993)
12. c) K. Jayaraj, J. Terner, A. Gold, D. A. Goberts, R. N. Austin, D. Mandon, R. Weiss, E. Bil, M. Muther, and A. X. Trautwein, Inorg. Chem., 35, 1632 (1996).
13. a) J. T. Groves, G. A. Mcheky, R. E. White, and M. J. Coon, Biochem. Biophys. Res. Commun., 81 154 (1978)
14. b) D. Mansuy, J.-F. Batoli, and M. Momenteau, Tetrahedron Lett., 23, 2781 (1982)
15. c) T. G. Traylor, K. W. Hill, W.-P. Fann, S. Tuchiya, and B. E. Danlap, J. Am. Chem. Soc., 114, 1308 (1992).
16. T. G. Traylor and J. P. Ciccone, J. Am. Chem. Soc., 111, 8413 (1989).
17. J. R. Lindsay Smith, P. N. Balasubramanian, and T. C. Bruice, J. Am. Chem. Soc., 111, 1477 (1989).
18. J. T. Groves and R. S. Myers, J. Am. Chem. Soc., 105, 5791 (1983).
19. 8Cl is rapidly destroyed in the presence of PFIB but is much more stable in the presence of iodosylbenzene.
20. T. G. Traylor, T. Nakano, B. E. Dunlap, P. S. Traylor, and D. Dolphin, J. Am. Chem. Soc., 108, 2782 (1986); T. G. Traylor and A. R. Miksztal, J. Am. Chem. Soc., 111, 7443 (1989).
21. T. G. Traylor, T. Nakano, B. E. Dunlap, P. S. Traylor, and D. Dolphin, J. Am. Chem. Soc., 108, 2782 (1986); T. G. Traylor and A. R. Miksztal, J. Am. Chem. Soc., 111, 7443 (1989).
22. a) P. S. Traylor, D. Dolphin, and T. G. Traylor, J. Chem. Soc., Chem. Commun., 1984, 279
23. b) T. G. Traylor, W.-P. Fann, and D. Bandyopadhyay, J. Am. Chem. Soc., 111, 8009 (1989).
24. a) T. Mashiko, D. Dolphin, T. Nakano, and T. G. Traylor, J. Am. Chem. Soc., 107, 3735 (1985)
25. b) J. P. Collman, P. D. Hampton, and J. I. Brauman, J. Am. Chem. Soc., 112, 2986 (1990)
26. c) Z.-Q. Tian, J. L. Richards, and T. G. Traylor, J. Am. Chem. Soc., 117, 21 (1995).
27. a) D. E. Chapman, T. J. Moore, S. R. Michener, and G. Powis, Drug Metab. Dispos., 18, 929 (1990)
28. b) K. T. Blanchard and J. B. Morris, Toxicol. Lett., 70, 253 (1994)
29. c) I. Gut, Y.Terelius, E. Frantik, I. Linhart, P. Soucek, B. Filipcova, and H. Kluckova, Arch. Toxicol., 67, 237 (1994).
30. a) K. Pyykko, Biochim. Biophys. Acta, 633, 1 (1980)
31. b) K. Pyykko, Chem. Biol. Interact., 44, 299 (1983)
32. c) W. L. Backes, D. J. Sequeira, G. F. Cawley, and C. S. Eyer, Xenobiotica, 23, 1353 (1994)
33. d) R. Toftgard, T. Haaparanta, and J. Halpert, Toxicology, 39, 225 (1986)
34. e) R. E. White and M. B. McCarthy, Arch. Biochem. Biophys., 246, 19 (1986).
35. J. W. Daly, D. M. Jerna, and B. Witkop, Experientia, 28, 1129 (1972).
36. 8 was 16%.
37. H. Kobayashi, T. Higuchi, Y. Kaizu, H. Osada, and M. Aoki, Bull. Chem. Soc. Jpn., 48, 3137 (1975).
38. M. Schmeisser, K. Dahmen, and P. Sartori, Chem. Ber., 100, 1633 (1967).
39. T. G. Traylor, J. C. Marsters, Jr., T. Nakano, and B. E. Dunlap, J. Am. Chem. Soc., 107, 5537 (1985).
40. J. R. Lindsay Smith and P. R. Sleath, J. Chem. Soc., Perkin. Trans. 2, 1982, 1009.
41. P. Inchley, J.R. Lindsay Smith, and R. J. Lower, New J. Chem., 13, 669 (1989).
42. Without side chains, the hydroxylation of benzene was established using metal perhalogenated porphyrins. Cf. S. Tsuchiya and M. Seno, Chem. Lett., 1989, 263.
43. Benzene metabolisms were reported in rat and rabbit liver microsomes. Cf. a) I. Johansson and M. I-Sundberg, Cancer Res., 48, 5387 (1988);
44. b) R. P. Hanzlik, K. Hogberg, and C.M. Judson, Biochemistry, 23, 3048 (1984).
45. 2O.
46. O. Exner, in "Correlation Analysis in Chemistry: Recent Advances," ed by N. B. Chapman and J. Shorter, Plenum, New York (1978), pp. 439-540.
47. Y. Okamoto, T. Inukai, and H. C. Brown, J. Am. Chem. Soc., 80, 4969 (1958).
48. N. Colclough and J. R. Lindsay Smith, "The Activation of Dioxygen and Homogeneous Catalytic Oxidation," ed by D. H. R. Barton et al., Plenum Press, New York (1993), pp. 171-182.
49. J. M. Dust and D. R. Arnold, J. Am. Chem. Soc., 105, 1221 (1983).
50. L. M. Hjelemeland, L. Aronow, and J. R. Trudell, Biochem. Biophys. Res. Commun., 76, 541 (1977), and papers therein.
51. R. P. Hanzlik and K.-H. J. Ling, J. Org. Chem., 55, 3992 (1990).
52. H. L. Holland, F. M. Brown, B. Munoz, and R. W. Ninniss, J. Chem. Soc., Perkin. Trans. 2, 1988, 1557.
53. V. P. Miller, R. A. Tschirret-Guth, and P. R. Ortiz de Montellano, Arch. Biochem. Biophys., 319, 333 (1995).
54. R. P. Hanzlik, A. R. Schaefer, J. B. Moon, and C. M. Judson, J. Am. Chem. Soc., 109, 4926 (1987).
55. a) T. G. Traylor, W. B. Lee, and D. V. Stynes, J. Am. Chem. Soc., 106, 755 (1984)
56. b) T. G. Traylor, W. B. Lee, and D. V. Stynes, Tetrahedron, 40, 553 (1984)
57. c) W. A. Lee and T. C. Bruice, J. Am. Chem. Soc., 107, 513 (1985).
58. T. G. Traylor, Pure Appl. Chem., 63, 625 (1991), and papers therein.
59. a) J. T. Groves, G. A. McClusky, R. E. White, and M. J. Coon, Biochem. Biophys. Res. Commun., 81, 154 (1978)
60. b) R. E. White, J. T. Groves, and G. A. McClusky, Acta Biol. Med. Ger., 38, 475 (1979).
61. a) M. L. Bender and M. S. Feng, J. Am. Chem. Soc., 82, 6318 (1960)
62. b) J. M. Jones and M. L. Bender, J. Am. Chem. Soc., 82, 6322 (1960).
63. M. Newcomb, M.-H. Le Tadic-Biadatti, D. L. Chestney, E. S. Roberts, and P. F. Hollenberg, J. Am. Chem. Soc., 117, 12085 (1995).
64. a) P. R. Ortiz de Montellano and R. A. Stearns, J. Am. Chem. Soc., 109, 3415 (1987)
65. b) J. K. Atkinson, P. F. Hollenberg, K. U. Ingold, C. C. Johnson, M.-H. Le Tadic, M. Newcomb, and D. A. Putt, Biochemistry, 33, 10630 (1994)
66. c) M. Newcomb, M.-H. Le Tadic, D. A. Putt, and P. F. Hollenberg, J. Am. Chem. Soc., 117, 3312 (1995).
67. If the concerted mechanism is true, the activities of cumene indicated that normal side on approach is sterically hindered and the approach should be partially tilted.
68. a) D. J. Waxman and C. Walsh, Biochemistry, 22, 4846 (1983)
69. b) T. Nakajima, R.-S. Wang, E. Elovaara, S. S. Park, H. V. Gelboin, E. Hietanen, and H. Vainio, Biochem. Pharmacol., 41, 395 (1991)
70. c) R.-S. Wang and T. Nakajima, Arch. Toxicol., 65, 39 (1991).
71. a) M. Mori, T. Kawajiri, M. Sayama, T. Miyahara, and H. Kozuka, Xenobiotica, 19, 731 (1989)
72. b) M. Sayama, M. Inoue, M. Mori, Y Maruyama, and H. Kozuka, Xenobiotica, 22, 633 (1992).