Model systems for cytochrome P450 dependent mono-oxygenases. Part 1. Oxidation of alkenes and aromatic compounds by tetraphenylporphinatoiron(III) chloride and iodosylbenzene

Journal of the Chemical Society, Perkin Transactions 2

Volumn , Issue 8, 1982, Pages 1009-1015

  Lindsay Smith, John R ^a   Sleath, Paul R ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049111500     PISSN: 1472779X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (77)

1. D. M. Jerina, J. W. Daly, and B. Witkop, in ‘Biogenic Amines and Physiological Membranes in Drug Therapy, Part B,’ eds. J. H. Biel and L. G. Abood, Marcel Dekker, New York, 1971, p. 413.
2. V. Ullrich, Angew. Chem. Int. Ed., 1972, 11, 701.
3. G. A. Hamilton, in ‘Molecular Mechanisms of Oxygen Activation,’ ed. O. Hayaishi, Academic Press, New York, 1974, p. 405.
4. S. G. Sligar, K. A. Kennedy, and D. C. Pearson, Proc. Natl. Acad. Sci. U.S.A., 1980, 77, 1240.
5. M. J. Coon and R. E. White, in ‘Metal Ion Activation of Molecular Oxygen,’ ed. T. G. Spiro, Wiley, New York, 1980, p. 73.
6. J. T. Groves, S. Krishnan, G. E. Avaria, and T. E. Nemo, Adv. Chem. Ser., 1980, 191, 277.
7. D. C. Heinbrook and S. G. Sligar, Biochem. Biophys. Res. Commun., 1981, 99, 530.
8. J. W. Daly, D. M. Jerina, and B. Witkop, Experimentia, 1972, 28, 1129.
9. D. M. Jerina, Chem. Tech., 1973, 4, 120.
10. U. Frommer, V. Ullrich, and S. Orrenius, FEBS Lett., 1974, 41, 14.
11. J. T. Groves, G. A. McClusky, R. E. White, and M. J. Coon, Biochem. Biophys. Res. Commun., 1978, 81, 154.
12. R. E. White, J. T. Groves, and G. A. McClusky, Acta Biol. Med. Germ., 1979, 88, 475.
13. M. B. Dearden, C. R. E. Jefcoate, and J. R. Lindsay Smith, Adv. Chem. Ser., 1968, 77, 260.
14. L. Castle, J. R. Lindsay Smith, and G. V. Buxton, J. Mol. Catal., 1980, 7, 235.
15. M. A. Brook, L. Castle, J. R. Lindsay Smith, R. Higgins, and K. P. Morris, J. Chem. Soc., Perkin Trans. 2, in the press, and earlier papers in the series.
16. J. R. Lindsay Smith, R. E. Piggott, and P. R. Sleath, J. Chem. Soc., Chem. Commun., 1982, 55.
17. K. C. Leibman and E. Ortiz, J. Pharmacol. Exp. Therap., 1970, 173, 242.
18. E. W. Maynert, R. L. Foreman, and T. Watanabe, J. Biol. Chem., 1970, 245, 5234.
19. R. P. Hanzlik and G. O. Shearer, Biochem. Pharmacol., 1978, 27, 1441.
20. J. T. Groves, T. E. Nemo, and R. S. Myers, J. Am. Chem. Soc., 1979, 101, 1032.
21. F. Lichtenberger, W. Nastainczyk, and V. Ullrich, Biochem. Biophys. Res. Commun., 1976, 70, 939.
22. F. F. Kadlubar, K. C. Morton, and D. M. Ziegler, Biochem. Biophys. Res. Commun., 1973, 54, 1255.
23. A. D. Rahimtula and P. J. O’Brien, Biochem. Biophys. Res. Commun., 1974, 60, 440.
24. J. T. Groves, W. J. Kruper, T. E. Nemo, and R. S. Myers, J. Mol. Catal., 1980, 7, 169.
25. W. v. E. Doering and W. A. Henderson, J. Am. Chem. Soc., 1958, 80. 5274.
26. M. S. Kharasch and H. N. Friedlander, J. Org. Chem., 1949, 14, 239.
27. M. S. Kharasch and M. Sage, J. Org. Chem., p. 537.
28. J. E. Dubois and G. Mouvier, Tetrahedron Lett., 1963, 1325; 1965, 1629.
29. D. Swern, Chem. Rev., 1949, 45, 1.
30. B. M. Lynch and K. H. Pausacker, J. Chem. Soc., 1955, 1525.
31. Y. Ishii and Y. Inamato, Kogyo Kagaku Zasshi, 1960, 63, 765.
32. Y. Ogata and I. Tabushi, J. Am. Chem. Soc., 1961, 83, 3440.
33. G. R. Howe and R. R. Hiatt, J. Org. Chem., 1971, 36, 2493.
34. R. P. Hanzlik and G. O. Shearer, J. Am. Chem. Soc., 1975, 97, 5231.
35. R. E. Keay and G. A. Hamilton, J. Am. Chem. Soc., 1976, 98, 6578.
36. H.-S. Ryang and C. S. Foote, J. Am. Chem. Soc., 1980, 102, 2129.
37. R. G. Carlson, N. S. Behn, and C. Cowles, J. Org. Chem., 1971, 36, 3832.
38. E. D. Morris and H. Niki, J. Phys. Chem., 1971, 75, 3640.
39. R. Ruiz Diaz, K. Selby, and D. J. Waddington, J. Chem. Soc., Perkin Trans. 2, 1975, 758.
40. R. J. Cvetanović and R. S. Irwin, J. Chem. Phys., 1967, 46, 1694.
41. R. J. Cvetanović, Can. J. Chem., 1960, 38, 1678.
42. D. Swern, Org. Peroxides, 1971, 2, 355.
43. M. N. Sheng and J. G. Zajacek, Adv. Chem. Ser., 1968, 76, 418.
44. K. Ishikawa, H. C. Charles and G. W. Griffin, Tetra hedron Lett., 1977, 427.
45. S. Krishnan, D. G. Kuhn, and G. A. Hamilton, hedron Lett., p. 1369.
46. K. Ishikawa and G. W. Griffin, Angew. Chem. Int. Ed., 1977, 16, 171.
47. S. Goto, A. Hori, S. Takamuku, and H. Sakurai, Bull. Chem. Soc. Jpn., 1978, 51, 1569.
48. M. N. Akhtar, D. R. Boyd, J. D. Neill, and D. M- Jerina, J. Chem. Soc., Perkin Trans. 1, 1980, 1693.
49. B. L. Van Duuren, G. Witz, and S. Agarwal, J. Org. Chem., 1974, 39, 1032.
50. C. K. Chang and F. Ebina, J. Chem. Soc., Chem. Commun., 1981, 778.
51. D. R. Paulson, R. Ullman, R. B. Sloane, and G. L. Closs, J. Chem. Soc., Chem. Commun., 1974, 186.
52. Y. Ohkatsu and T. Tsuruta, Bull. Chem. Soc. Jpn., 1978, 51, 188.
53. C. L. Hill and B. C. Schardt, J. Am. Chem. Soc., 1980, 102, 6374.
54. J. T. Groves, W. J. Kruper, and R. C. Haushalter, J. Am. Chem. Soc., p. 6375.
55. T. Yamamoto and M. Kimura, J. Chem. Soc., Chem. Commun., 1977, 948.
56. D. M. Jerina, J. W. Daly, and B. Witkop, Biochem., 1971, 10, 366.
57. J. T. Groves, O. F. Akinbote, and G. E. Avaria, in ‘Micro- somes, Drug Oxidations and Chemical Carcinogenesis,’ eds. M. J. Coon, A. H. Conney, R. W. Estabrook, H. V. Gelboin, J. R. Gillette, and P. J. O’Brien, Academic Press, New York, 1980, p. 253.
58. T. L. Gilchrist and C. W. Rees, ‘Carbenes, Nitrenes, and Arynes,’ Nelson, London, 1969.
59. A. T. Pudzianowski and G. H. Loew, J. Am. Chem. Soc., 1980, 102, 5443.
60. E. L. Foreman and S. M. McElvain, J. Am. Chem. Soc., 1940, 62, 1435.
61. R. W. Strassburg, R. A. Gregg, and C. Walling, J. Am. Chem. Soc., 1947, 69, 2141.
62. B. Smith and R. Ohlson, Acta Chem. Scand., 1959, 13, 1253.
63. C. R. E. Jefcoate, J. R. Lindsay Smith, and R. O. C. Norman, J. Chem. Soc. B, 1969, 1013.
64. A. M. Jeffrey, H. J. C. Yeh, D. M. Jerina, T. R. Patel, J. F. Davey, and D. T. Gibson, Biochem., 1975, 14, 575.
65. T. Kutsuma, I. Nagayama, T. Okazaki, T. Sakamoto, and S. Akaboshi, Heterocycles, 1977, 8, 397.
66. R. B. Westkaemper and R. P. Hanzlik, Anal. Biochem., 1980, 102, 63.
67. M. Imuta and H. Ziffer, J. Org. Chem., 1979, 44, 1351.
68. C. C. Price and D. D. Carmelite, J. Am. Chem. Soc., 1966, 88, 4039.
69. R. M. Gerkin and B. Rickborn, J. Am. Chem. Soc., 1967, 89, 5850.
70. A. J. Lundeen and R. Van Hoozer, J. Org. Chem., 1967, 32, 3386.
71. A. T. Bottini, R. L. VanEtten, and A. J. Davidson, J. Am. Chem. Soc., 1965, 87, 755.
72. B. S. Furniss, A. J. Hannaford, V. Rogers, P. W. G. Smith, and A. R. Tatchell, ‘Vogel’s Textbook of Practical Organic Chemistry,’ Longmans, London, 1979, 4th edn., p. 921.
73. J. Biggs, N. B. Chapman, A. F. Finch, and V. Wray, J. Chem. Soc. B, 1971, 55.
74. C. O. Guss, J. Am. Chem. Soc., 1952, 74, 2561.
75. A. D. Alder, R. F. Longo, J. D. Finarelli, J. Goldmacher, J. Assour, and L. Korsakoff, J. Org. Chem., 1967, 32, 476.
76. P. Rothemund and A. R. Menotti, J. Am. Chem. Soc., 1948, 70, 1808.
77. H. J. Lucas, E. R. Kennedy, and M. W. Formo, Org. Synth., 1955, Coll. Vol. 3, 483.