Hydrogen-bonded dioxygen adduct of an iron porphyrin with an alkanethiolate ligand: An elaborate model of cytochrome P450

Angewandte Chemie - International Edition

Volumn 39, Issue 11, 2000, Pages 1989-1991

  Matsu Ura, Mikiya ^a   Tani, Fumito ^a   Nakayama, Shinya ^a   Nakamura, Nobuhumi ^a   Naruta, Yoshinori ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Dioxygen complexes; Hydrogen bonds; O O activation; Porphyrinoids; S ligands

Indexed keywords

CYTOCHROME P450; IRON; PORPHYRIN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; ORGANIC CHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034595641     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000602)39:11<1989::AID-ANIE1989>3.0.CO;2-T     Document Type: Article

References (35)

1. a) Y. Watanabe, J. T. Groves, Enzymes 1992, 20, 405;
2. b) P. Ortiz de Montellano. Cytochrome P-450. Structure, Mechanism, and Biochemistry, 2nd ed., Plenum Press, New York, 1995;
3. c) M. Sono, M. P. Roach, E. D. Coulter, J. H. Dawson, Chem. Rev. 1996, 96, 2841;
4. d) H. Shimada, S. G. Sligar, H. Xeom, Y. Ishimura in Oxygenase and Model Systems (Ed.: F. Funabiki), Kluwer Academic, Dordrechet, 1997, pp. 195-221, and references therein.
5. T. L. Poulos, B. C. Finzel, I. C. Gunsalus, G. C. Wagner, J. Kraut, J. Biol. Chem. 1984, 260, 16122.
6. a) M. Imai, H. Shimada, Y. Watanabe, Y. Matsushima-Hibiya, R. Makino, H. Koga, T. Horiguchi, Y. Ishimura, Proc. Natl. Acad. Sci. USA 1989, 86, 7823;
7. b) N. C. Gerber, S. G. Sliger, J. Am. Chem. Soc. 1992, 114, 8742;
8. c) M. Vidakovic, S. G. Sugar, H. Li, T. L. Poulos, Biochemistry 1998, 37, 9211.
9. a) J. H. Dawson, Science 1988, 240, 433;
10. b) T. L. Poulos, Adv. Inorg. Biochem. 1988, 7, 1.
11. For typical examples, see; a) H. Ogoshi, H. Sugimoto, Z. Yoshida, Tetrahedron Lett. 1975, 27, 2289;
12. b) J. P. Collman, S. E. Groh, J. Am. Chem. Soc. 1982, 104, 1391:
13. c) H. Patzelt, W.-D. Woggon, Helv. Chim. Acta. 1992, 75, 523;
14. d) T. Higuchi, S. Uzu, M. Hirobe, J. Am. Chem. Soc. 1990, 112, 7051;
15. e) N. Ueyama, N. Nishikawa, Y. Yamada, T. Okamura, A. Nakamura, J. Am. Chem. Soc. 1996, 118, 12826;
16. f) H. Volz, M. Holtzbecher, Angew. Chem. 1997, 109, 1510; Angew. Chem. Int. Ed. Engl. 1997, 36, 1442.
17. f) H. Volz, M. Holtzbecher, Angew. Chem. 1997, 109, 1510; Angew. Chem. Int. Ed. Engl. 1997, 36, 1442.
18. a) C. K. Chang, D. Dolphin, J. Am. Chem. Soc. 1976. 98, 1607;
19. b) M. Schappacher, L. Ricard, J. Fisher, R. Weiss, E. Bill, R. Montiel-Montoya, H. Winkler, A. X. Trautwein, Eur. J. Biochem. 1987, 168, 419;
20. c) D. El-Kasmi, C. Tetreau, D. Lavatte, M. Momenteau, J. Am. Chem. Soc. 1995, 117, 6041.
21. F. Tani, S. Nakayama, M. Ichimura, N. Nakamura, Y. Naruta, Chem. Lett. 1999, 729.
22. a) Y. Naruta, F. Tani, N. Ishihara, K. Maruyama, J. Am. Chem. Soc. 1991, 113, 6865;
23. b) Y. Naruta, F. Tani, K. Maruyama, Tetrahedron: Asymmetry 1991, 2, 533.
24. [8a] in which compound the positions of the binaphthalene bridges are different between the upper and lower sides of the heme plane is omitted in Scheme 1.
25. E. McCandlish, A. R. Miksztal, M. Nappa, A. Q. Sprenger, J. S. Valentine, J. D. Stong, T. G. Spiro, J. Am. Chem. Soc. 1980, 102, 4268.
26. a) S. Hu. A. J. Schneider, J. R. Kincaid, J. Am. Chem. Soc. 1991, 113, 4815;
27. b) T. Egawa, T. Ogura, R. Makino, Y. Ishimura, T. Kitagawa, J. Biol. Chem. 1991, 266, 10246;
28. c) I. D. G. Macdonald, S. G. Sligar, J. F. Christian, M. Unno, P. M. Champion, J. Am. Chem. Soc. 1999, 121, 376.
29. G. Chottard, M. Schapracher, L. Ricard, R. Weiss, Inorg. Chem. 1984, 23, 4557.
30. H. Brunner, Naturwissenschaften 1974, 61, 129.
31. M. Tsubaki, N.-T. Yu, Proc. Natl. Acad. Sci. USA 1981, 78, 3581.
32. T. Kitagawa, M. R. Ondrias, D. L. Rousseau, M. Ikeda-Saito, T. Yonetani, Nature 1982, 298, 869.
33. a) M. Momenteau, C.A. Reed, Chem. Rev. 1994, 94, 659;
34. b) G. B. Jameson, J. A. Ibers in Bioinorganic Chemistry (Eds.: I. Berlini, H. B. Gray, S. Lippard, J. Valentine), University Science Books, California, 1994, pp. 167-252, and references therein.
35. cam has been recently reported. I. Schlichting, J. Berendzen, K. Chu, A. M. Stock, S. A. Maves, D. E. Benson, R. M. Sweet, D. Ringe, G. A. Petsko, S. G. Sligar, Science 2000, 287, 1615.