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DOI: 10.1039/CS9972600355 (Review Article) Reference Section for: Chem. Soc. Rev., 1997, 26, 355-364

Molecular modelling of electron transfer systems by noncovalently linked porphyrin–acceptor pairing

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Takashi Hayashi and Hisanobu Ogoshi

Abstract

In the respiratory system, electron carriers such as ubiqui-none and cytochrome c play an important role in the electron transfer (ET) reaction between oxidoreductases embedded in the mitochondrial membrane. This review focuses on a strategy for constructing porphyrin–electron acceptor pairs via specific interactions and the evaluation of ET in these systems. Particularly, the molecular recognition of ubiqui-none analogues by porphyrin host molecules and the mimicking of protein–protein complexation using myoglobin reconstituted with a synthetic porphyrin are reviewed, and the characteristics of the photoinduced ET within noncovalently linked complexes are discussed.

References

  1. J. Deisenhofer, O. Epp, K. Miki, R. Huber and H. Michel, Nature, 1985, 318, 618 Search PubMed .
  2. M. R. Wasielewski, Chem. Rev., 1992, 92, 435 Search PubMed .
  3. H. Kurreck and M. Huber, Angew. Chem., Int. Ed. Engl., 1995, 34, 849 Search PubMed .
  4. J. L. Sessler, B. Wang, S. L. Springs and C. T. Brown, in Comprehensive Supramolecular Chemistry, Vol. 4, ed. Y. Murakami, Pergamon, Oxford, 1996, p. 311. Search PubMed .
  5. K. Sakamoto, H. Miyoshi, K. Takegami, T. Mogi, Y. Anraku and H. Lwamura, J. Biol. Chem., 1996, 271, 29897 Search PubMed .
  6. H. Pelletier and J. Kraut, Science, 1992, 258, 1748 Search PubMed .
  7. T. Tsukihara, H. Aoyama, E. Yamashita, T. Tomizaki, H. Yamaguchi, K. Shinzawa-Itoh, R. Nakashima, R. Yaono and S. Yoshikawa, Science Nature, 1995, 269, 1069 Search PubMed ; S. lwata, C. Ostermeier, B. Ludwig and H. Michel, Nature, 1995, 376, 660 Search PubMed .
  8. Y. Aoyama, M. Asakawa, Y. Matsui and H. Ogoshi, J. Am. Chem. Soc., 1991, 113, 6233 Search PubMed .
  9. (a) A. Harriman, Y. Kubo and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 388 Search PubMed ; (b) J. L. Sessler, B. Wang and A. Harriman, J. Am. Chem. Soc., 1993, 115, 10418 Search PubMed ; (c) A. Berman, E. S. Izraeli, H. Levanon and B. Wang, J. Am. Chem. Soc., 1995, 117, 8252 Search PubMed .
  10. Other models of non-covalently linked porphyrin-quinone systems: M. Gonzalez, A. McIntosh, J. Bolton and A. Weedon, J. Chem. Soc., Chem. Commun., 1984, 1138 Search PubMed ; Y. Kuroda, M. Ito, T. Sera and H. Ogoshi, J. Am. Chem. Soc., 1993, 115, 7003 Search PubMed ; H. Imahori, E. Yoshizawa, K. Yamada, K. Hagiwara, T. Okada and Y. Sakata, J. Chem. Soc., Chem. Commun., 1995, 1133 Search PubMed ; F. D'Souza, J. Am. Chem. Soc., 1996, 118, 923 Search PubMed ; C. A. Hunter and R. J. Shannon, Chem. Commun., 1996, 1361 Search PubMed .
  11. (a) T. Hayashi, T. Miyahara, N. Hashizume and H. Ogoshi, J. Am. Chem. Soc., 1993, 115, 2049 Search PubMed ; (b) T. Hayashi, T. Miyahara, Y. Aoyama, M. Kobayashi and H. Ogoshi, Pure Appl. Chem., 1994, 66, 797 Search PubMed ; (c) T. Hayashi, T. Miyahara, N. Koide, Y. Kato, H. Masuda and H. Ogoshi, J. Am. Chem. Soc., 1997, 119, 7281 Search PubMed .
  12. H. Ogoshi, Y. Kuroda, T. Mizutani and T. Hayashi, Pure Appl. Chem., 1996, 68, 1411 Search PubMed .
  13. (a) T. Hayashi, T. Miyahara, Y. Aoyama, M. Nonoguchi and H. Ogoshi, Chem. Lett., 1994, 1749 Search PubMed ; (b) T. Hayashi, T. Miyahara, S. Kumazaki, H. Ogoshi and K. Yoshihara, Angew. Chem. Int. Ed. Engl., 1996, 35, 1964 Search PubMed .
  14. H. Heitele, F. Pollinger, T. Häberle, M. E. Michel-Beyerle and H. A. Stab, J. Phys. Chem., 1984, 98, 7402 Search PubMed ; H. A. Staab, J. Weiser and E. Baumann, Chem. Ber., 1992, 125, 2275 Search PubMed .
  15. A. Harriman, D. Magda and J. L. Sessler, J. Phys. Chem., 1991, 95, 1530 Search PubMed .
  16. C. Turro, C. K. Chang, G. E. Leroi, R. I. Cukier and D. G. Nocera, J. Am. Chem. Soc., 1992, 114, 4013 Search PubMed .
  17. P. J. F. DeRege, S. A. Williams and M. J. Therein, Science, 1995, 269, 1409 Search PubMed .
  18. P. Bertrand, B. E. Bowler, J. Chang, B. M. Hoffman, H. B. Gray, A. Kuki, A. G. Mauk, G. McLendon, M. J. Natan, J. M. Nocek, A. L. Raphael, A. G. Sykes, M. J. Therein and S. A. Wallin, Structure and Bonding, vol. 25, Springer-Verlag, Berlin, 1991. Search PubMed .
  19. G. McLendon and R. Hake, Chem. Rev., 1992, 92, 481 Search PubMed ; J. M. Nocek, J. S. Zhou, S. D. Forest, S. Priyadarshy, D. N. Beratan, J. N. Onuchic and B. M. Hoffman, Chem. Rev., 1996, 96, 2459 Search PubMed ; M. M. Ivković-Jensen and N. M. Kostić, Biochemistry, 1996, 35, 15095 Search PubMed ; K. Wang, H. Mei, L. Geren, M. A. Miller, A. Saunders, X. Wang, J. L. Waldner, G. J. Pielak, B. Durham and F. Millett, Biochemistry, 1996, 35, 15107 Search PubMed .
  20. J. S. Zhou and M. A. J. Rodgers, J. Am. Chem. Soc., 1991, 113, 7728 Search PubMed .
  21. T. Hayashi, Y. Hitomi, A. Suzuki, T. Takimura and H. Ogoshi, Chem. Lett., 1995, 911 Search PubMed .
  22. T. Hayashi, T. Takimura, Y. Hitomi, T. Ohara, H. Ohara and H. Ogoshi, J. Chem. Soc., Chem. Commun., 1995, 545 Search PubMed ; T. Hayashi, T. Takimura, Y. Hitomi, T. Ohara, H. Ohara and H. Ogoshi, J. Chem. Soc., Chem. Commun., 1995, 2503 Search PubMed .
  23. T. Hayashi, T. Takimura and H. Ogoshi, J. Am. Chem. Soc., 1995, 117, 11606 Search PubMed .
  24. N. Mataga, A. Karen, T. Okada, S. Nishitani, N. Kurata, Y. Sakata and S. Misumi, J. Phys. Chem., 1984, 88, 5138 Search PubMed .
  25. Recent review on ET in zinc myoglobin and methyl viologen 18: K. Tsukahara, M. Okada, S. Asami, Y. Nishikawa, N. Sawai and T. Sakurai, Coord. Chem. Rev., 1994, 132, 223 Search PubMed .
  26. T. Hayashi, A. Tomokuni, T. Takimura and H. Ogoshi, unpublished results..
  27. T. Hayashi, Y. Hitomi and H. Ogoshi, submitted for publication..
  28. J. Lahiri, F. D. Fate, S. B. Ungashe and J. T. Groves, J. Am. Chem. Soc., 1996, 118, 2347 Search PubMed .
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