Strong Positive Allosterism which Appears in Molecular Recognition with Cerium(IV) Double Decker Porphyrins: 'Correlation between the Number of Binding Sites and Hill Coefficients

Supramolecular Chemistry

Volumn 12, Issue 3, 2000, Pages 321-345

  Ikeda, Masato ^a   Takeuchi, Masayuki ^a   Sugasaki, Atsushi ^a   Robertson, Andrew ^a   Imada, Tomoyuki ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Chirality; Crystal structure; Double decker porphyrins; Molecular recognition; Positive allosterism

Indexed keywords

EID: 0034562964     PISSN: 10610278     EISSN: None     Source Type: Journal    
DOI: 10.1080/10610270008029453     Document Type: Article

References (45)

1. (a) Perutz, M. F. (1979). Ann. Rev. Biochem., 48, 327.
2. (b) Monod, J., Changeux, J.-P. and Jacob, F. (1963). J. Mol. Biol., 6, 306.
3. (c) Perutz, M. F., Fermi, G., Luisi, B., Shaanan, B. and Liddington, R. C. (1987). Acc. Chem. Res., 20, 309.
4. Gramdori, R., Lavoie, T. A., Pflumm, M., Tian, G., Niersbach, H., Maas, W. K., Fairman, R. and Carey, J. (1995). J. Mol. Biol., 254, 150.
5. Burke, J. R., Witmer, M. R., Tredup, J., Micanovic, R., Gregor, K. R., Lahiri, J., Tramposch, K. M. and Villaframca, J.J. (1995). Biochemistry, 34, 15165.
6. (a) Filenko, A. M., Danilova, V. M. and Sobieszek, A. (1997). Biophys. J., 73, 1593.
7. (b) Modi, S., Gilham, D. E., Sutcliffe, M. J., Lian, L.-Y., Primrose, W. V., Wolf, C. R. and Roberts, G. C. K. (1997). Biochemistry, 36, 4461.
8. (c) Bruzzese, F. J. and Connelly, P. R. (1997). ibid., 36, 10428.
9. (d) Schetz, J. A. and Sibley, D. R. (1997). J. Neurochem., 68, 1990.
10. Traylor, T. G., Mitchell, M. J., Ciconene, J. P. and Nelson, S. (1982). J. Am. Chem. Soc., 104, 4986.
11. (a) Rebek, J. Jr. (1984). Acc. Chem. Res., 17, 258.
12. (b) Rebek, J. Jr., Costello, T., Marshall, L., Wattley, R., Gadwood, R. C. and Onan, K. (1985). J. Am. Chem. Soc., 107, 7481.
13. (a) Tabushi, I., Kugimiya, S., Kinnaird, M. G. and Sasaki, T. (1985). J. Am. Chem. Soc., 107, 4129.
14. (b) Tabushi, I. and Kugimiya, S. (1986). ibid., 108, 6926.
15. Beer, P. D. and Rothin, A. S. (1988). J. Chem. Soc., Chem. Commun., 52.
16. Petter, R. C., Salek, J. S., Sikorski, C. T., Kumaravel, G. and Lin, F.-T. (1990). J. Am. Chem. Soc., 112, 3860.
17. Schneider, H.-J. and Ref, D. (1990). Angew. Chem. Int. Ed. Engl., 29, 1159.
18. Sijbesma, R. P. and Nolte, R. J. (1991). J. Am. Chem. Soc., 113, 6695.
19. Kobuke, Y. and Satoh, Y. (1992). J. Am. Chem. Soc., 114, 789.
20. (a) Kobayashi, K., Asakawa, Y., Kato, Y. and Aoyama, Y. (1992). J. Am. Chem. Soc., 114, 10307.
21. (b) Blanc, S., Yakirevitch, P., Leize, E., Meyer, M., Libman, J., VanDorsselaer, A., Albrecht-Gray, A. M. and Shanzer, A. (1997). J. Am. Chem. Soc., 119, 4934.
22. (c) Glass, T. E. (2000). J. Am. Chem. Soc., 122, 4522.
23. Takeuchi, M., Imada, T. and Shinkai, S. (1996). J. Am. Chem. Soc., 118, 10658 and references cited therein.
24. For the syntheses of metal bis(porphyrinate) double deckers see (a) Buchler, J. W. and Nawra, M. (1994). Inorg. Chem., 33, 2830. (b) Buchler, J. W., Eiermann, V., Hanssum, H.; Heinz, G., Rüterjans, H. and Schwarzkopf, M. (1994). Chem. Ber., 127, 589. (c) Buchler, J. W., De Cian, A., Fischer, J., Hammerschmitt, P., Löffler, J., Scharbert, B. and Weiss, R. (1989). ibid., 122, 2219. (d) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 1073. (e) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 201 and references cited therein. (f) Jiang, J., Machida, K., Yamamoto, E. and Adachi, G. (1991). Chem. Lett., 2035. (g) Jiang, J., Machida, K. and Adachi, G. (1992). Bull. Chem. Soc. Jpn., 65, 1990. (h) Jiang, J., Machida, K. and Adachi, G. (1993). J. Alloys. Comp., 32, 950 and references cited therein.
25. For the syntheses of metal bis(porphyrinate) double deckers see (a) Buchler, J. W. and Nawra, M. (1994). Inorg. Chem., 33, 2830. (b) Buchler, J. W., Eiermann, V., Hanssum, H.; Heinz, G., Rüterjans, H. and Schwarzkopf, M. (1994). Chem. Ber., 127, 589. (c) Buchler, J. W., De Cian, A., Fischer, J., Hammerschmitt, P., Löffler, J., Scharbert, B. and Weiss, R. (1989). ibid., 122, 2219. (d) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 1073. (e) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 201 and references cited therein. (f) Jiang, J., Machida, K., Yamamoto, E. and Adachi, G. (1991). Chem. Lett., 2035. (g) Jiang, J., Machida, K. and Adachi, G. (1992). Bull. Chem. Soc. Jpn., 65, 1990. (h) Jiang, J., Machida, K. and Adachi, G. (1993). J. Alloys. Comp., 32, 950 and references cited therein.
26. For the syntheses of metal bis(porphyrinate) double deckers see (a) Buchler, J. W. and Nawra, M. (1994). Inorg. Chem., 33, 2830. (b) Buchler, J. W., Eiermann, V., Hanssum, H.; Heinz, G., Rüterjans, H. and Schwarzkopf, M. (1994). Chem. Ber., 127, 589. (c) Buchler, J. W., De Cian, A., Fischer, J., Hammerschmitt, P., Löffler, J., Scharbert, B. and Weiss, R. (1989). ibid., 122, 2219. (d) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 1073. (e) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 201 and references cited therein. (f) Jiang, J., Machida, K., Yamamoto, E. and Adachi, G. (1991). Chem. Lett., 2035. (g) Jiang, J., Machida, K. and Adachi, G. (1992). Bull. Chem. Soc. Jpn., 65, 1990. (h) Jiang, J., Machida, K. and Adachi, G. (1993). J. Alloys. Comp., 32, 950 and references cited therein.
27. For the syntheses of metal bis(porphyrinate) double deckers see (a) Buchler, J. W. and Nawra, M. (1994). Inorg. Chem., 33, 2830. (b) Buchler, J. W., Eiermann, V., Hanssum, H.; Heinz, G., Rüterjans, H. and Schwarzkopf, M. (1994). Chem. Ber., 127, 589. (c) Buchler, J. W., De Cian, A., Fischer, J., Hammerschmitt, P., Löffler, J., Scharbert, B. and Weiss, R. (1989). ibid., 122, 2219. (d) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 1073. (e) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 201 and references cited therein. (f) Jiang, J., Machida, K., Yamamoto, E. and Adachi, G. (1991). Chem. Lett., 2035. (g) Jiang, J., Machida, K. and Adachi, G. (1992). Bull. Chem. Soc. Jpn., 65, 1990. (h) Jiang, J., Machida, K. and Adachi, G. (1993). J. Alloys. Comp., 32, 950 and references cited therein.
28. For the syntheses of metal bis(porphyrinate) double deckers see (a) Buchler, J. W. and Nawra, M. (1994). Inorg. Chem., 33, 2830. (b) Buchler, J. W., Eiermann, V., Hanssum, H.; Heinz, G., Rüterjans, H. and Schwarzkopf, M. (1994). Chem. Ber., 127, 589. (c) Buchler, J. W., De Cian, A., Fischer, J., Hammerschmitt, P., Löffler, J., Scharbert, B. and Weiss, R. (1989). ibid., 122, 2219. (d) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 1073. (e) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 201 and references cited therein. (f) Jiang, J., Machida, K., Yamamoto, E. and Adachi, G. (1991). Chem. Lett., 2035. (g) Jiang, J., Machida, K. and Adachi, G. (1992). Bull. Chem. Soc. Jpn., 65, 1990. (h) Jiang, J., Machida, K. and Adachi, G. (1993). J. Alloys. Comp., 32, 950 and references cited therein.
29. For the syntheses of metal bis(porphyrinate) double deckers see (a) Buchler, J. W. and Nawra, M. (1994). Inorg. Chem., 33, 2830. (b) Buchler, J. W., Eiermann, V., Hanssum, H.; Heinz, G., Rüterjans, H. and Schwarzkopf, M. (1994). Chem. Ber., 127, 589. (c) Buchler, J. W., De Cian, A., Fischer, J., Hammerschmitt, P., Löffler, J., Scharbert, B. and Weiss, R. (1989). ibid., 122, 2219. (d) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 1073. (e) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 201 and references cited therein. (f) Jiang, J., Machida, K., Yamamoto, E. and Adachi, G. (1991). Chem. Lett., 2035. (g) Jiang, J., Machida, K. and Adachi, G. (1992). Bull. Chem. Soc. Jpn., 65, 1990. (h) Jiang, J., Machida, K. and Adachi, G. (1993). J. Alloys. Comp., 32, 950 and references cited therein.
30. For the syntheses of metal bis(porphyrinate) double deckers see (a) Buchler, J. W. and Nawra, M. (1994). Inorg. Chem., 33, 2830. (b) Buchler, J. W., Eiermann, V., Hanssum, H.; Heinz, G., Rüterjans, H. and Schwarzkopf, M. (1994). Chem. Ber., 127, 589. (c) Buchler, J. W., De Cian, A., Fischer, J., Hammerschmitt, P., Löffler, J., Scharbert, B. and Weiss, R. (1989). ibid., 122, 2219. (d) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 1073. (e) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 201 and references cited therein. (f) Jiang, J., Machida, K., Yamamoto, E. and Adachi, G. (1991). Chem. Lett., 2035. (g) Jiang, J., Machida, K. and Adachi, G. (1992). Bull. Chem. Soc. Jpn., 65, 1990. (h) Jiang, J., Machida, K. and Adachi, G. (1993). J. Alloys. Comp., 32, 950 and references cited therein.
31. For the syntheses of metal bis(porphyrinate) double deckers see (a) Buchler, J. W. and Nawra, M. (1994). Inorg. Chem., 33, 2830. (b) Buchler, J. W., Eiermann, V., Hanssum, H.; Heinz, G., Rüterjans, H. and Schwarzkopf, M. (1994). Chem. Ber., 127, 589. (c) Buchler, J. W., De Cian, A., Fischer, J., Hammerschmitt, P., Löffler, J., Scharbert, B. and Weiss, R. (1989). ibid., 122, 2219. (d) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 1073. (e) Buchler, J. W. and Heinz, G. (1996). ibid., 129, 201 and references cited therein. (f) Jiang, J., Machida, K., Yamamoto, E. and Adachi, G. (1991). Chem. Lett., 2035. (g) Jiang, J., Machida, K. and Adachi, G. (1992). Bull. Chem. Soc. Jpn., 65, 1990. (h) Jiang, J., Machida, K. and Adachi, G. (1993). J. Alloys. Comp., 32, 950 and references cited therein.
32. (a) Tashiro, K., Konishi, K. and Aida, T. (1997). Angew. Chem. Int. Ed., 36, 856.
33. (b) Tashiro, K., Fujiwara, T., Konishi, T. and Aida, T. (1998). Chem. Commun., 1121.
34. It is known that the rate of the porphyrin ring rotation in cerium(IV) double decker porphyrins is comparable with or slower than the NMR time-scale: see Ref. (16) and Takeuchi, M., Imada, T., Ikeda, M. and Shinkai, S. (1998). Tetrahedron Lett., 39, 7897. However, allosteric behavior is observable for the present system as long as the porphyrin rings rotate.
35. Preliminary communication: Takeuchi, M., Imada, T. and Shinkai, S. (1998). Angew. Chem. Int. Ed., 37, 2096. Application of an related system to a memory storage was recently shown: Sugasaki, A., Ikeda, M., Takeuchi, M., Robertson, A. and Shinkai, S. (1999). J. Chem. Soc., Perkin Trans. 2, 3259.
36. Preliminary communication: Takeuchi, M., Imada, T. and Shinkai, S. (1998). Angew. Chem. Int. Ed., 37, 2096. Application of an related system to a memory storage was recently shown: Sugasaki, A., Ikeda, M., Takeuchi, M., Robertson, A. and Shinkai, S. (1999). J. Chem. Soc., Perkin Trans. 2, 3259.
37. (a) Baldwin, J. and Chothia, C. (1979). J. Mol Biol., 129, 175.
38. (b) Connors, K. A. (1987). Binding Constants, John Wiley, New York.
39. Job, A. (1928). Annales de Chimie (10th series), 9, 113.
40. 3.8. The slight deviation from the 1:4 stoichiometry is presumably due to the immediate precipitation after mixing. Although the stoichiometry in the precipitate does not always agree with that in the solution, this can be supporting evidence for the 1:4 stoichiometry.
41. Benesi, H.A. and Hildebrand, J. H. (1949). J. Am. Chem. Soc., 71, 2703..
42. Adler, A. D., Longo, F. R., Finarelli, J. D., Goldmachen, J., Assour, J. and Korsalioff, L. (1967). J. Org. Chem., 32, 476.
43. SIR 97: Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Polidori, G., Spagna, R. and Viterbo, D. (1989). J. Appl. Cryst., 22, 389.
44. DIRDIF 94: The DIRDIF program system, Beurskens, P. T., Admiraal, G., Bosman, W. P., de Gelder, R., Israel, R. and Smits, J. M. M. (1994). University of Nijimegen, The Netherlands.
45. teXsan: Crystal Structure Analysis Package, Molecular Structure Corporation (1985 and 1992).