Allosteric silver(I) ion binding with peripheral π clefts of a ce(IV) double decker porphyrin

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1803-1805

  Ikeda, Masato ^a   Tanida, Tomoyuki ^a   Takeuchi, Masayuki ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CERIUM; PORPHYRIN; SILVER;

ARTICLE; BINDING SITE; CHEMISTRY; METABOLISM;

BINDING SITES; CERIUM; PORPHYRINS; SILVER;

EID: 0034729602     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005807a     Document Type: Article

References (38)

1. (a) Perutz, M. F. Annu. Rev. Biochem. 1979, 48, 327.
2. (b) Monod, J.; Changeux, J.-P.; Jacob, F. J. Mol. Biol. 1963, 6. 306.
3. (c) Perutz, M. F.; Fermi, G.; Luisi, B.; Shaanan, B.; Liddington, R. C. Acc. Chem. Res, 1987, 20, 309.
4. Gramdori, R.; Lavoie, T. A.; Pflumm, M.; Tian. G.; Niersbach, H.; Maas, W. K.; Fairman, R.; Carey, J. J. Mol. Biol. 1995, 254, 150.
5. Burke, R.; Witmer, M. R.; Tredup, J.; Micanovic, R.; Gregor, K. R.; Lahiri, J.; Tramposch, K. M.; Villaframca, J. J. Biochemistry 1995, 34, 15165.
6. (a) Filenko, A. M.; Danilova, V. M.; Sobieszek, A. Biophys. J. 1997, 73, 1593.
7. (b) Modi, S.; Gilham, D. E.; Sutcliffe, M. J.; Lian, L.-Y.; Primrose, W. V.; Wolf, C. R.; Roberts, G. C. K. Biochemistry 1997, 36, 4461.
8. (c) Bruzzese, F. J.; Connelly, P. R. Biochemitry 1997, 36, 10428.
9. (d) Schetz, J. A.; Sibley, D. R. J. Neurochem. 1997, 68, 1990.
10. Traylor, T. G.; Mitchell, M. J.; Ciconene, J. P.; Nelson, S. J. Am. Chem. Soc. 1982, 104, 4986.
11. (a) Rebek, J., Jr. Acc. Chem. Res. 1984, 17, 258.
12. (b) Rebek, J., Jr.; Costello, T.; Marshall, L.; Wattley, R.; Gadwood, R. C.; Onan, K. J. Am. Chem. Soc. 1985, 107, 7481.
13. (c) Ebmeyer E.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 1148.
14. (a) Tabushi, I.; Kugimiya, S.; Kinnaird, M. G.; Sasaki, T. J. Am. Chem. Soc. 1985, 107, 4129.
15. (b) Tabushi, I.; Kugimiya, S. J. Am. Chem. Soc. 1986, 108, 6926.
16. Beer, P. D.; Rothin, A. S. J. Chem. Soc., Chem. Commun. 1988, 52.
17. Petter, R. C.; Salek, J. S.; Sikorski, C. T.; Kumaravel, G.; Lin, F.-T. J. Am. Chem. Soc. 1990, 112, 3860.
18. Schneider, H.-J.; Ref, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 1159.
19. Sijbesma, R. P.; Nolte, R. J. J. Am. Chem. Soc. 1991, 113, 6695.
20. Kobuke, Y.; Y. Satoh. J. Am. Chem. Soc. 1992, 114, 789.
21. Kobayashi, K.; Asakawa, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10307.
22. Takeuchi, M.; Imada, T.; Shinkai, S. J. Am. Chem. Soc. 1996, 118, 10658.
23. Takeuchi, M.; Imada, T.; Shinkai, S. Angew. Chem., Int. Ed. 1998, 37, 2096. It is known that the rate of the porphyrin ring rotation in Ce· bis(porphyrinate) double decker is comparable with or slower than the NMR time scale. However, the allosteric behavior is basically observable for the present "static" equilibrium system as long as porphyrin rings are able to rotate. See the following references: Takeuchi, M.; Imada, T.; Ikeda, M.; Shinkai, S. Tetrahedron Lett. 1998, 39, 7897. Tashiro, K.; Konishi, K.; Aida, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 856.
24. Takeuchi, M.; Imada, T.; Shinkai, S. Angew. Chem., Int. Ed. 1998, 37, 2096. It is known that the rate of the porphyrin ring rotation in Ce· bis(porphyrinate) double decker is comparable with or slower than the NMR time scale. However, the allosteric behavior is basically observable for the present "static" equilibrium system as long as porphyrin rings are able to rotate. See the following references: Takeuchi, M.; Imada, T.; Ikeda, M.; Shinkai, S. Tetrahedron Lett. 1998, 39, 7897. Tashiro, K.; Konishi, K.; Aida, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 856.
25. Takeuchi, M.; Imada, T.; Shinkai, S. Angew. Chem., Int. Ed. 1998, 37, 2096. It is known that the rate of the porphyrin ring rotation in Ce· bis(porphyrinate) double decker is comparable with or slower than the NMR time scale. However, the allosteric behavior is basically observable for the present "static" equilibrium system as long as porphyrin rings are able to rotate. See the following references: Takeuchi, M.; Imada, T.; Ikeda, M.; Shinkai, S. Tetrahedron Lett. 1998, 39, 7897. Tashiro, K.; Konishi, K.; Aida, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 856.
26. Sugasaki, A.; Ikeda, M.; Takeuchi, M.; Robertson, A.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1 1999, 3259.
27. Alkali metal binding with peripheral crown ethers of phthalocyanine double decker was reported: Toupane, T.; Ahsen, V.; Simon, J. J. Am. Chem. Soc. 1994, 116, 5352.
28. Silver(I) ion recognition with aromatic π system: (a) Pierre, J.-L.; Baret, P.; Chautemps, P.; Armand, M. J. Am. Chem. Soc. 1981, 103, 2986.
29. (b) Kang, H. C.; Hanson, A. W.; Eaton, B.; Boekelheide, V. J. Am. Chem. Soc. 1985, 107, 1979.
30. (c) Gano, G.; Subramaniam, G.; Brirnbaum R. J. Org. Chem. 1990, 55, 4760.
31. (d) Ikeda, A.; Tsuzuki, H.; Shinkai, S. J. Chem. Soc. Perkin Trans. 2 1994, 2073.
32. (e) Ikeda, A.; Shinkai, S. J. Am. Chem. Soc. 1994, 116, 3102.
33. (f) Ikeda, A.; Tsudera, T.; Shinkai, S. J. Org. Chem. 1997, 62, 3568 and references therein.
34. Buchler, J. W.; Nawra, M. Inorg. Chem. 1994, 33, 2830.
35. 3: C, 69.21; H, 4.42; N, 6.42. Found C, 69.51; H, 4.79; N, 6.22.
36. Baldwin, J.; Chothia, C. J. Mol. Biol. 1979, 129, 175.
37. (b) Connors, K. A. Binding Constants; John Wiley: New York, 1987.
38. Job, A. Ann. Chim. (10th series) 1928, 9, 113.