Porphyrin receptors for amines, amino acids, and oligopeptides in water

Journal of the American Chemical Society

Volumn 121, Issue 49, 1999, Pages 11425-11431

  Mizutani, Tadashi ^a   Wada, Kenji ^a   Kitagawa, Susumu ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ESTER; OLIGOPEPTIDE; PORPHYRIN; RECEPTOR; ZINC DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; HYDROPHILICITY; MOLECULAR RECOGNITION;

EID: 0033572889     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9922126     Document Type: Article

References (38)

1. For recent studies on molecular recognition in water, see: (a) Schneider, H.-J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442. (b) Kral, V.; Furuta, H.; Shreder, K.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1595. (c) Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993. (d) Dandliker, P. J.; Diederich, F.; Zingg, A.; Gisselbrecht, J. P.; Gross, M.; Louati, A.; Sanford, E. Helv. Chim. Acta 1997, 80, 1773. (e) Nelen, M. I.; Eliseev, A. V. J. Chem. Soc., Perkin Trans. 2 1997, 1359. (f) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649. (g) Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208. (h) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8. (i) Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192. (j) Inouye, M.; Fujimoto, K.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 1452. (k) Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907.
2. For recent studies on molecular recognition in water, see: (a) Schneider, H.-J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442. (b) Kral, V.; Furuta, H.; Shreder, K.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1595. (c) Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993. (d) Dandliker, P. J.; Diederich, F.; Zingg, A.; Gisselbrecht, J. P.; Gross, M.; Louati, A.; Sanford, E. Helv. Chim. Acta 1997, 80, 1773. (e) Nelen, M. I.; Eliseev, A. V. J. Chem. Soc., Perkin Trans. 2 1997, 1359. (f) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649. (g) Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208. (h) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8. (i) Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192. (j) Inouye, M.; Fujimoto, K.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 1452. (k) Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907.
3. For recent studies on molecular recognition in water, see: (a) Schneider, H.-J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442. (b) Kral, V.; Furuta, H.; Shreder, K.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1595. (c) Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993. (d) Dandliker, P. J.; Diederich, F.; Zingg, A.; Gisselbrecht, J. P.; Gross, M.; Louati, A.; Sanford, E. Helv. Chim. Acta 1997, 80, 1773. (e) Nelen, M. I.; Eliseev, A. V. J. Chem. Soc., Perkin Trans. 2 1997, 1359. (f) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649. (g) Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208. (h) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8. (i) Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192. (j) Inouye, M.; Fujimoto, K.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 1452. (k) Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907.
4. For recent studies on molecular recognition in water, see: (a) Schneider, H.-J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442. (b) Kral, V.; Furuta, H.; Shreder, K.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1595. (c) Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993. (d) Dandliker, P. J.; Diederich, F.; Zingg, A.; Gisselbrecht, J. P.; Gross, M.; Louati, A.; Sanford, E. Helv. Chim. Acta 1997, 80, 1773. (e) Nelen, M. I.; Eliseev, A. V. J. Chem. Soc., Perkin Trans. 2 1997, 1359. (f) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649. (g) Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208. (h) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8. (i) Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192. (j) Inouye, M.; Fujimoto, K.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 1452. (k) Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907.
5. For recent studies on molecular recognition in water, see: (a) Schneider, H.-J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442. (b) Kral, V.; Furuta, H.; Shreder, K.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1595. (c) Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993. (d) Dandliker, P. J.; Diederich, F.; Zingg, A.; Gisselbrecht, J. P.; Gross, M.; Louati, A.; Sanford, E. Helv. Chim. Acta 1997, 80, 1773. (e) Nelen, M. I.; Eliseev, A. V. J. Chem. Soc., Perkin Trans. 2 1997, 1359. (f) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649. (g) Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208. (h) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8. (i) Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192. (j) Inouye, M.; Fujimoto, K.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 1452. (k) Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907.
6. For recent studies on molecular recognition in water, see: (a) Schneider, H.-J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442. (b) Kral, V.; Furuta, H.; Shreder, K.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1595. (c) Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993. (d) Dandliker, P. J.; Diederich, F.; Zingg, A.; Gisselbrecht, J. P.; Gross, M.; Louati, A.; Sanford, E. Helv. Chim. Acta 1997, 80, 1773. (e) Nelen, M. I.; Eliseev, A. V. J. Chem. Soc., Perkin Trans. 2 1997, 1359. (f) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649. (g) Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208. (h) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8. (i) Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192. (j) Inouye, M.; Fujimoto, K.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 1452. (k) Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907.
7. For recent studies on molecular recognition in water, see: (a) Schneider, H.-J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442. (b) Kral, V.; Furuta, H.; Shreder, K.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1595. (c) Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993. (d) Dandliker, P. J.; Diederich, F.; Zingg, A.; Gisselbrecht, J. P.; Gross, M.; Louati, A.; Sanford, E. Helv. Chim. Acta 1997, 80, 1773. (e) Nelen, M. I.; Eliseev, A. V. J. Chem. Soc., Perkin Trans. 2 1997, 1359. (f) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649. (g) Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208. (h) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8. (i) Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192. (j) Inouye, M.; Fujimoto, K.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 1452. (k) Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907.
8. For recent studies on molecular recognition in water, see: (a) Schneider, H.-J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442. (b) Kral, V.; Furuta, H.; Shreder, K.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1595. (c) Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993. (d) Dandliker, P. J.; Diederich, F.; Zingg, A.; Gisselbrecht, J. P.; Gross, M.; Louati, A.; Sanford, E. Helv. Chim. Acta 1997, 80, 1773. (e) Nelen, M. I.; Eliseev, A. V. J. Chem. Soc., Perkin Trans. 2 1997, 1359. (f) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649. (g) Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208. (h) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8. (i) Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192. (j) Inouye, M.; Fujimoto, K.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 1452. (k) Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907.
9. For recent studies on molecular recognition in water, see: (a) Schneider, H.-J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442. (b) Kral, V.; Furuta, H.; Shreder, K.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1595. (c) Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993. (d) Dandliker, P. J.; Diederich, F.; Zingg, A.; Gisselbrecht, J. P.; Gross, M.; Louati, A.; Sanford, E. Helv. Chim. Acta 1997, 80, 1773. (e) Nelen, M. I.; Eliseev, A. V. J. Chem. Soc., Perkin Trans. 2 1997, 1359. (f) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649. (g) Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208. (h) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8. (i) Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192. (j) Inouye, M.; Fujimoto, K.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 1452. (k) Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907.
10. For recent studies on molecular recognition in water, see: (a) Schneider, H.-J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442. (b) Kral, V.; Furuta, H.; Shreder, K.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1595. (c) Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993. (d) Dandliker, P. J.; Diederich, F.; Zingg, A.; Gisselbrecht, J. P.; Gross, M.; Louati, A.; Sanford, E. Helv. Chim. Acta 1997, 80, 1773. (e) Nelen, M. I.; Eliseev, A. V. J. Chem. Soc., Perkin Trans. 2 1997, 1359. (f) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649. (g) Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208. (h) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8. (i) Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192. (j) Inouye, M.; Fujimoto, K.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 1452. (k) Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907.
11. For recent studies on molecular recognition in water, see: (a) Schneider, H.-J.; Kramer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442. (b) Kral, V.; Furuta, H.; Shreder, K.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1996, 118, 1595. (c) Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993. (d) Dandliker, P. J.; Diederich, F.; Zingg, A.; Gisselbrecht, J. P.; Gross, M.; Louati, A.; Sanford, E. Helv. Chim. Acta 1997, 80, 1773. (e) Nelen, M. I.; Eliseev, A. V. J. Chem. Soc., Perkin Trans. 2 1997, 1359. (f) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649. (g) Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208. (h) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8. (i) Ngola, S. M.; Kearney, P. C.; Mecozzi, S.; Russell, K.; Dougherty, D. A. J. Am. Chem. Soc. 1999, 121, 1192. (j) Inouye, M.; Fujimoto, K.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 1452. (k) Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907.
12. Adrian, J. C., Jr.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 678.
13. Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875.
14. (a) Tabushi, I.; Shimizu, N.; Sugimoto, T.; Shiozuka, M.; Yamamura, K. J. Am. Chem. Soc. 1977, 99, 7100.
15. (b) Tabushi, I.; Kuroda, Y.; Mizutani, T. Tetrahedron 1984, 40, 545.
16. (c) Tabushi, I.; Kuroda, Y.; Mizutani, T. J. Am. Chem. Soc. 1986, 108, 4514.
17. For amino acids recognition in water by zinc porphyrins, see: (a) Mikros, E.; Gaudemer, A.; Pasternack, R. Inorg. Chim. Acta 1988, 153, 199. (b) Konishi, K.; Yahara, K.; Toshishige, H.; Aida, T.; Inoue, S. J. Am. Chem. Soc. 1994, 116, 1337.
18. For amino acids recognition in water by zinc porphyrins, see: (a) Mikros, E.; Gaudemer, A.; Pasternack, R. Inorg. Chim. Acta 1988, 153, 199. (b) Konishi, K.; Yahara, K.; Toshishige, H.; Aida, T.; Inoue, S. J. Am. Chem. Soc. 1994, 116, 1337.
19. Borchardt, R. T.; Sinhababu, A. K. J. Org. Chem. 1981, 46, 5021.
20. Lindsey, J. S.; Wagner, R. W. J. Org. Chem. 1989, 54, 828.
21. Rabenstein, D. L.; Bratt, P.; Peng, J. Biochemistry 1998, 37, 14121.
22. -1. See: Hosseini, M. W.; Lehn, J.-M.; Mertes, M. P. Helv. Chim. Acta 1983, 66, 2454. See also: Gokel, G. W.; Abel, E. Comprehensive Supramolecular Chemistry; Gokel, G. W., Ed.; Pergamon Press Ltd.: Oxford, 1996; Vol. 1, p 511. Mock, W. L.; Shin, N.-Y. J. Org. Chem. 1986, 51, 4440.
23. -1. See: Hosseini, M. W.; Lehn, J.-M.; Mertes, M. P. Helv. Chim. Acta 1983, 66, 2454. See also: Gokel, G. W.; Abel, E. Comprehensive Supramolecular Chemistry; Gokel, G. W., Ed.; Pergamon Press Ltd.: Oxford, 1996; Vol. 1, p 511. Mock, W. L.; Shin, N.-Y. J. Org. Chem. 1986, 51, 4440.
24. -1. See: Hosseini, M. W.; Lehn, J.-M.; Mertes, M. P. Helv. Chim. Acta 1983, 66, 2454. See also: Gokel, G. W.; Abel, E. Comprehensive Supramolecular Chemistry; Gokel, G. W., Ed.; Pergamon Press Ltd.: Oxford, 1996; Vol. 1, p 511. Mock, W. L.; Shin, N.-Y. J. Org. Chem. 1986, 51, 4440.
25. Hossain, M. A.; Schneider, H.-J. Chem. Eur. J. 1999, 5, 1284.
26. Breslow, R.; Chung, S. J. Am. Chem. Soc. 1990, 112, 9659.
27. Hay, R. W.; Morris, P. J. J. Chem. Soc. B 1970, 1577.
28. Verchére-Bèaur, C.; Mikros, E.; Perree-Fauvet, M.; Gaudemer, A. J. Inorg. Biochem. 1990, 40, 127.
29. Similar complexation-induced shifts were also observed for the complex between 3 and Ala-OMe, so that the shifts observed for the pyridine complex are not ascribed to the ring current effects of pyridine.
30. Profound steric effects on binding by a zinc porphyrin were reported: Bhyrappa, P.; Vaijayanthimala, G.; Suslick, K. S. J. Am. Chem. Soc. 1999, 121, 262.
31. Imai, H.; Nakagawa, S.; Kyuno, E. J. Am. Chem. Soc. 1992, 114, 6719. Kuroda, Y.; Kato, Y.; Higashioji, T.; Hasegawa, J.; Kawanami, S.; Takahashi, M.; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. Mizutani, T.; Murakami, T.; Kurahashi, T.; Ogoshi, H. J. Org. Chem. 1996, 61, 539.
32. Imai, H.; Nakagawa, S.; Kyuno, E. J. Am. Chem. Soc. 1992, 114, 6719. Kuroda, Y.; Kato, Y.; Higashioji, T.; Hasegawa, J.; Kawanami, S.; Takahashi, M.; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. Mizutani, T.; Murakami, T.; Kurahashi, T.; Ogoshi, H. J. Org. Chem. 1996, 61, 539.
33. Imai, H.; Nakagawa, S.; Kyuno, E. J. Am. Chem. Soc. 1992, 114, 6719. Kuroda, Y.; Kato, Y.; Higashioji, T.; Hasegawa, J.; Kawanami, S.; Takahashi, M.; Shiraishi, N.; Tanabe, K.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 10950. Mizutani, T.; Murakami, T.; Kurahashi, T.; Ogoshi, H. J. Org. Chem. 1996, 61, 539.
34. Lamry, R.; Rajender, S. Biopolymers 1970, 9, 1125-1227.
35. Mizutani, T.; Horiguchi, T.; Koyama, H.; Uratani, I.; Ogoshi, H. Bull. Chem. Soc. Jpn. 1998, 71, 413.
36. Kitae, T.; Nakayama, T.; Kano, K. J. Chem. Soc., Perkin Trans. 2 1998, 207-212
37. Formation of some crown ether-metal cation complexes is entropically driven, see: Bradshaw, J. S.; Izatt, R. M.; Bordunov, A. V.; Zhu, C. Y.; Hathaway, J. K. Comprehensive Supramolecular Chemistry; Gokel, G. W., Ed.; Pergamon Press Ltd.: Oxford, 1996; Vol. 1, p 35.
38. The least-squares fitting was performed by the computer program SPANA, kindly provided by Prof. Y. Kuroda, Department of Polymer Science, Kyoto Institute of Technology, Matsugasaki, Kyoto 606-8585, Japan. e-mail: ykuroda@ipc.kit.ac.jp.