A supramolecular ion channel based on amphiphilic cholic acid derivatives

Chemistry Letters

Volumn , Issue 4, 2000, Pages 298-299

  Kobuke, Yoshiaki ^b   Nagatani, Takeshi ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

^b NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034358457     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.298     Document Type: Article

References (23)

1. Review articles are available for reports up to 1997: G. W. Gokel and O. Murillo, Acc. Chem. Res., 29, 425 (1996); T. M. Fyles and van W. F. Straaten-Nijenhuis, "Comprehensive Supramolecular Chemistry," ed by D. N. Reinhoudt, Elsevier Science Ltd., Oxford (1996), Vol. 10, p. 53; N. Voyer, Top. Curr. Chem., 184, 1 (1996); Y. Kobuke, "Advances in Supramolecular Chemistry," ed by G. W. Gokel, JAI Press, Greenwich (1997), Vol. 4, p. 163.
2. Review articles are available for reports up to 1997: G. W. Gokel and O. Murillo, Acc. Chem. Res., 29, 425 (1996); T. M. Fyles and van W. F. Straaten-Nijenhuis, "Comprehensive Supramolecular Chemistry," ed by D. N. Reinhoudt, Elsevier Science Ltd., Oxford (1996), Vol. 10, p. 53; N. Voyer, Top. Curr. Chem., 184, 1 (1996); Y. Kobuke, "Advances in Supramolecular Chemistry," ed by G. W. Gokel, JAI Press, Greenwich (1997), Vol. 4, p. 163.
3. Review articles are available for reports up to 1997: G. W. Gokel and O. Murillo, Acc. Chem. Res., 29, 425 (1996); T. M. Fyles and van W. F. Straaten-Nijenhuis, "Comprehensive Supramolecular Chemistry," ed by D. N. Reinhoudt, Elsevier Science Ltd., Oxford (1996), Vol. 10, p. 53; N. Voyer, Top. Curr. Chem., 184, 1 (1996); Y. Kobuke, "Advances in Supramolecular Chemistry," ed by G. W. Gokel, JAI Press, Greenwich (1997), Vol. 4, p. 163.
4. Review articles are available for reports up to 1997: G. W. Gokel and O. Murillo, Acc. Chem. Res., 29, 425 (1996); T. M. Fyles and van W. F. Straaten-Nijenhuis, "Comprehensive Supramolecular Chemistry," ed by D. N. Reinhoudt, Elsevier Science Ltd., Oxford (1996), Vol. 10, p. 53; N. Voyer, Top. Curr. Chem., 184, 1 (1996); Y. Kobuke, "Advances in Supramolecular Chemistry," ed by G. W. Gokel, JAI Press, Greenwich (1997), Vol. 4, p. 163.
5. More recent examples reported are: C. Ni and S. Matile, Chem. Commun., 1998, 755; L. Chen, N. Sakai, S. T. Moshiri, and S. Matile, Tetrahedron Lett., 39, 3627 (1998); J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, and G. W. Gokel, Angew. Chem., Int. Ed. Engl., 37, 1534 (1998); T. D. Clark, L. K. Buehler, and M. R. Ghadiri, J. Am. Chem. Soc., 120, 651 (1998); T. M. Fyles, D. Loock, and X. Zhou, J. Am. Chem. Soc., 120, 2997 (1998); M. G. Fritz, P. Walde, and D. Seebach, Macromol., 32, 574 (1999); M. M. Tedesco, B. Ghebremariam, N. Sakai, and S. Matile, Angew. Chem., Int. Ed. Engl., 38, 540 (1999); N. Sakai, N. Majumdar, and S. Matile, J. Am. Chem. Soc., 121, 4294 (1999); E. Abel, G. E. M. Maguire, O. Murillo, I. Suzuki, S. L. De Wall, and G. W. Gokel, J. Am. Chem. Soc., 121, 9043 (1999).
6. More recent examples reported are: C. Ni and S. Matile, Chem. Commun., 1998, 755; L. Chen, N. Sakai, S. T. Moshiri, and S. Matile, Tetrahedron Lett., 39, 3627 (1998); J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, and G. W. Gokel, Angew. Chem., Int. Ed. Engl., 37, 1534 (1998); T. D. Clark, L. K. Buehler, and M. R. Ghadiri, J. Am. Chem. Soc., 120, 651 (1998); T. M. Fyles, D. Loock, and X. Zhou, J. Am. Chem. Soc., 120, 2997 (1998); M. G. Fritz, P. Walde, and D. Seebach, Macromol., 32, 574 (1999); M. M. Tedesco, B. Ghebremariam, N. Sakai, and S. Matile, Angew. Chem., Int. Ed. Engl., 38, 540 (1999); N. Sakai, N. Majumdar, and S. Matile, J. Am. Chem. Soc., 121, 4294 (1999); E. Abel, G. E. M. Maguire, O. Murillo, I. Suzuki, S. L. De Wall, and G. W. Gokel, J. Am. Chem. Soc., 121, 9043 (1999).
7. More recent examples reported are: C. Ni and S. Matile, Chem. Commun., 1998, 755; L. Chen, N. Sakai, S. T. Moshiri, and S. Matile, Tetrahedron Lett., 39, 3627 (1998); J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, and G. W. Gokel, Angew. Chem., Int. Ed. Engl., 37, 1534 (1998); T. D. Clark, L. K. Buehler, and M. R. Ghadiri, J. Am. Chem. Soc., 120, 651 (1998); T. M. Fyles, D. Loock, and X. Zhou, J. Am. Chem. Soc., 120, 2997 (1998); M. G. Fritz, P. Walde, and D. Seebach, Macromol., 32, 574 (1999); M. M. Tedesco, B. Ghebremariam, N. Sakai, and S. Matile, Angew. Chem., Int. Ed. Engl., 38, 540 (1999); N. Sakai, N. Majumdar, and S. Matile, J. Am. Chem. Soc., 121, 4294 (1999); E. Abel, G. E. M. Maguire, O. Murillo, I. Suzuki, S. L. De Wall, and G. W. Gokel, J. Am. Chem. Soc., 121, 9043 (1999).
8. More recent examples reported are: C. Ni and S. Matile, Chem. Commun., 1998, 755; L. Chen, N. Sakai, S. T. Moshiri, and S. Matile, Tetrahedron Lett., 39, 3627 (1998); J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, and G. W. Gokel, Angew. Chem., Int. Ed. Engl., 37, 1534 (1998); T. D. Clark, L. K. Buehler, and M. R. Ghadiri, J. Am. Chem. Soc., 120, 651 (1998); T. M. Fyles, D. Loock, and X. Zhou, J. Am. Chem. Soc., 120, 2997 (1998); M. G. Fritz, P. Walde, and D. Seebach, Macromol., 32, 574 (1999); M. M. Tedesco, B. Ghebremariam, N. Sakai, and S. Matile, Angew. Chem., Int. Ed. Engl., 38, 540 (1999); N. Sakai, N. Majumdar, and S. Matile, J. Am. Chem. Soc., 121, 4294 (1999); E. Abel, G. E. M. Maguire, O. Murillo, I. Suzuki, S. L. De Wall, and G. W. Gokel, J. Am. Chem. Soc., 121, 9043 (1999).
9. More recent examples reported are: C. Ni and S. Matile, Chem. Commun., 1998, 755; L. Chen, N. Sakai, S. T. Moshiri, and S. Matile, Tetrahedron Lett., 39, 3627 (1998); J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, and G. W. Gokel, Angew. Chem., Int. Ed. Engl., 37, 1534 (1998); T. D. Clark, L. K. Buehler, and M. R. Ghadiri, J. Am. Chem. Soc., 120, 651 (1998); T. M. Fyles, D. Loock, and X. Zhou, J. Am. Chem. Soc., 120, 2997 (1998); M. G. Fritz, P. Walde, and D. Seebach, Macromol., 32, 574 (1999); M. M. Tedesco, B. Ghebremariam, N. Sakai, and S. Matile, Angew. Chem., Int. Ed. Engl., 38, 540 (1999); N. Sakai, N. Majumdar, and S. Matile, J. Am. Chem. Soc., 121, 4294 (1999); E. Abel, G. E. M. Maguire, O. Murillo, I. Suzuki, S. L. De Wall, and G. W. Gokel, J. Am. Chem. Soc., 121, 9043 (1999).
10. More recent examples reported are: C. Ni and S. Matile, Chem. Commun., 1998, 755; L. Chen, N. Sakai, S. T. Moshiri, and S. Matile, Tetrahedron Lett., 39, 3627 (1998); J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, and G. W. Gokel, Angew. Chem., Int. Ed. Engl., 37, 1534 (1998); T. D. Clark, L. K. Buehler, and M. R. Ghadiri, J. Am. Chem. Soc., 120, 651 (1998); T. M. Fyles, D. Loock, and X. Zhou, J. Am. Chem. Soc., 120, 2997 (1998); M. G. Fritz, P. Walde, and D. Seebach, Macromol., 32, 574 (1999); M. M. Tedesco, B. Ghebremariam, N. Sakai, and S. Matile, Angew. Chem., Int. Ed. Engl., 38, 540 (1999); N. Sakai, N. Majumdar, and S. Matile, J. Am. Chem. Soc., 121, 4294 (1999); E. Abel, G. E. M. Maguire, O. Murillo, I. Suzuki, S. L. De Wall, and G. W. Gokel, J. Am. Chem. Soc., 121, 9043 (1999).
11. More recent examples reported are: C. Ni and S. Matile, Chem. Commun., 1998, 755; L. Chen, N. Sakai, S. T. Moshiri, and S. Matile, Tetrahedron Lett., 39, 3627 (1998); J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, and G. W. Gokel, Angew. Chem., Int. Ed. Engl., 37, 1534 (1998); T. D. Clark, L. K. Buehler, and M. R. Ghadiri, J. Am. Chem. Soc., 120, 651 (1998); T. M. Fyles, D. Loock, and X. Zhou, J. Am. Chem. Soc., 120, 2997 (1998); M. G. Fritz, P. Walde, and D. Seebach, Macromol., 32, 574 (1999); M. M. Tedesco, B. Ghebremariam, N. Sakai, and S. Matile, Angew. Chem., Int. Ed. Engl., 38, 540 (1999); N. Sakai, N. Majumdar, and S. Matile, J. Am. Chem. Soc., 121, 4294 (1999); E. Abel, G. E. M. Maguire, O. Murillo, I. Suzuki, S. L. De Wall, and G. W. Gokel, J. Am. Chem. Soc., 121, 9043 (1999).
12. More recent examples reported are: C. Ni and S. Matile, Chem. Commun., 1998, 755; L. Chen, N. Sakai, S. T. Moshiri, and S. Matile, Tetrahedron Lett., 39, 3627 (1998); J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, and G. W. Gokel, Angew. Chem., Int. Ed. Engl., 37, 1534 (1998); T. D. Clark, L. K. Buehler, and M. R. Ghadiri, J. Am. Chem. Soc., 120, 651 (1998); T. M. Fyles, D. Loock, and X. Zhou, J. Am. Chem. Soc., 120, 2997 (1998); M. G. Fritz, P. Walde, and D. Seebach, Macromol., 32, 574 (1999); M. M. Tedesco, B. Ghebremariam, N. Sakai, and S. Matile, Angew. Chem., Int. Ed. Engl., 38, 540 (1999); N. Sakai, N. Majumdar, and S. Matile, J. Am. Chem. Soc., 121, 4294 (1999); E. Abel, G. E. M. Maguire, O. Murillo, I. Suzuki, S. L. De Wall, and G. W. Gokel, J. Am. Chem. Soc., 121, 9043 (1999).
13. More recent examples reported are: C. Ni and S. Matile, Chem. Commun., 1998, 755; L. Chen, N. Sakai, S. T. Moshiri, and S. Matile, Tetrahedron Lett., 39, 3627 (1998); J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, and G. W. Gokel, Angew. Chem., Int. Ed. Engl., 37, 1534 (1998); T. D. Clark, L. K. Buehler, and M. R. Ghadiri, J. Am. Chem. Soc., 120, 651 (1998); T. M. Fyles, D. Loock, and X. Zhou, J. Am. Chem. Soc., 120, 2997 (1998); M. G. Fritz, P. Walde, and D. Seebach, Macromol., 32, 574 (1999); M. M. Tedesco, B. Ghebremariam, N. Sakai, and S. Matile, Angew. Chem., Int. Ed. Engl., 38, 540 (1999); N. Sakai, N. Majumdar, and S. Matile, J. Am. Chem. Soc., 121, 4294 (1999); E. Abel, G. E. M. Maguire, O. Murillo, I. Suzuki, S. L. De Wall, and G. W. Gokel, J. Am. Chem. Soc., 121, 9043 (1999).
14. Y. Kobuke, K. Ueda, and M. Sokabe, J. Am. Chem. Soc., 114, 7618 (1992); Y. Tanaka, Y. Kobuke, and M. Sokabe, Angew. Chem., Int. Ed. Engl., 34, 693 (1995); Y. Kobuke, K. Ueda, and M. Sokabe, Chem. Lett., 1995, 435; Y. Kobuke and K. Morita, Inorg. Chim. Acta, 283, 167 (1998); Y. Kobuke and A. Ohgoshi, Colloids and Surfaces A, in press.
15. Y. Kobuke, K. Ueda, and M. Sokabe, J. Am. Chem. Soc., 114, 7618 (1992); Y. Tanaka, Y. Kobuke, and M. Sokabe, Angew. Chem., Int. Ed. Engl., 34, 693 (1995); Y. Kobuke, K. Ueda, and M. Sokabe, Chem. Lett., 1995, 435; Y. Kobuke and K. Morita, Inorg. Chim. Acta, 283, 167 (1998); Y. Kobuke and A. Ohgoshi, Colloids and Surfaces A, in press.
16. Y. Kobuke, K. Ueda, and M. Sokabe, J. Am. Chem. Soc., 114, 7618 (1992); Y. Tanaka, Y. Kobuke, and M. Sokabe, Angew. Chem., Int. Ed. Engl., 34, 693 (1995); Y. Kobuke, K. Ueda, and M. Sokabe, Chem. Lett., 1995, 435; Y. Kobuke and K. Morita, Inorg. Chim. Acta, 283, 167 (1998); Y. Kobuke and A. Ohgoshi, Colloids and Surfaces A, in press.
17. Y. Kobuke, K. Ueda, and M. Sokabe, J. Am. Chem. Soc., 114, 7618 (1992); Y. Tanaka, Y. Kobuke, and M. Sokabe, Angew. Chem., Int. Ed. Engl., 34, 693 (1995); Y. Kobuke, K. Ueda, and M. Sokabe, Chem. Lett., 1995, 435; Y. Kobuke and K. Morita, Inorg. Chim. Acta, 283, 167 (1998); Y. Kobuke and A. Ohgoshi, Colloids and Surfaces A, in press.
18. Y. Kobuke, K. Ueda, and M. Sokabe, J. Am. Chem. Soc., 114, 7618 (1992); Y. Tanaka, Y. Kobuke, and M. Sokabe, Angew. Chem., Int. Ed. Engl., 34, 693 (1995); Y. Kobuke, K. Ueda, and M. Sokabe, Chem. Lett., 1995, 435; Y. Kobuke and K. Morita, Inorg. Chim. Acta, 283, 167 (1998); Y. Kobuke and A. Ohgoshi, Colloids and Surfaces A, in press.
19. 3): δ 3.65 (s, 3H), 3.34 (m, 1H), 3.31 (s, 3H), 3.23 (s, 3H), 3.19 (s, 3H), 3.12 (m, 1H), 2.98 (m, 1H), 2.40-0.60 (m, 33H).
20. -1 (OH).
21. 3) δ 3.49 (m, 2H), 3.36 (m, 1H), 3.32 (s, 3H), 3.24 (s, 3H), 3.20 (s, 3H), 3.17 (m, 1H), 2.97 (m, 1H), 2.4-0.6 (m, 33H).
22. +).
23. B. Hille, "Ionic Channels of Excitable Membranes," 2nd ed, Sinauer, Sunderland, MA (1992).