Self-assembled ionophores from isoguanosine: Diffusion NMR spectroscopy clarifies Cation's and Anion's influence on supramolecular structure

Chemistry - A European Journal

Volumn 13, Issue 7, 2007, Pages 1969-1977

  Evan Salem, Tamar ^a   Frish, Limor ^a   Van Leeuwen, Fijs W B ^b   Reinhoudt, David N ^b   Verboom, Willem ^b   Kaucher, Mark S ^c   Davis, Jeffery T ^c   Cohen, Yoram ^a  

^a TEL AVIV UNIVERSITY   (Israel)

^b UNIVERSITY OF TWENTE   (Netherlands)

^c University of Maryland   (United States)

Author keywords

Anions; Cations; Diffusion NMR spectroscopy; Isoguanosine; Self assembly; Supramolecular chemistry

Indexed keywords

DIFFUSION; LITHIUM COMPOUNDS; MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SELF ASSEMBLY; SOLVENTS;

DIFFUSION NMR SPECTROSCOPY; LIPOPHILIC ISOGUANOSINE; MONOVALENT CATIONS; PENTAMERS;

SUPRAMOLECULAR CHEMISTRY;

EID: 34250644838     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601015     Document Type: Article

References (49)

1. a) J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VCH. Weinheim, 1995;
2. b) J. W. Steed, J. L. Atwood, Supramolecular Chemistry, John Wiley & Sons, New York. 200;
3. c) Comprehensive Supramolecular Chemistry (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vo̊gtle, J.-M. Lehn), Pergamon, Oxford, 1996.
4. a) O. Mayzel, Y. Cohen, J. Chem. Soc. Chem. Commun. 1994, 1901-1902;
5. b) A. Gafni, Y. Cohen, J. Org. Chem. 1997. 62, 120-125;
6. c) L. Frish, F. Sansone, A. Casnati, R. Ungaro, Y. Cohen, J. Org. Chem. 2000, 65, 5026-5030;
7. d) L. Avram, Y. Cohen. J. Org. Chem. 2002, 67, 2639-2644;
8. e) Y. Cohen, L. Avram, L. Frish, Angew. Chem. 2005, 117, 524-560;
9. Angew. Chem. Int. Ed. 2005, 44, 520-554.
10. a) L. Frish, S. E. Matthews, V. Bo̊hmerr, Y. Cohen, J. Chem. Soc. Perkin Trans. 2 1999, 669-671;
11. b) L. Frish, M. O. Vysotsky, S. E. Matthews, V. Bo̊hmer, Y. Cohen, J. Chem. Soc. Perkin Trans. 2 2002, 88-93;
12. c) I., Frish, M. O. Vysotsky, V. Bo̊hmer, Y. Cohen, Dry. Biomol. Chem. 2003, 1, 2011-2014.
13. a) L. Avram, Y. Cohen., J. Am. Chem. Soc. 2002, 124, 15 148-15 149;
14. b) L. Avram, Y. Cohen, Org. Lett. 2002, 4, 4365-4368:
15. c) L. Avram, Y. Cohen, Org. Lett. 2003, 5, 1099-1102;
16. d) L. Avram, Y. Cohen, Org. Lett. 2003, 5, 3329-3332;
17. e) L. Avram, Y. Cohen, J. Am. Chem. Soc. 2004, 126, 11556-11563;
18. f) L. Avram, Y. Cohen, Org. Lett. 2006, 8, 219-222.
19. a) P. Timmerman, J. L. Weidmann, K. A. Jolliffe, L. J. Prins, D. N. Reinhoudt, S. Shinkai, L. Frish, Y. Cohen, J. Chem. Soc. Perkin Trans. 2 2000, 2077-2089;
20. b) T. Megyes, H. Jude, T. Grosz, I. Bako, T. Radnai, G. Tarkanyi, G. Palinkas, P. J. Stang, J. Am. Chem. Soc. 2005, 127, 10731-10738;
21. c) W. H. Otto, M. H. Keefe, K. E. Splan, J. T. Hupp, C. K. Larive, Inorg. Chem. 2002, 41, 6172-6174;
22. d) Y. H. Ko, K. Kim, J.-K. Kang, H. Chun, J. W. Lee, S. Sakamoto, K. Yamaguchi, J. Fettinger, K. Kim, J. Am. Chem. Soc. 2004, 126, 1932-1933;
23. e) M. Tominaga, K. Suzuki, M. Kawano, T. Kusukawa, T. Ozeki, S. Sakamoto, K. Yamguchi, M. Fujita, Angew. Chem. 2004, 116, 5739-5743;
24. Angew. Chem. Int. Ed. 2004, 43, 5621-5625.
25. a) M. Valentini, H. Rüegger, P. S. Pregosin, Helv. Chim. Acta 2001. 84, 2833-2853;
26. b) P. S. Pregosin, P. G. A. Kumar, I. Fernandez, Chem. Rev. 2005, 105, 2977-2998.
27. a) M. S. Kaucher, Y.-F. Lam, S. Pieraccini, G. Gottarelli, J. T. Davis, Chem. Eur. J. 2005, 11, 164-173;
28. h) M. S. Kaucher, W. A. Harrell, Jr., J. T. Davis, J. Am. Chem. Soc. 2006, 128, 38-39;
29. c) A. Wong, R. Ida, L. Spindler, G. Wu, J. Am. Chem. Soc. 2005, 127, 6990-6998.
30. J. T. Davis, S. Tirumala, J. R. Jenssen, E. Radler, D. Fabris, J. Org. Chem. 1995, 60, 4167-4176.
31. a) J. T. Davis, Angew. Chem. 2004, 116, 684-716;
32. Angew. Chem. Int. Ed. 2004, 43, 668-698;
33. h) G. P. Spada, G. Gottarelli, Synlett 2004, 596-602.
34. S. Tirumala. A. L. Marlow, J. T. Davis, J. Am. Chem. Soc. 1997, 119, 5271-5272.
35. M. Cai, A. L. Marlow, J. C. Fettinger, D. Fabris, T. J. Haverlock, B. A. Moyer, J.T. Davis, Angew. Chem. 2000, 112, 1339-1341;
36. Angew. Chem. Int. Ed. 2000, 39, 1283-1285.
37. X. Shi, J. C. Fettinger, M. Cai, J. T. Davis, Angew. Chem. 2000, 112, 3254-3257;
38. Angew. Chem. Int. Ed. 2000, 39, 3124-3127.
39. a) J. C. Chaput, C. Switzer, Proc. Natl. Acad. Sci. USA 1999, 96, 10614-10619;
40. b) F. Seela, C. F. Wei, A. Melenewski, E. Feiling, Nucleosides Nucleotides 1998, 17, 2045-2052;
41. c) F. Seela, R. Kröschel, Bioconjugate Chem. 2001, 12, 1043-1050.
42. M. Meyer, J. Suhnel, J. Phys. Chem. A 2003, 107, 1025-1031.
43. S. C. Lee, J. D. Lamb, M. M. Cai, J. T. Davis, J. Incl. Phenom. Macro. Chem. 2001, 40, 51-57.
44. a) F. W. B. van Leeuwen, X. Shi, J. T. Davis, W. Verboom, D. N. Reinhoudt, J. Am. Chem. Soc. 2004, 126, 16575-16581;
45. b) F. W. B. van Leeuwen, C. J. H. Miermans, H. Beijleveld, T. Tomasberger, J. T. Davis, W. Verboom, D. N. Reinhoudt, Environ. Sci. Technol. 2005, 39, 5455-5459.
46. M. M. Cui, V. Sidorov, Y.-F. Lam, R. A. Flowers II. J. T. Davis. Org. Lett. 2000, 2, 1665-1668.
47. M. M. Cai, X. D. Shi, V. Sidorov, D. Fabris, Y.-F. Lam, J. T. Davis, Tetrahedron 2002, 58, 661-671.
48. S. L. Forman, J. C. Fettinger, S. Pieraccini, G. Gottarelli, J. T. Davis, J. Am. Chem. Soc. 2000, 122, 4060-4067.
49. J. S. Gibbs, C. S. Johnson, Jr., J. Magn. Reson. 1991, W. 395-402.