Selective stabilization of self-assembled hydrogen-bonded molecular capsules through π-π Interactions

Journal of the American Chemical Society

Volumn 134, Issue 6, 2012, Pages 2914-2917

  Tiefenbacher, Konrad ^a   Rebek, Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL MACROMOLECULE; MOLECULAR CAPSULE; NONCOVALENT; SELF-ASSEMBLED;

SYNTHESIS (CHEMICAL);

CHEMISTRY;

DNA; LIGAND; PROTEIN;

ARTICLE; HYDROGEN BOND; LIGAND BINDING; MACROMOLECULE; MOLECULAR INTERACTION; MOLECULAR MODEL; PROTEIN FOLDING; THERMOSTABILITY;

CAPSULES; CHEMISTRY, ORGANIC; CHEMISTRY, PHYSICAL; DIMERIZATION; DNA; HYDROGEN; HYDROGEN BONDING; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PROTEIN CONFORMATION; PROTEIN FOLDING; PROTEINS; UREA;

EID: 84856935555     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja211410x     Document Type: Article

References (42)

1. Castellano, R. K.; Meyer, E. A.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210
2. Salonen, L. M.; Ellermann, M.; Diederich, F. Angew. Chem., Int. Ed. 2011, 50, 4808
3. Bissantz, C.; Kuhn, B.; Stahl, M. J. Med. Chem. 2010, 53, 5061
4. Sherman, J. C. Tetrahedron 1995, 51, 3395
5. Avram, L.; Cohen, Y. J. Am. Chem. Soc. 2004, 126, 11556
6. Shivanyuk, A.; Rebek, J., Jr. Chem. Commun. 2001, 2424
7. Kerckhoffs, J. M. C. A.; ten Cate, M. G. J.; Mateos-Timoneda, M. A.; van Leeuwen, F. W. B.; Snellink-Ruel, B.; Spek, A. L.; Kooijman, H.; Crego-Calama, M.; Reinhoudt, D. N. J. Am. Chem. Soc. 2005, 127, 12697
8. MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469
9. Gerkensmeier, T.; Iwanek, W.; Agena, C.; Frohlich, R.; Kotila, S.; Nather, C.; Mattay, J. Eur. J. Org. Chem. 1999, 2257
10. Gonzalez, J. J.; Ferdani, R.; Albertini, E.; Blasco, J. M.; Arduini, A.; Pochini, A.; Prados, P.; de Mendoza, J. Chem.-Eur. J. 2000, 6, 73
11. Kobayashi, K.; Ishii, K.; Sakamoto, S.; Shirasaka, T.; Yamaguchi, K. J. Am. Chem. Soc. 2003, 125, 10615
12. Scarso, A.; Pellizzaro, L.; De Lucchi, O.; Linden, A.; Fabris, F. Angew. Chem., Int. Ed. 2007, 46, 4972
13. Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 509
14. Yoshizawa, M.; Kusukawa, T.; Fujita, M.; Yamaguchi, K. J. Am. Chem. Soc. 2000, 122, 6311
15. Yoshizawa, M.; Tamura, M.; Fujita, M. Science 2006, 312, 251
16. Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2006, 45, 745
17. Fiedler, D.; Leung, D. H.; Bergman, R. G.; Raymond, K. N. Acc. Chem. Res. 2005, 38, 349
18. Ziegler, M.; Brumaghim, J. L.; Raymond, K. N. Angew. Chem., Int. Ed. 2000, 39, 4119
19. Dong, V. M.; Fiedler, D.; Carl, B.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 14464
20. Kaanumalle, L. S.; Gibb, C. L. D.; Gibb, B. C.; Ramamurthy, V. J. Am. Chem. Soc. 2005, 127, 3674
21. Raymond, K. N.; Pluth, M. D.; Fiedler, D.; Mugridge, J. S.; Bergman, R. G. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 10438
22. Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1136
23. Scarso, A.; Shivanyuk, A.; Hayashida, O.; Rebek, J., Jr. J. Am. Chem. Soc. 2003, 125, 6239
24. Palmer, L. C.; Zhao, Y. L.; Houk, K. N.; Rebek, J., Jr. Chem. Commun. 2005, 3667
25. Yoshizawa, M.; Kusukawa, T.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. J. Am. Chem. Soc. 2001, 123, 10454
26. Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50
27. Yoshizawa, M.; Takeyama, Y.; Kusukawa, T.; Fujita, M. Angew. Chem., Int. Ed. 2002, 41, 1347
28. Kaanumalle, L. S.; Gibb, C. L. D.; Gibb, B. C.; Ramamurthy, V. J. Am. Chem. Soc. 2004, 126, 14366
29. Chen, J.; Rebek, J., Jr. Org. Lett. 2002, 4, 327
30. Yoshizawa, M.; Klosterman, J. K.; Fujita, M. Angew. Chem., Int. Ed. 2009, 48, 3418
31. Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2004, 43, 6748
32. Kang, J. M.; Santamaria, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389
33. Murase, T.; Horiuchi, S.; Fujita, M. J. Am. Chem. Soc. 2010, 132, 2866
34. Shivanyuk, A.; Rebek, J., Jr. J. Am. Chem. Soc. 2002, 124, 12074
35. Shivanyuk, A.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2003, 42, 684
36. Ajami, D.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2007, 46, 9283
37. Ajami, D.; Rebek, J., Jr. J. Am. Chem. Soc. 2006, 128, 5314
38. Tiefenbacher, K.; Ajami, D.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2011, 50, 12003
39. Mecozzi, S.; Rebek, J. J., Jr. Chem.-Eur. J 1998, 4, 1016
40. Paliwal, S.; Geib, S.; Wilcox, C. S. J. Am. Chem. Soc. 1994, 116, 4497
41. Hof, F.; Scofield, D. M.; Schweizer, W. B.; Diederich, F. Angew. Chem., Int. Ed. 2004, 43, 5056
42. Mati, I. K.; Cockroft, S. L. Chem. Soc. Rev. 2010, 39, 4195