Helical molecular programming: Folding of oligopyridine-dicarboxamides into molecular single helices

Chemistry - A European Journal

Volumn 7, Issue 13, 2001, Pages 2798-2809

  Berl, Volker ^a,b   Huc, Ivan ^c   Khoury, Richard G ^a   Lehn, Jean Marie ^a  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^c INSTITUT EUROPÉEN DE CHIMIE ET BIOLOGIE   (France)

Author keywords

Conformation analysis; Folding; Helical structures; Hydrogen bonds; Self assembly

Indexed keywords

HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE; ORGANIC SOLVENTS; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

MOLECULAR PROGRAMMING;

MOLECULAR STRUCTURE;

AROMATIC COMPOUND; BIOPOLYMER; CARBONYL DERIVATIVE; PYRIDINE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

BIOPOLYMERS; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRIDINES;

EID: 0035796494     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010702)7:13<2798::AID-CHEM2798>3.0.CO;2-L     Document Type: Article

References (56)

1. a) A. E. Rowan, R. J. M. Nolte, Angew. Chem. 1998, 110, 65;
2. Angew. Chem. Int. Ed. 1998, 37, 63;
3. b) T. Katz, Angew. Chem. 2000, 112, 1997;
4. Angew. Chem. Int. Ed. 2000, 39, 1921.
5. a) Y. Hamuro, J. S. Geib, A. D. Hamilton, J. Am. Chem. Soc. 1997, 119, 10 587;
6. b) Y. Hamuro, J. S. Geib, A. D. Hamilton, Angew. Chem. 1994, 106, 465;
7. Angew. Chem. Int. Ed. Engl. 1994, 33, 446;
8. c) J. Zhu, R. D. Parra, H. Zeng, E. Skrzypczak-Jankun, X. C. Zeng, B. Gong, J. Am. Chem. Soc. 2000, 122, 4219.
9. a) D. Seebach, M. Overhand, F. N. M. Kühnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1996, 79, 913;
10. b) D. Seebach, P. E. Ciceri, M. Overhand, B. Jaun, D. Rigo, L. Oberer, U. Hommel, R. Amstutz, H. Widmer, Helv. Chim. Acta 1996, 79, 2043;
11. c) D. H. Appella, L. A. Christianson, D. A. Klein, M. R. Richards, D. R. Powell, S. H. Gellman, J. Am. Chem. Soc. 1999, 121, 7574.
12. a) G. S. Hanan, J.-M. Lehn, N. Kyritsakas, J. Fischer, J. Chem. Soc. Chem. Commun. 1995, 765;
13. b) D. Bassani, J.-M. Lehn, G. Baum, D. Fenske, Angew. Chem. 1997, 109, 1931;
14. Angew. Chem. Int. Ed. Engl. 1997, 36, 1845;
15. c) D. Bassani, J.-M. Lehn, Bull. Soc. Chim. Fr. 1997, 134, 897;
16. d) M. Ohkita, J.-M. Lehn, G. Baum, D. Fenske, Chem. Eur. J. 1999, 5, 3471.
17. L. A. Cuccia, J.-M. Lehn, J.-C. Homo, M. Schmutz, Angew. Chem. 2000, 112, 239;
18. Angew. Chem. Int. Ed. 2000, 37, 233.
19. F. R. Heirtzler, M. Neuburger, M. Zehnder, E. C. Constable, Liebigs Ann./Recueil 1997, 297.
20. a) A. Tanatani, H. Kagechika, I. Azumaya, R. Fukutomi, Y. Ito, K. Yamaguchi, K. Shudo, Tetrahedron Lett. 1997, 38, 4425;
21. b) R. Fukutomi, A. Tanatani, H. Kakuta, N. Tomioka, A. Itai, Y. Hashimoto, K. Shudo, H. Kagechika, Tetrahedron Lett. 1998, 39, 6475;
22. c) A. Tanatani, K. Yamaguchi, I. Azumaya, R. Fukutomi, K. Shudo, H. Kagechika, J. Am. Chem. Soc. 1998, 120, 6433.
23. K. P. Meurer, F. Vögtle, Top. Curr. Chem. 1985, 127, 1.
24. For representative examples, see: a) M. S. Newman, D. Lednicer, J. Am. Chem. Soc. 1956, 78, 4765;
25. b) R. H. Martin, G. Morren, J. J. Schurter, Tetrahedron Lett. 1969, 42, 3684;
26. c) R. H. Martin, N. Defay, H. P. Figeys, M. Flammang-Barbieux, J. P. Cosyn, M. Gelbcke, J. J. Schurter, Tetrahedron 1969, 25, 4985;
27. d) T. W. Bell, H. Jousselin, J. Am. Chem. Soc. 1991, 113, 6283;
28. e) C. Nuckolls, T. J. Katz, L. Castellanos, J. Am. Chem. Soc. 1996, 118, 3767;
29. f) B. Kiupel, C. Niederalt, M. Nieger, S. Grimme, F. Vögtle, Angew. Chem. 1998, 110, 3206;
30. Angew. Chem. Int. Ed. 1998, 37, 3031.
31. a) Y. Dai, T. J. Katz, D. A. Nichols, Angew. Chem. 1996, 108, 2230;
32. Angew. Chem. Int. Ed. Engl. 1996, 35, 2109;
33. b) R. B. Prince, T. Okada, J. S. Moore, Angew. Chem. 1999, 111, 245;
34. Angew. Chem. Int. Ed. 1999, 38, 233.
35. J. C. Nelson, J. G. Saven, J. S. Moore, P. G. Wolynes, Science 1997, 277, 1793.
36. a) C.-Y. Huang, V. Lynch, E. V. Anslyn, Angew. Chem. 1992, 104, 1259;
37. Angew. Chem. Int. Ed. Engl. 1992, 31, 1244;
38. b) S. J. Geib, C. Vicent, E. Fan, A. D. Hamilton, Angew. Chem. 1993, 105, 83;
39. Angew. Chem. Int. Ed. Engl. 1993, 32, 119;
40. c) I. L. Karle, D. Ranganathan, V. Haridas, J. Am. Chem. Soc. 1997, 119, 2777;
41. d) N. Kimizuka, T. Kawasaki, K. Hirata, T. Kunitake, J. Am. Chem. Soc. 1995, 117, 6360.
42. a) V. Berl, I. Huc, R. G. Khoury, M. J. Krische, J.-M. Lehn, Nature 2000, 407, 720;
43. b) V. Berl, I. Huc, R. G. Khoury, J.-M. Lehn, Chem. Eur. J. 2001, 7, 2810, following paper in the present issue.
44. V. Berl, M. J. Krische, I. Huc, J.-M. Lehn, M. Schmutz, Chem. Eur. J. 2000, 6, 1938.
45. a) F. Mohamadi, N. G. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467;
46. b) S. J. Weiner, P. A. Kollman, D. Case, U. C. Singh, G. Alagona, S. Profeta, P. Weiner, J. Am. Chem. Soc. 1984, 106, 765.
47. S. M. Redmore, C. E. F. Rickard, S. J. Webb, L. J. Wright, Inorg. Chem. 1997, 36, 4743.
48. Y. H. Kim, J. Calabrese, C. McEwen, J. Am. Chem. Soc. 1996, 118, 1545.
49. T. A. Halgren, J. Comput. Chem. 1996, 17, 490.
50. F. Mohamadi, N. G. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440.
51. M. F. van Gunsteren, H. J. C. Berendsen, Mol. Simul. 1988, 1, 173.
52. W. C. Still, A. Tempczyk, R. C. Hawley, T. Hendrickson, J. Am. Chem. Soc. 1990, 112, 6127.
53. K. Motesharei, D. C Myles, J. Am. Chem. Soc. 1998, 120, 7328.
54. For a review of the use of Fmoc protection, see: E. Atherton, R. C. Sheppard, The Fluorenylmethoxycarbonyl Amino Protecting Group, in The Peptides, Vol. 9 (Eds.: S. Udenfriend, J. Meierhofer), Academic Press, Orlando, Florida, 1987, pp. 1-38.
55. T. A. Kelly, D. W. McNeil, Tetrahedron Lett. 1994, 35, 9003.
56. R. S. Lott, V. S. Chauhan, C. H. Stammer, J. Chem. Soc. Chem. Commun. 1979, 495.