Hydrogen-bonded self-assembled peptide nanotubes from cystine-based macrocyclic bisureas

Journal of the American Chemical Society

Volumn 121, Issue 26, 1999, Pages 6103-6106

  Ranganathan, Darshan ^a,c   Lakshmi, C ^a,c   Karle, Isabella L ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b NAVAL RESEARCH LABORATORY   (United States)

^c Centre for Advanced Scientific Research   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTINE; DICARBOXYLIC ACID DERIVATIVE; ISOCYANIC ACID DERIVATIVE; OXALIC ACID; SUCCINIC ACID; UREA DERIVATIVE;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGEN BOND; PEPTIDE SYNTHESIS; PROTEIN ASSEMBLY; PROTEIN LIPID INTERACTION; PROTEIN STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033532918     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9903025     Document Type: Article

References (32)

1. Lee, Y.-S.; Yang, J.-Z.; Sisson, T. M.; Frankel, D. A.; Gleeson, J. T.; Aksay, M.; Keller, S. L.; Gruner, S. M.; O'Brien, D. F. J. Am. Chem. Soc. 1995, 117, 5573-5578.
2. Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518.
3. Gattuso, G.; Menzer, S.; Nepogodiev, S. A.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1451-1454.
4. Benner, K.; Klufers, P.; Schumacher, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 743-745.
5. Abrahams, B. F.; Hoskins, B. F.; Michall, D. M.; Robson, R. Nature 1994, 369, 727-729.
6. Venkataraman, D.; Lee, S.; Zhang, J.; Moore, J. S. Nature 1994, 371, 591-593.
7. Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796.
8. Hartgerink, J. D.; Clark, T. D.; Ghadiri, M. R. Chem. Eur. J. 1998, 4, 1367-1372.
9. Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.; Khazanovich, N. Nature 1993, 366, 324-327.
10. Khazanovich, N.; Granja, J. R.; McRee, D. E.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1994, 116, 6011-6012.
11. Ghadiri, M. R.; Granja, J. R.; Buehler, L. Nature 1994, 369, 301-304.
12. Granja, J. R.; Ghadiri, M. R. J. Am. Chem. Soc. 1994, 116, 10785-10786.
13. Ghadiri, M. R.; Kobayashi, K.; Granja, J. R.; Chadha, R. K.; McRee, D. E. Angew. Chem., Int. Ed. Engl. 1995, 34, 93-95.
14. Kobayashi, K.; Granja, J. R.; Ghadiri, M. R. Angew. Chem., Int. Ed. Engl., ibid. 1995, 34, 95-98.
15. Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50.
16. Kim, H. S.; Hartgerink, J. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 4417-4424.
17. Hassall, C. H. In Proceedings of the Third American Peptide Symposium; Meinhoffer, J., Ed.; Ann Arbor Science: Ann Arbor, MI, 1972; pp 153-157.
18. Karle, I. L.; Handa, B. K.; Hassall, C. H. Acta Crystallogr. 1975, B 31, 555-560.
19. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chim. Acta 1997, 80, 173-182.
20. Clark, T. D.; Buchler, L. K.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 651-656.
21. Ranganathan, D.; Haridas, V.; Gilardi, R.; Karle, I. L. J. Am. Chem. Soc. 1998, 120, 10793-10800.
22. Etter, M. C; Urbanczyk-Lipkowska, Z.; Zia-Ebrahimi, M.; Panuto, T. W. J. Am. Chem. Soc. 1990, 112, 8415-8426.
23. Ranganathan, D.; Kurur, S.; Madhusudanan, K. P.; Karle, I. L. Tetrahedron Lett. 1997, 38, 4659-4662.
24. Zhao, X.; Chang, Y. L.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634.
25. Chang, Y. L.; West, M. A.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1993, 115, 991-6000.
26. Nowick, J. S.; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha G.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 89-99
27. For other examples of receptors for dicarboxylic acids, see: Garcia-Tellado, F.; Goswami, S.; Chang, S. K.; Geib, S.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 7393-7394.
28. Hosseini, M. W.; Lehn, J.-M. J. Am. Chem. Soc. 1982, 104, 3525-3527.
29. Lehn, J.-M.; Meric, R.; Vigneron, J. P.; Bkouche-Waksman, I.; Pascard, C. J. Chem. Soc. Chem. Commun. 1991, 62-64.
30. Rack, S. S.; Chaumette, J. L.; Kilburn, J. D.; Langley, G. J.; Webster, M. J. Chem. Soc. Chem. Commun. 1993, 399-401.
31. Ranganathan, D.; Haridas, V.; Karle, I. L. J. Am. Chem. Soc. 1998, 120, 2695-2702.
32. max is the chemical shift when the receptor is entirely bound, [c] is the concentration of the guest or host. (Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072-7080 and references therein).