Design, synthesis, crystal structure, and host-guest properties of polymethylene-bridged cystine-based cyclobisamides: A facile entry into hydrogen-bonded peptide nanotubes

Journal of Organic Chemistry

Volumn 64, Issue 25, 1999, Pages 9230-9240

  Ranganathan, Darshan ^a   Haridas, V ^a   Sundari, C Sivakama ^c   Balasubramanian, D ^b   Madhusudanan, K P ^d   Roy, Raja ^d   Karle, Isabella L ^e  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b L V PRASAD EYE INSTITUTE   (India)

^c CENTRE FOR CELLULAR AND MOLECULAR BIOLOGY   (India)

^d CENTRAL DRUG RESEARCH INSTITUTE   (India)

^e NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CYCLOBISAMIDE; MELITTIN; POLY(METHYL METHACRYLATE); UNCLASSIFIED DRUG; WATER;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; LIPOPHILICITY; POLYMERIZATION; PROTEIN SECONDARY STRUCTURE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032776268     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991378m     Document Type: Article

References (39)

1. (a) Lijima, S. Nature 1991, 354, 56.
2. (b) Ajayan, P. M.; Ebbeson, T. W. Rep. Prog. Phys. 1997, 60, 1025.
3. (c) Wong, S. S.; Joselevich, E.; Woolley, A. T.; Cheung, C. Li.; Lieber, C. M. Nature 1998, 394, 52.
4. Chopra, N. G.; Luyken, R. J.; Cherry, K., Crespi, V. H.; Cohen, M. L.; Louie, S. G.; Zettl, A. Science 1995, 269, 966.
5. Tenne, F.; Margulis, L.; Genut, M.; Hodes, G. Nature 1992, 360, 444.
6. (a) Meier, W. M.; Olson, D. H. Atlas of Zeolite Structure Types; Butterworths: London, 1988.
7. (b) Dessau, R. M.; Schlenker, J. L.; Higgins, J. B. Zeolites 1990, 10, 522.
8. (c) Munoz, T.; Balkus, K. J., Jr. J. Am. Chem. Soc. 1999, 121, 139.
9. Lee, Y.-S.; Yang, J.-Z.; Sisson, T. M.; Frankel, D. A.; Gleeeson, J. T.; Aksay, M.; Kellar, S. L.; Gruner, S. M.; O'Brien, D. F. J. Am. Chem. Soc. 1995, 117, 5573.
10. (a) Harada, A.; Kamachi, J. Li. M. Nature 1993, 364, 516.
11. (b) Gattuso, G.; Menzer, S.; Nepogodiev, S. A.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1451.
12. (c) Benner, K.; Klufers, P.; Schumacher, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 743.
13. De Santis, P.; Morosetti, S.; Rizzo, R. Macromolecules 1974, 7, 52.
14. (a) Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.; Khazanovich, N. Nature 1993, 366, 324.
15. (b) Ghadiri, M. R.; Granja, J. R.; Buehler, L. K. Nature 1994, 369, 301.
16. (c) Granja, J. R.; Ghadiri, M. R. J. Am. Chem. Soc. 1994, 116, 10785.
17. (d) Khazanovich, N.; Granja, J. R.; McRee, D. E.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1994, 116, 6011.
18. (e) Ghadiri, M. R. Adv. Mater. 1995, 7, 675.
19. (f) Ghadiri, M. R.; Kobyashi, K.; Granja, J. R.; Chadha, R. K.; McRee, D. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 93.
20. (g) Kobyashi, K.; Granja, J. R.; Ghadiri, M. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 95.
21. (h) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364.
22. (i) Engels, M.; Bashford, D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 9151.
23. (j) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43.
24. (k) Motesharei, K.; Ghadiri, M. R. J. Am. Chem. Soc. 1997, 119, 11306.
25. (l) Kim, H. S.; Hartgerink, J. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 4417.
26. (m) Hartgerink, J. D.; Clark, T. D.; Ghadiri, M. R. Chem. Eur. J. 1998, 4, 1367.
27. (a) Hassall, C. H. In Proceedings of the Third American Peptide Symposium; Meinhoffer, J., Ed.; Ann Arbor Science: Ann Arbor, MI, 1972; pp 153-157.
28. (b) Karle, I. L.; Handa, B. K.; Hassall, C. H. Acta Crystallogr. 1975, B31, 555.
29. Seebach, D.; Matthews, J. L.; Meden, A.; Weasels, T.; Baerlocher, C.; McCusker, J. B. Helv. Chim. Acta 1997, 80, 173.
30. Clark, T. D.; Buehler, L. K.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 651.
31. Robertson, J. M.; White, J. G. 1947, 358. (b) Soutar, A. K.; Pownall, H. J.; Hu, S. A. Biochemistry 1974, 13, 2828.
32. 1) is often called the Ham ratio and is used as an indicator of the polarity of the medium in which pyrene is placed, (a) Nakajima, A. Bull. Chem. Soc. Jpn. 1971, 44, 3272. (b) Kalyanasundaram, K.; Thomas, J. K. J. Am. Chem. Soc. 1977, 99, 2039. (c) Dong, D. C.; Winnik, M. A. Photochem. Photobiol. 1982, 35, 17.
33. 1) is often called the Ham ratio and is used as an indicator of the polarity of the medium in which pyrene is placed, (a) Nakajima, A. Bull. Chem. Soc. Jpn. 1971, 44, 3272. (b) Kalyanasundaram, K.; Thomas, J. K. J. Am. Chem. Soc. 1977, 99, 2039. (c) Dong, D. C.; Winnik, M. A. Photochem. Photobiol. 1982, 35, 17.
34. 1) is often called the Ham ratio and is used as an indicator of the polarity of the medium in which pyrene is placed, (a) Nakajima, A. Bull. Chem. Soc. Jpn. 1971, 44, 3272. (b) Kalyanasundaram, K.; Thomas, J. K. J. Am. Chem. Soc. 1977, 99, 2039. (c) Dong, D. C.; Winnik, M. A. Photochem. Photobiol. 1982, 35, 17.
35. Zachariasse, K. A.; Vaz, W. L. C.; Sotomayor, C.; Kuhnle, W. Biochim. Biophys. Acta 1982, 688, 323.
36. Maitra, U.; Rao, P.; Vijay Kumar, P.; Balasubramanian, R.; Mathew, L. Tetrahedron Lett. 1998, 39, 3255.
37. Dimroth K.; Riechardt, C.; Siepmann, T.; Bohlmann F. Liebigs Ann. Chem. 1963, 661, 1.
38. Sarkar, N.; Das, K.; Bhattacharya, K. Langmuir 1994, 10, 326.
39. Chandani, B.; Balasubramanian, D. Biopolymers 1986, 25, 1259.