A new motif in the formation of peptide nanotubes: The crystallographic signature

Organic Letters

Volumn 6, Issue 24, 2004, Pages 4463-4465

  Ray, Sudipta ^a   Haldar, Debasish ^a   Drew, Michael G B ^b   Banerjee, Arindam ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

^b UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; ORGANIC COMPOUND; ORGANIC SOLVENT; PEPTIDE NANOTUBE; TYROSINE;

ARTICLE; COVALENT BOND; CRYSTAL; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; HYDROGEN BOND; HYDROPHILICITY; MOLECULAR INTERACTION; MOLECULE; ORGANIC CHEMISTRY;

CRYSTALLIZATION; HYDROGEN BONDING; NANOTUBES; OLIGOPEPTIDES; TYROSINE;

EID: 10044265404     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048253a     Document Type: Article

References (27)

1. (a) Hartgerink, J. D.; Clark, T. D.; Ghadiri, M. R. Chem Eur. J. 1998, 4, 1367-1372.
2. (b) Ranganathan, D. Acc. Chem. Res. 2001, 43, 919-930.
3. (c) Haldar, D.; Banerjee, A.; Drew, M. G. B.; Das, A. K.; Banerjee, A. Chem. Commun. 2003, 1406-1407.
4. Granja, J. R.; Ghadiri, M. R. J. Am. Chem. Soc. 1994, 116, 10785-10786.
5. (a) Clark, T. D.; Buehler, L. K.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 651-656.
6. (b) Sanchez-Ouesada, J.; Isler, M. P.; Ghadiri, M. R. J. Am. Chem. Soc. 2002, 124, 10004-10005.
7. Fernandez-Lopez, S.; Kim, H.-S.; Choi, E. C.; Delgado, M.; Granja, J. R.; Khasanov, A.; Kraehenbuehl, K.; Long, G.; Weinberger, D. A.; Wilcoxen, K. M.; Ghadiri, M. R. Nature 2001, 412, 452-455.
8. Semetey, V.; Didierjean, C.; Briand, J. P.; Aubry, A.; Guichard, G. Angew. Chem., Int. Ed. 2002, 41, 1895-1898.
9. (a) Bong, D. T.; Clark, T. D.; Grangja, J. R.; Ghadiri, M. R. Angew. Chem., Int. Ed. 2001, 40, 988-1011.
10. (b) Hartjerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 8, 43-50.
11. (c) Gauthier, D.; Baillargeon, P.; Drouin, M.; Dory, Y. L. Angew. Chem., Int. Ed. 2001, 40, 4635-4638.
12. (d) Amorín, M.; Castedo, L.; Granja, J. R. J. Am. Chem. Soc. 2003, 125, 2844-2845.
13. (e) Rosenthal-Aizman, K.; Svensson, G.; Unden, A. J. Am. Chem. Soc. 2004, 126, 3372-3373.
14. Karus, T.; Buděšínský, M.; Císářova, I.; Závada, J. Angew. Chem., Int. Ed. 2002, 41, 1715-1717.
15. Seela, F.; Wiglenda, T.; Rosemeyer, H.; Eickmeier, H.; Reuter, H. Angew. Chem., Int. Ed. 2002, 41, 603-604.
16. (a) Fenniri, H.; Mathivanan, P.; Vidale, K. L.; Sherman, D. M.; Hallenga, K.; Wood, K. V.; Stowell, J. G. J. Am. Chem. Soc. 2001, 123, 3854-3855.
17. (b) Fenniri, H.; Deng, B.; Ribbe, A. E. J. Am. Chem. Soc. 2002, 124, 11064-11072.
18. (c) Fenniri, H.; Deng, B.; Ribbe, A. E.; Hallenga, K.; Jacob, J.; Thiyagarajan, P. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 6487-6492.
19. (a) Görbitz, C. H. Chem. Eur. J. 2001, 7, 5153-5159.
20. (b) Vauthey, S.; Santoso, S.; Gong, H.; Watson, N.; Zhang, S. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5355-5360.
21. (c) Reches, M.; Ghazit, E. Science 2003, 300, 625-627.
22. (d) Song, Y.; Challa, S. R.; Medforth, C. J.; Qiu, Y.; Watt, R. K.; Peña, D.; Miller, J.; Swol, E. F. V.; Shelnutt, J. A. Chem. Commun. 2004, 1044-1045.
23. Bodanszky, M.; Bodanszky, A. The Practice of Peptide Synthesis; Springer-Verlag: New York, 1984; pp 1-282.
24. 15 The final R values were R1 0.0776, 0.0677 and wR2 0.1603, 0.1809 for 4169, 4578 data with 7 > 2σ(I) for peptides 1 and 2, respectively. The data have been deposited at the Cambridge Crystallographic Data Center with reference number CCDC 242896.
25. Kabsch, W. J. Appl. Crystallogr. 1988, 21, 916-924.
26. Sheldrick, G. M. Acta Crystallogr. A 1990, 46, 467-473.
27. Sheldrick, G. M. Program for Crystal Structure Refinement; University of Gottingen: Gottingen, 1993.