Simultaneous parallel and antiparallel self-assembly in a triazole/amide macrocycle conformationally homologous to d-, L-α-amino acid based cyclic peptides: NMR and molecular modeling study

Organic Letters

Volumn 13, Issue 20, 2011, Pages 5512-5515

  Ghorai, Abhijit ^a   Gayen, Anindita ^b   Kulsi, Goutam ^a   Padmanaban, E ^a   Laskar, Aparna ^a   Achari, Basudeb ^a   Mukhopadhyay, Chaitali ^b   Chattopadhyay, Partha ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b UNIVERSITY OF CALCUTTA   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID; CYCLOPEPTIDE; MACROCYCLIC COMPOUND; NANOMATERIAL; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMIDES; AMINO ACIDS; CRYSTALLOGRAPHY, X-RAY; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NANOSTRUCTURES; PEPTIDES, CYCLIC; STEREOISOMERISM; TRIAZOLES;

EID: 80054680094     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2022356     Document Type: Article

References (26)

1. Gao, X.; Matsui, H. Adv. Mater. 2005, 17, 2037
2. Ulijn, R. V.; Smith, A. M. Chem. Soc. Rev. 2008, 37, 664
3. Bong, D. T.; Clark, T. D.; Granja, J. R.; Ghadiri, M. R. Angew. Chem. 2001, 113, 1016
4. Angew. Chem., Int. Ed. 2001, 40, 988.
5. Clark, T. D; Buehler, L. K.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 651
6. Ghadiri, M. R.; Kobayashi, K.; Granja, J. R.; Chadha, R. K. Angew. Chem. 1995, 107, 76
7. Clark, T. D.; Kobayashi, J. M.; Isler, M. P.; McRee, D. E.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 8949
8. Seebach, D.; Matthews, J. L.; Meden, A.; Wessels, T.; Baerlocher, C.; McCusker, L. B. Helv. Chim. Acta 1997, 80, 173
9. Gauthier, D.; Baillargeon, P.; Drouin, M.; Dory, Y. L. Angew. Chem. 2001, 113, 4771
10. Baillargeon, P.; Bernard, S; Gauthier, D.; Skouta, R.; Dory, Y. L. Chem.-Eur. J. 2007, 13, 9223
11. Karle, I.; Handa, B. K.; Hassall, C. H. Acta Crystallogr., Sect. B 1975, 31, 555
12. Amorin, M.; Castedo, L.; Granja, J. R. J. Am. Chem. Soc. 2003, 125, 2844
13. Horne, W. S.; Stout, C. D.; Ghadiri, M. R. J. Am. Chem. Soc. 2003, 125, 9372 and references therein
14. (a) Fischer, L.; Decossas, M.; Briand, Jean-Paul.; Didierjean, C.; Guichard., G. Angew. Chem., Int. Ed. 2009, 48, 1625 and references therein
15. Jagannadh, B.; Reddy, M. S.; Lohitha Rao, C.; Prabhakar, A.; Jagadeesh, B.; Chandrasekhar, S. Chem. Commun. 2006, 4847
16. Fujimura, F.; Fukuda, M.; Sugiyama, J.; Morita, T.; Kimura, S. Org. Biomol. Chem. 2006, 4, 1896
17. Angell, Yu L.; Burgess, K. Chem. Soc. Rev. 2007, 36, 1674
18. Angelo, N.; Arora, P. S. J. Am. Chem. Soc. 2005, 127, 17134
19. Brik, A.; Alexandratos, J.; Lin, Y. C.; Elder, J. H.; Olson, A. J.; Wlodawer, A.; Goodsell, D. S.; Wong, C. H. ChemBioChem 2005, 6, 1167
20. Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715
21. Ohira, S. Synth. Commun. 1989, 19, 561
22. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596
23. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057
24. Adhikary, N. D.; Chattopadhyay, P. Eur. J. Org. Chem. 2010, 1754
25. Majhi, T. P.; Neogi, A.; Mukhopadhyay, R.; Chattopadhyay, P. Synthesis 2005, 2307
26. Qu, W; Tan, H; Chen, G; Liu, R. Int. J. Quantum Chem. 2010, 110, 1648