Efficient macrocyclization of preorganized palindromic oligosquaramides

Angewandte Chemie - International Edition

Volumn 45, Issue 41, 2006, Pages 6844-6848

  Rotger, Carmen ^a   Piña, M Neus ^a   Vega, Manuel ^a   Ballester, Pablo ^b   Deyà, Pere M ^a   Costa, Antoni ^a  

^a UNIVERSITAT DE LES ILLES BALEARS   (Spain)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

Foldamers; Hydrogen bonds; Macrocyclization; Squaramides

Indexed keywords

HYDROGEN BONDS; MOLECULAR STRUCTURE; SOLVENTS;

FOLDAMERS; MACROCYCLIZATION; PROTIC SOLVENTS; SQUARAMIDES;

NITROGEN COMPOUNDS;

MACROCYCLIC COMPOUND; PEPTIDE;

ARTICLE; CHEMISTRY; PROTEIN CONFORMATION; PROTEIN FOLDING;

MACROCYCLIC COMPOUNDS; PEPTIDES; PROTEIN CONFORMATION; PROTEIN FOLDING;

EID: 33750489401     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602790     Document Type: Article

References (20)

1. D. J. Craik, Science 2006, 311, 1563-1564.
2. R. J. Clark, H. Fischer, L. Dempster, N. L. Daly, K. J. Rosengren, S. T. Nevin, F. A. Meunier, D. J. Adams, D. J. Craik, Proc. Natl. Acad. Sci. USA 2005, 102, 13 767-13 772.
3. J. Blankenstein, J. Zhu, Eur. J. Org. Chem. 2005, 1949-1964.
4. a) J. C. Wu, N. Tang, W. S. Liu, M. Y. Tan, A. S. C. Chan, Chin. Chem. Lett. 2001, 12, 757-760;
5. b) M. Bru, I. Alfonso, M. I. Burguete, S. V. Luis, Tetrahedron Lett. 2005, 46, 7781-7785.
6. a) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219-3232;
7. b) J. D. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893-4011.
8. L. Yuan, A. R. Sanford, W. Feng, A. Zhang, J. Zhu, H. Zeng, K. Yamato. M. Li, J. S. Ferguson, B. Gong, J. Org. Chem. 2005, 70, 10 660-10 669.
9. a) P. S. Corbin, S. C. Zimmerman, J. Am. Chem. Soc. 2000, 122, 3779-3780;
10. b) P. S. Corbin, S. C. Zimmerman, P. A. Thiessen, N. A. Hawryluk, T. J. Murray, J. Am. Chem. Soc. 2001, 123, 10 475-10 488.
11. J. Garric, J.-M. Léger, A. Grelard, M. Ohkita, I. Huc, Tetrahedron Lett. 2003, 44, 1421-1424.
12. H. S. Gellman, Acc. Chem. Res. 1998, 31, 173-180.
13. M. C. Rotger, M. N. Piña, A. Frontera, G. Martorell, P. Ballester, P. M. Deyà, A. Costa, J. Org. Chem. 2004, 69, 2302-2308.
14. Experimental details regarding the synthesis and characterization of the squaramide compounds are available in the Supporting Information.
15. N. H. Andersen, J. W. Neidigh, S. M. Harris, G. M. Lee, Z. Liu, T. Tong, J. Am. Chem. Soc. 1997, 119, 8547-8561.
16. E. R. Gillies, C. Dolain, J.-M. Léger, I. Huc, J. Org. Chem. 2006, in press.
17. K. Kirshenbaum, A. E. Barrow, R. A. Goldsmith, P. Armand, E. K. Bradley, K. T. V. Truong, K. A. Dill, F. E. Cohen, R. N. Zuckermann, Proc. NatL Acad. Sci. USA 1998, 95, 4303-4308.
18. R. M. Fesinmeyer, F. M. Hudson, N. H. Andersen, J. Am. Chem. Soc. 2004, 126, 7238-7243.
19. L. Yuan, W. Feng, K. Yamato, A. R. Sanford, D. Xu, H. Guo, B. Gong, J. Am. Chem. Soc. 2004, 126, 11 120-11 121.
20. 3 and protic solvents.