Improving foldamer synthesis through protecting group induced unfolding of aromatic oligoamides

Organic Letters

Volumn 8, Issue 22, 2006, Pages 5117-5120

  Zhang, Aimin ^a   Ferguson, Joseph S ^a   Yamato, Kazuhiro ^a   Zheng, Chong ^b   Gong, Bing ^a  

^a UNIVERSITY AT BUFFALO   (United States)

^b NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750904422     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062103d     Document Type: Article

References (22)

1. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015.
2. Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
3. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
4. Cubberley, M. S.; Iverson, B. L. Curr. Opin. Chem. Biol. 2001, 5, 650.
5. Gong, B. Chem.-Eur. J. 2001, 7, 4336.
6. Sanford, A.; Gong, B. Curr. Org. Chem. 2003, 7, 1649.
7. Huc, I. Eur. J. Org. Chem. 2004, 17.
8. Sanford, A.; Yamato, K.; Yang, X. W.; Yuan, L. H.; Han, Y. H.; Gong, B. Eur. J. Biochem. 2004, 271, 1416.
9. Zhu, J.; Parra, R. D.; Zeng, H.; Skrzypczak-Jankun, E.; Zeng, X. C.; Gong, B. J. Am. Chem. Soc. 2000, 122, 4219.
10. Gong, B.; Zeng, H. Q.; Zhu, J.; Yuan, L. H.; Han, Y. H.; Cheng, S. Z.; Furukawa, M.; Parra, R. D.; Kovalevsky, A. Y.; Mills, J. L.; Skrzypczak-Jankun, E.; Martinovic, S.; Smith, R. D.; Zheng, C.; Szyperski, T.; Zeng, X. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11583.
11. Yuan, L.; Zeng, H.; Yamato, K.; Sanford, A. R.; Feng, W.; Atreya, H. S.; Sukumaran, D. K.; Szyperski, T.; Gong, B. J. Am. Chem. Soc. 2004, 126, 16528.
12. Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1997, 119, 10587.
13. Berl, V.; Khoury, R. G.; Huc, I.; Krische, M. J.; Lehn, J.-M. Nature 2000, 407, 720.
14. Dolain, C.; Jiang, H.; Leger, J. M.; Guionneau, P.; Huc, I. J. Am. Chem. Soc. 2005, 127, 12943.
15. Hou, J. L.; Shao, X. B.; Chen, G. J.; Zhou, Y. X.; Jiang, X. K.; Li, Z. T. J. Am. Chem. Soc. 2004, 126, 12386.
16. Parra, R. D.; Zeng, H. Q.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4352.
17. Examples of foldamers containing hydrophobic cavities: (a) Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793.
18. (b) Cuccia, L. A.; Lehn, J. M.; Homo, J. C.; Schmutz, M. Angew. Chem., Int. Ed. 2000, 39, 233.
19. Yuan, L. H.; Sanford, A. R.; Feng, W.; Zhang, A. M.; Zhu, J.; Zeng, H. Q.; Yamato, K.; Li, M. F.; Ferguson, J. S.; Gong, B. J. Org. Chem. 2005, 70, 10660.
20. N-Substitution of a secondary amide by the 2,4-DMB group was reported to induce a conformational change that promoted ring-closing metathesis. See: Creighton, C. J.; Reitz, A. B. Org. Lett. 2001, 3, 893.
21. See Supporting Information for details.
22. Yuan, L. H.; Feng, W.; Yamato, K.; Sanford, A. R.; Xu, D. G.; Guo, H.; Gong, B. J. Am. Chem. Soc. 2004, 126, 11120.