A single α-helical turn stabilized by replacement of an internal hydrogen bond with a covalent ethylene bridge

Angewandte Chemie - International Edition

Volumn 48, Issue 31, 2009, Pages 5675-5678

  Vernall, Andrea J ^a   Cassidy, Peter ^a   Alewood, Paul F ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Covalent bridging; Helical structures; Hydrogen bonds; Peptidomimetics

Indexed keywords

CARBON BRIDGE; CD SPECTRA; COVALENT BRIDGING; ETHYLENE LINKAGE; HELICAL STRUCTURES; INTERNAL HYDROGEN BONDS; MIMETICS; PEPTIDOMIMETICS; SMALLEST UNIT;

AMINES; BINDING SITES; ETHYLENE; HYDROGEN;

HYDROGEN BONDS;

ETHYLENE; ETHYLENE DERIVATIVE; PEPTIDE;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; HYDROGEN BOND; PROTEIN SECONDARY STRUCTURE; SYNTHESIS;

CIRCULAR DICHROISM; ETHYLENES; HYDROGEN BONDING; PEPTIDES; PROTEIN STRUCTURE, SECONDARY;

EID: 70349931770     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901059     Document Type: Article

References (30)

1. F. Schumann, A. Mueller, M. Koksch, G. Mueller, N. Sewald, J. Am. Chem. Soc. 2000, 122, 12009.
2. I. Chatterjee, C. Gilon, A. Hoffman, H. Kessler, Acc. Chem. Res. 2008, 41, 1331.
3. I A. Robinson, Acc. Chem. Res. 2008, 41, 1278.
4. R. Chapman, I L. I. Kulp, A. Patgiri, N. R. Kallenbach, C. Bracken, P. S. Arora, Biochemistry 2008, 47, 4189.
5. P. H. Kussie, S. Gorina, V. Marechal, B. Elenbaas, J. Moreau, A. J. Levine, N. P. Pavletich, Science 1996, 274, 948.
6. B. H. Zimm, J. K. Bragg, J. Chem. Phys. 1959, 31, 526.
7. L. K. Henchey, A. L. Jochim, P. S. Arora, Curr. Opin. Chem. Biol. 2008, 12, 692.
8. K. A. Carpenter, R. Schmidt, S. Y. Yue, L. Hodzic, C. Pou, K. Payza, C. Godbout, W. Brown, E. Roberts, Biochemistry 1999, 38, 15295.
9. N. E. Shepherd, G. Abbenante, D. P. Fairlie, Angew. Chem. 2004, 116, 2741;
10. Angew. Chem. Int. Ed. 2004, 43, 2687.
11. C. E. Schafmeister, J. Po, G. L. Verdine, J. Am. Chem. Soc. 2000, 122, 5891.
12. H. E. Blackwell, J. D. Sadowsky, R. J. Howard, J. N. Sampson, J. A. Chao, W. E. Steinmetz, D. J. O'Leary, R. H. Grubbs, J. Org. Chem. 2001, 66, 5291.
13. M. I Kelso, R. L. Beyer, H. N. Hoang, A. S. Lakdawala, J. P. Snyder, W. V. Oliver, T. A. Robertson, T. G. Appleton, D. P. Fairlie, J. Am. Chem. Soc. 2004, 126, 4828.
14. I. L. Karle, P. Balaram, Biochemistry 1990, 29, 6747.
15. B. Vaz, L. Brunsveld, Org. Biomol. Chem. 2008, 6, 2988.
16. A. Lewis, T. I Rutherford, J. Wilkie, T. Jenn, D. Gani, J. Chem. Soc. Perkin Trans. 1 1998, 3795.
17. P. Maity, B. Knig, Org. Lett. 2008, 10, 1473.
18. I M. Davis, A. Truong, A. D. Hamilton, Org. Lett. 2005, 7, 5405.
19. E. Cabezas, A. C. Satterthwait, J. Am. Chem. Soc. 1999, 121, 3862.
20. R. N. Chapman, G. Dimartino, P. S. Arora, J. Am. Chem. Soc. 2004, 126, 12252.
21. D. Wang, W. Liao, P. S. Arora, Angew. Chem. 2005, 117, 6683;
22. Angew. Chem. Int. Ed. 2005, 44, 6525.
23. J. Yang, K. Zhao, Y. Gong, A. Vologodskii, N. R. Kallenbach, J. Am. Chem. Soc. 1998, 120, 10646.
24. K. Mitsukawa, X. Lu, T. Bartfai, Cell. Mol. Life Sci. 2008, 65, 1796.
25. M. B. Morris, G. B. Ralston, T. I Biden, C. L. Browne, G. F. King, T. P. Iismaa, Biochemistry 1995, 34, 4538.
26. W. Wiczk, P. Rekowski, G. Kupryszewski, J. Lubkowski, S. Oldziej, A. Liwo, Biophys. Chem. 1996, 58, 303.
27. R. Mandel, G. Holzwarth, Biophys. Chem. 1972, 57, 3469.
28. D. S. Wishart, C. G. Bigam, A. Holm, R. S. Hodges, B. D. Sykes, J. Biomol. NMR 1995, 5, 67.
29. P. Luo, R. L. Baldwin, Biochemistry 1997, 36, 8413.
30. A. Öhman, R. Davydov, B. Backlund, U. Langel, A. Gräslund, Biophys. Chem. 1996, 59, 185.