Development of a series of cross-linking agents that effectively stabilize α-helical structures in various short peptides

Chemistry - A European Journal

Volumn 14, Issue 3, 2008, Pages 857-863

  Fujimoto, Kazuhisa ^a   Kajino, Masaoki ^a   Inouye, Masahiko ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Alpha helices; Cross linking agents; Helical structures; Peptides

Indexed keywords

CROSSLINKING; DICHROISM; SYNTHESIS (CHEMICAL);

ALPHA HELICES; CROSSLINKING AGENTS; HELICAL STRUCTURES;

PEPTIDES;

CROSS LINKING REAGENT; PEPTIDE;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; DRUG EFFECT; ISOLATION AND PURIFICATION; PROTEIN SECONDARY STRUCTURE; SYNTHESIS;

CIRCULAR DICHROISM; CROSS-LINKING REAGENTS; MOLECULAR CONFORMATION; PEPTIDES; PROTEIN STRUCTURE, SECONDARY;

EID: 38849169899     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700843     Document Type: Article

References (32)

1. Recent reviews: a) N. Errington, T. Iqbalsyah, A. J. Doig, In Protein Design: Methods and Applications (Methods in Molecular Biology) (Eds.: R. Guerois, M. Lopez De La Paz), Humana Press, Totowa, 2006, pp. 3-26;
2. b) A. J. Doig, N. Errington, T. Iqbalsyah, In Protein Folding Handbook, Vol. 1 (Eds. : J. Buchner, T. Kiefhaber), Wiley-VCH, Weinheim, 2005, pp. 247-313;
3. c) G. Licini, L. J. Prins, P. Scrimin, Eur. J. Org. Chem. 2005, 969-977.
4. a) D. Wang, K. Chen, J. L. Kulp, III, P. S. Arora, J. Am. Chem. Soc. 2006, 128, 9248-9256;
5. b) D. Wang, W. Liao, P. S. Arora, Angew. Chem. 2005, 117, 6683-6687;
6. Angew. Chem. Int. Ed. 2005, 44, 6525-6529;
7. c) R. N. Chapman, G. Dimartino, P. S. Arora, J. Am. Chem. Soc. 2004, 126, 12252-12253.
8. a) S. Hyun, H. J. Kim, N. J. Lee, K. H. Lee, Y. Lee, D. R. Ahn, K. Kim, S. Jeong, J. Yu, J.. Am. Chem. Soc. 2007, 129, 4514-4515;
9. b) M. Bellanda, S. Mammi, S. Geremia, N. Demitri, L. Randaccio, Q. B. Broxterman, B. Kaptein, P. Pengo, L. Pasquato, P. Scrimin, Chem. Eur. J. 2007, 13, 407-416;
10. c) A. Barazza, A. Wittelsberger, N. Fiori, E. Schievano, S. Mammi, C. Toniolo, J. M. Alexander, M. Rosenblatt, E. Peggion, M. Chorev, J. Pept. Res. 2005, 65, 23-35.
11. a) J. C. Lin, B. Barua, N. H. Andersen, J. Am. Chem. Soc. 2004, 126, 13679-13684;
12. b) J. W. Neidigh, R. M. Fesinmeyer, N. H. Andersen, Nat. Struct. Biol. 2002, 9, 425-430.
13. a) N. L. Mills, M. D. Daugherty, A. D. Frankel, R. K. Guy, J. Am. Chem. Soc. 2006, 128, 3496-3497;
14. b) G. A. Woolley, Acc. Chem. Res. 2005, 38, 486-493;
15. c) D. J. Cline, C. Thorpe, J. P. Schneider, J. Am. Chem. Soc. 2003, 125, 2923-2929;
16. d) C. E. Schafmeister, J. Po, G. L. Verdine, J. Am. Chem. Soc. 2000, 122, 5891-5892.
17. K. Fujimoto, N. Oimoto, K. Katsuno, M. Inouye, Chem. Commun. 2004, 1280-1281.
18. a) A. K. Sato, M. Viswanathan, R. B. Kent, C. R. Wood, Curt. Opin. Biotechnol. 2006, 17, 638-642;
19. b) D. J. Barlow, In Smith and Williams' Introduction to the Principles of Drug Design and Action (Ed.: H. J. Smith), CRC Press, Boca Raton, 4th ed., 2006, pp. 327-354;
20. c) J. A. Kritzer, O. M. Stephens, D. A. Guarracino, S. K. Reznik, A. Schepartz, Bioorg. Med. Chem. 2005, 13, 11-16.
21. a) M. L. Zapp, M. R. Green, Nature 1989, 342, 714-716;
22. b) T. J. Daly, K. S. Cook, G. S. Gray, T. E. Maione, J. R. Rusche, Nature 1989, 342, 816-819.
23. Recent papers for Rev-RRE interactions: See refs. [1c, 4a].
24. K. Fujimoto, M. Amano, Y. Horibe, M. Inouye, Org. Lett. 2006, 8, 285-287.
25. J. L. Battiste, H. Mao, N. S. Rao, R. Tan, D. R. Muhandiram, L. E. Kay, A. D. Frankel, J. R. Williamson, Science 1996, 273, 1547-1551.
26. A reference paper for the sequence of peptide D : R. Tan, A. D. Frankel, Proc. Natl. Acad. Sci. USA 1998, 95, 4247-4252.
27. Since the cross-liking agents 7-12 include the fluorescent cores, we measured the fluorescence spectra of the peptides C cross-linked with 7-12. Figure S24 in the Supporting Information shows the excitation and emission spectra of cross-linked C·12 with X=Lys as representative.
28. R. J. Bergeron, G. W. Yao, G. W. Erdos, S. Milstein, F. Gao, W. R. Weimer, O. Phanstiel IV, J. Am. Chem. Soc. 1995, 117, 6658-6665.
29. O. Safarowsky, E. Vogel, F. Vögtle, Eur. J. Org. Chem. 2000, 499-505.
30. Q. Chen, D. A. Sowa, J. Cai, R. Gabathuler, Synth. Commun. 2003, 53, 2401-2421.
31. S. M. Langenegger, R. Häner, Helv. Chim. Acta 2002, 85, 3414-3421.
32. M. Dotrong, R. C. Evers, Polym. Mater. Sci. Eng. 1989, 60, 507-511.