Modulation of the peptide backbone conformation by the selenoxo photoswitch

Journal of the American Chemical Society

Volumn 132, Issue 22, 2010, Pages 7578-7579

  Huang, Yun ^a   Jahreis, Günther ^a   Lücke, Christian ^a   Wildemann, Dirk ^a   Fischer, Gunter ^a  

^a MAX PLANCK RESEARCH UNIT FOR ENZYMOLOGY OF PROTEIN FOLDING   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMICAL REACTIONS; EXTERNAL SIGNALS; NON EQUILIBRIUM; PEPTIDE BACKBONES; PEPTIDE BONDS; PEPTIDE CHAIN; PHOTOCONTROL; PHOTOSTATIONARY STATE; RE-EQUILIBRATION; TETRA PEPTIDE; UV LIGHT;

CONFORMATIONS; RATE CONSTANTS; SELENIUM;

PEPTIDES;

AMIDE; SELENOXO AMIDE; UNCLASSIFIED DRUG;

ABSORPTION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL INTERACTION; CONFORMATION; PEPTIDE SYNTHESIS; PROTEIN BINDING; PROTEIN STRUCTURE; ULTRAVIOLET RADIATION;

PEPTIDES; PHOTOCHEMICAL PROCESSES; PROTEIN CONFORMATION; SELENIUM COMPOUNDS;

EID: 77953112894     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1019386     Document Type: Article

References (27)

1. Baldwin, R. L. Biophys. Chem. 2002, 101, 203-210
2. Rose, G. D., Fleming, P. J., Banavar, J. R., and Maritan, A. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 16623-15633
3. Yang, X. Y., Wang, M., and Fitzgerald, M. C. Bioorg. Chem. 2004, 32, 438-449
4. Li, Y., Garrell, R. L., and Houk, K. N. J. Am. Chem. Soc. 1991, 113, 5895-5896
5. Holtz, J. S. W., Li, P. S., and Asher, S. A. J. Am. Chem. Soc. 1999, 121, 3762-3766
6. Wang, Y., Purello, R., Georgiou, S., and Spiro, T. G. J. Am. Chem. Soc. 1991, 113, 6368-6377
7. Renner, C., Kusebauch, U., Loweneck, M., Milbradt, A. G., and Moroder, L. J. Pept. Res. 2005, 65, 4-14
8. Bredenbeck, J., Helbing, J., Kumita, J. R., Woolley, G. A., and Hamm, P. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 2379-2384
9. Schrader, T. E., Schreier, W. J., Cordes, T., Koller, F. O., Babitzki, G., Denschlag, R., Renner, C., Loweneckt, M., Dong, S. L., Moroder, L., Tavan, P., and Zinth, W. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 15729-15734
10. Jurt, S., Aemissegger, A., Güntert, P., Zerbe, O., and Hilvert, D. Angew. Chem., Int. Ed. 2005, 45, 6297-6300
11. Frank, R., Jakob, M., Thunecke, F., Fischer, G., and Schutkowski, M. Angew. Chem., Int. Ed. 2000, 39, 1120-1122
12. Zhao, J., Wildemann, D., Jakob, M., Vargas, C., and Schiene-Fischer, C. Chem. Commun. 2003, 2810-2811
13. Zhao, J. Z., Micheau, J. C., Vargas, C., and Schiene-Fischer, C. Chem.-Eur. J. 2004, 10, 6093-6101
14. Satzger, H., Root, C., Gilch, P., Zinth, W., Wildemann, D., and Fischer, G. J. Phys. Chem. B 2005, 109, 4770-4475
15. Helbing, J., Bregy, H., Bredenbeck, J., Pfister, R., Hamm, P., Huber, R., Wachtveitl, J., De Vico, L., and Olivucci, M. J. Am. Chem. Soc. 2004, 126, 8823-8834
16. Wildemann, D., Schiene-Fischer, C., Aumüller, T., Bachmann, A., Kiefhaber, T., Lücke, C., and Fischer, G. J. Am. Chem. Soc. 2007, 129, 4910-4918
17. Huang, Y., Cong, Z. Y., Yang, L. F., and Dong, S. L. J. Pept. Sci. 2008, 14, 1062-1068
18. To stay consistent with the name "thioxo peptides" and to distinguish the common "selenopeptide", which contains selenocysteines, we refer to these compounds as selenoxo peptides.
19. Murai, T. In Chalcogenocarboxylic Acid Derivatives; Kato, S., Ed.; Topics in Current Chemistry, Vol. 251; Springer-Verlag Berlin: Berlin, 2005; pp 247 - 272.
20. Olszewska, T., Pyszno, A., Milewska, M. J., Gdaniec, M., and Polonski, T. Tetrahedron: Asymmetry 2005, 16, 3711-3717
21. Baxter, I., Hill, A. F., Malget, J. M., White, A. J. P., and Williams, D. J. Chem. Commun. 1988, 1190-1191
22. Glendening, E. D. and Hrabal, J. A. J. Am. Chem. Soc. 1997, 119, 12940-12946
23. Niu, S. Q., Li, G. M., Zingaro, R. A., Reibenspies, J. H., and Ichiye, T. Heteroatom Chem. 2002, 13, 380-386
24. Jensen, K. A. Arch. Pharm. Chem. Sci. Ed. 1981, 9, 93-116
25. Lu, K. P., Finn, G., Lee, T. H., and Nicholson, L. K. Nat. Chem. Biol. 2007, 3, 619-629
26. Fischer, G. and Aumüller, T. Rev. Physiol. Biochem. Pharmacol. 2004, 148, 105-150
27. Eckert, B., Martin, A., Balbach, J., and Schmid, F. X. Nat. Struct. Mol. Biol. 2005, 12, 619-623