Peptide tertiary structure nucleation by side-chain crosslinking with metal complexation and double "Click" cycloaddition

ChemBioChem

Volumn 9, Issue 11, 2008, Pages 1701-1705

  Torres, Oscar ^a   Yüksel, Deniz ^b   Bernardina, Matt ^a   Kumar, Krishna ^b   Bong, Dennis ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b TUFTS UNIVERSITY   (United States)

Author keywords

Click chemistry; Cycloadditions; Folding; Molecular recognition; Nickel; Peptides

Indexed keywords

COPPER; METAL; PEPTIDE;

ARTICLE; CATALYSIS; CIRCULAR DICHROISM; COMPLEX FORMATION; CONJUGATION; CYCLIZATION; CYCLOADDITION; DIMERIZATION; HYDROPHOBICITY; MASS SPECTROMETRY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN CROSS LINKING; PROTEIN FUNCTION; PROTEIN SECONDARY STRUCTURE; PROTEIN TERTIARY STRUCTURE; ULTRACENTRIFUGATION;

AMINO ACID SEQUENCE; CROSS-LINKING REAGENTS; METALS; MOLECULAR SEQUENCE DATA; NICKEL; PEPTIDES; PROTEIN DENATURATION; PROTEIN FOLDING; PROTEIN STRUCTURE, SECONDARY; PROTEIN STRUCTURE, TERTIARY; TANDEM MASS SPECTROMETRY;

EID: 54349123364     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200800040     Document Type: Article

References (29)

1. a) F. Bernal, A. F. Tyler, S. J. Korsmeyer, L. D. Walensky, G. L. Verdine, J. Am. Chem. Soc. 2007, 129, 2456;
2. b) L. D. Walensky, K. Pitter, J. Morash, K. J. Oh, S. Barbuto, J. Fisher, E. Smith, G. L. Verdine, S. J. Korsmeyer, Mol. Cell 2006, 24, 199;
3. c) D. Wang, W. Liao, P. S. Arora, Angew. Chem. 2005, 117, 6683; Angew. Chem. Int. Ed. 2005, 44, 6525;
4. d) L. D. Walensky, A. L. Kung, I. Escher, T. J. Malia, S. Barbuto, R. D. Wright, G. Wagner, G. L. Verdine, S. J. Korsmeyer, Science 2004, 305, 1466.
5. C. E. Schafmeister, J. Po, G. L. Verdine, J. Am. Chem. Soc. 2000, 122, 5891.
6. M. J. I. Andrews, A. B. Tabor, Tetrahedron 1999, 55, 11711.
7. M. R. Ghadiri, C. Choi, J. Am. Chem. Soc. 1990, 112, 1630.
8. R. N. Chapman, G. Dimartino, P. S. Arora, J. Am. Chem. Soc. 2004, 126, 12252.
9. E. Cabezas, A. C. Satterthwait, J. Am. Chem. Soc. 1999, 121, 3862.
10. a) S. Lifson, A. Roig, J. Chem. Phys. 1961, 34, 1963;
11. b) B. H. Zimm, J. K. Bragg, J. Chem. Phys. 1959, 31, 526.
12. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708; Angew. Chem. Int. Ed. 2002, 41, 2596.
13. a) W. S. Horne, M. K. Yadav, C. D. Stout, M. R. Ghadiri, J. Am. Chem. Soc. 2004, 126, 15366;
14. b) J. H. van Maarseveen, W. S. Horne, M. R. Ghadiri, Org. Lett. 2005, 7, 4503.
15. a) V. D. Bock, R. Perciaccante, T. P. Jansen, H. Hiemstra, J. H. van Maarseveen, Org. Lett. 2006, 8, 919;
16. b) V. Goncalves, B. Gautier, A. Regazzetti, P. Coric, S. Bouaziz, C. Garbay, M. Vidal, N. Inguimbert, Bioorg. Med. Chem. Lett. 2007, 17, 5590;
17. c) H. Jang, A. Fafarman, J. M. Holub, K. Kirshenbaum, Org Lett. 2005, 7, 1951;
18. d) H. Lin, C. T. Walsh, J. Am. Chem. Soc. 2004, 126, 13998;
19. e) S. Punna, J. Kuzelka, Q. Wang, M. G. Finn, Angew. Chem. 2005, 117, 2255; Angew. Chem. Int. Ed. 2005, 44, 2215.
20. a) H. E. Blackwell, R. H. Grubbs, Angew. Chem. 1998, 110, 3469; Angew. Chem. Int. Ed. 1998, 37, 3281;
21. b) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364.
22. a) P. B. Harbury, T. Zhang, P. S. Kim, T. Alber, Science 1993, 262, 1401;
23. b) E. K. O'Shea, J. D. Klemm, P. S. Kim, T. Alber, Science 1991, 254, 539.
24. M. R. Ghadiri, A. K. Fernholz, J. Am. Chem. Soc. 1990, 112, 9633.
25. A. J. Link, M. K. Vink, D. A. Tirrell, J. Am. Chem. Soc. 2004, 126, 10598.
26. K. Oh, Z. Guan, Chem. Commun. 2006, 3069.
27. W. G. Lewis, F. G. Magallon, V. V. Fokin, M. G. Finn, J. Am. Chem. Soc. 2004, 126, 9152.
28. M. O. Steinmetz, I. Jelesarov, W. M. Matousek, S. Honnappa, W. Jahnke, J. H. Missimer, S. Frank, A. T. Alexandrescu, R. A. Kammerer, Proc. Natl. Acad. Sci. USA 2007, 104, 7062.
29. R. Langer, D. A. Tirrell, Nature 2004, 428, 487.