Synthesis and characterization of a long, rigid photoswitchable cross-linker for promoting peptide and protein conformational change

ChemBioChem

Volumn 9, Issue 13, 2008, Pages 2147-2154

  Zhang, Fuzhong ^a   Sadovski, Oleg ^a   Woolley, G Andrew ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Azobenzenes; Conformation changes; Cross linkers; Photoswitches; Rigidity

Indexed keywords

AZOBENZENE DERIVATIVE; CYSTEINE; PEPTIDE; THIOL;

ALPHA HELIX; ARTICLE; CIS ISOMER; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; ILLUMINATION; IRRADIATION; ISOMERIZATION; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN CROSS LINKING; PROTEIN SYNTHESIS; ROOM TEMPERATURE; STEADY STATE; TRANS ISOMER;

AMINO ACID SEQUENCE; AZO COMPOUNDS; BENZENESULFONATES; CIRCULAR DICHROISM; CROSS-LINKING REAGENTS; DRUG DESIGN; ISOMERISM; LIGHT; MOLECULAR SEQUENCE DATA; PEPTIDES; PHOTOCHEMISTRY; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; SOLVENTS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 54349088033     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200800196     Document Type: Article

References (40)

1. O. Pieroni, A. Fissi, N. Angelini, F. Lenci, Acc. Chem. Res. 2001, 34, 9-17.
2. C. Renner, L. Moroder, ChemBioChem 2006, 7, 868-878.
3. G. A. Woolley, Acc. Chem. Res. 2005, 38, 486-493.
4. M. Bose, D. Groff, J. Xie, E. Brustad, P. G. Schultz, J. Am. Chem. Soc. 2006, 128, 388-389.
5. N. Muranaka, T. Hohsaka, M. Sisido, FEBS Lett. 2002, 510, 10-12.
6. K. Nakayama, M. Endo, T. Majima, Chem. Commun. 2004, 2386-2387.
7. C. Dohno, S. N. Uno, K. Nakatani, J. Am. Chem. Soc. 2007, 129, 11898.
8. X. Liang, N. Takenaka, H. Nishioka, H. Asanuma, Chem. Asian J. 2008, 3, 553-560.
9. Y. Liu, D. Sen, J. Mol. Biol. 2004, 347, 887-892.
10. A. M. Caamaño, M. E. Vázquez, J. Martínez-Costas, L. Castedo, J. L. Mascareñas, Angew. Chem. 2000, 112, 3234-3237; Angew. Chem. Int. Ed. 2000, 39, 3104-3107.
11. L. Guerrero, O. S. Smart, C. J. Weston, D. C. Burns, G. A. Woolley, R. K. Allemann, Angew. Chem. 2005, 117, 7956-7960; Angew. Chem. Int. Ed. 2005, 44, 7778-7782.
12. G. A. Woolley, A. S. Jaikaran, M. Berezovski, J. P. Calarco, S. N. Krylov, O. S. Smart, J. R. Kumita, Biochemistry 2006, 45, 6075-6084.
13. M. Banghart, K. Borges, E. Isacoff, D. Trauner, R. H. Kramer, Nat. Neurosci. 2004, 7, 1381-1386.
14. L. Lien, D. C. J. Jaikaran, Z. Zhang, G. A. Woolley, J. Am. Chem. Soc. 1996, 118, 12222-12223.
15. M. Volgraf, P. Gorostiza, R. Numano, R. H. Kramer, E. Y. Isacoff, D. Trauner, Nat. Chem. Biol. 2006, 2, 47-52.
16. A. Aemissegger, V. Krautler, W. F. van Gunsteren, D. Hilvert, J. Am. Chem. Soc. 2005, 127, 2929-2936.
17. R. F. Standaert, S. B. Park, J. Org. Chem. 2006, 71, 7952-7966.
18. H. Rau in Photochemistry and Photophysics, Vol. II (Ed.: J. F. Rabek), CRC Press, Boca Raton, 1990, pp. 119-141.
19. Z. Zhang, D. C. Burns, J. R. Kumita, O. S. Smart, G. A. Woolley, Bioconjugate Chem. 2003, 14, 824-829.
20. L. Chi, O. Sadovski, G. A. Woolley, Bioconjugate Chem. 2006, 17, 670-676.
21. N. Pozhidaeva, M. E. Cormier, A. Chaudhari, G. A. Woolley, Bioconjugate Chem. 2004, 15, 1297-1303.
22. A. Aemissegger, D. Hilvert, Nat. Protoc. 2007, 2, 161-167.
23. D. C. Burns, D. G. Flint, J. R. Kumita, H. J. Feldman, L. Serrano, Z. Zhang, O. S. Smart, G. A. Woolley, Biochemistry 2004, 43, 15329-15338.
24. U. Kusebauch, S. A. Cadamuro, H. J. Musiol, M. O. Lenz, J. Wachtveitl, L. Moroder, C. Renner, Angew. Chem. 2006, 118, 7170-7173; Angew. Chem. Int. Ed. 2006, 45, 7015-7018.
25. U. Kusebauch, S.A. Cadamuro, H.J. Musiol, L. Moroder, C. Renner, Chem. Eur. J. 2007, 13, 2966-2973.
26. S. B. Park, R. F. Standaert, Bioorg. Med. Chem. 2001, 9, 3215-3223.
27. D. C. Burns, F. Zhang, G. A. Woolley, Nat. Protoc. 2007, 2, 251-258.
28. J. R. Kumita, O. S. Smart, G. A. Woolley, Proc. Natl. Acad. Sci. USA 2000, 97, 3803-3808.
29. M. S. Vollmer, T. D. Clark, C. Steinem, M. R. Ghadiri, Angew. Chem. 1999, 111, 1703-1706; Angew. Chem. Int. Ed. 1999, 38, 1598-1601.
30. N. Pozhidaeva, M.Sc. Thesis, University of Toronto (Canada), 2004, p. 116.
31. P. Ruggli, E. Peyer, Helv. Chim. Acta 1926, 9, 929-950.
32. V. Temkina, G. Yaroshenko, N. Khavchenko, R. Lastovskii, Metody Poluch. Khim. Reakt. Prep. 1969, 20, 24-27.
33. S. Marqusee, V. H. Robbins, R. L. Baldwin, Proc. Natl. Acad. Sci. USA 1989, 86, 5286-5290.
34. G. Merutka, W. Shalongo, E. Stellwagen, Biochemistry 1991, 30, 4245-4248.
35. A. Chakrabartty, T. Kortemme, S. Padmanabhan, R. L. Baldwin, Biochemistry 1993, 32, 5560-5565.
36. N. Nishimura, T. Sueyoshi, H. Yamanaka, E. Imai, S. Yamamoto, S. Hasegawa, Bull. Chem. Soc. Jpn. 1976, 49, 1381-1387.
37. R. J. W. Le Fèvre, J. Northcott, J. Chem. Soc. 1953, 867-870.
38. V. Borisenko, G. A. Woolley, J. Photochem. Photobiol. A 2005, 173, 21-28.
39. T. Sasaki, J. M. Tour, Org. Lett. 2008, 10, 897-900.
40. J. Bredenbeck, J. Helbing, J. R. Kumita, G. A. Woolley, P. Hamm, Proc. Natl. Acad. Sci. USA 2005, 102, 2379-2384.