A water-soluble azobenzene cross-linker for photocontrol of peptide conformation

Bioconjugate Chemistry

Volumn 14, Issue 4, 2003, Pages 824-829

  Zhang, Zhihua ^a   Burns, Darcy C ^a   Kumita, Janet R ^a   Smart, Oliver S ^b   Woolley, G Andrew ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; PEPTIDES;

CONFORMATIONAL CONTROL; CROSSLINKER; MODEL PEPTIDES; PEPTIDE CONFORMATION; PHOTOCONTROL; PHOTOSWITCH; SIMILAR DEGREE; SYNTHESISED; TO EFFECT; WATERSOLUBLE;

AZOBENZENE;

BENZENE DERIVATIVE; PEPTIDE DERIVATIVE;

ARTICLE; PHOTOCHEMISTRY; PROTEIN CONFORMATION; PROTEIN CROSS LINKING; PROTEIN FUNCTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0037778822     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc0340161     Document Type: Article

References (23)

1. Adams, S. R., and Tsien, R. Y. (1993) Controlling cell chemistry with caged compounds. Annu. Rev. Physiol. 55, 755-784.
2. Curley, K., and Lawrence, D. S. (1999) Light-activated proteins. Curr Opin. Chem. Biol. 3, 84-88.
3. Miller, J. C., Silverman, S. K., England, P. M., Dougherty, D. A., and Lester, H. A. (1998) Flash decaging of tyrosine side chains in an ion channel. Neuron 20, 619-624.
4. Pan, P., and Bayley, H. (1997) Caged cysteine and thiophosphoryl peptides. FEBS Lett. 405, 81-85.
5. Willner, I., and Rubin, I. (1996) Control of the structure and functions of biomaterials by light. Angew. Chem., Int. Ed. Engl. 35, 367-385.
6. Liu, D., Karanicolas, J., Yu, C., Zhang, Z., and Woolley, G. A. (1997) Site-specific incorporation of photoisomerizable azobenzene groups into ribonuclease S. Bioorg. Med. Chem. Lett. 7, 2677-2680.
7. Hamachi, I., Hiraoka, T., Yamada, Y., and Shinkai, S. (1998) Photoswitching of the enzymatic activity of semisynthetic ribonuclease S bearing phenylazophenylalanine at a specific site. Chem. Lett. 6, 537-538.
8. James, D. A., Burns, D. C., and Woolley, G. A. (2001) Kinetic characterization of ribonuclease S mutants containing photoisomerizable phenylazophenylalanine residues. Protein Eng. 14, 983-991.
9. Flint, D. G., Kumita, J. R., Smart, O. S., and Woolley, G. A. (2002) Using an azobenzene cross-linker to either increase or decrease peptide helix content upon trans-to-cis photoisomerization. Chem. Biol. 9, 391-397.
10. Behrendt, R., Renner, C., Schenk, M., Wang, F., Wachtveitl, J., Oesterhelt, D., and Moroder, L. (1999) Photomodulation of the conformation of cyclic peptides with azobenzene moieties in the peptide backbone. Angew. Chem., Int. Ed. 38, 2771-2774.
11. Asanuma, H., Liang, X., Yoshida, T., and Komiyama, M. (2001) Photocontrol of DNA duplex formation by using azobenzene-bearing oligonucleotides. ChemBioChem 2, 39-44.
12. Liang, X., Asanuma, H., and Komiyama, M. (2002) Photoregulation of DNA triplex formation by azobenzene. J. Am. Chem. Soc. 124, 1877-1883.
13. Renner, C., Behrendt, R., Heim, N., and Moroder, L. (2002) Photomodulation of conformational states. III. Water-soluble bis-cysteinyl-peptides with (4-aminomethyl) phenylazobenzoic acid as backbone constituent. Biopolymers 63, 382-393.
14. Wachtveitl, J., Nagele, T., Puell, B., Zinth, W., Kruger, M., Rudolph-Bohner, S., Oesterhelt, D., and Moroder, L. (1997). Ultrafast photoisomerization of azobenzene compounds. J. Photochem. Photobiol. A. Chem. 105, 283-288.
15. Kumita, J. R., Smart, O. S. and Woolley, G. A. (2000) Photocontrol of helix content in a short peptide. Proc. Natl. Acad. Sci. U.S.A. 97, 3803-3808.
16. Kumita, J. R., Flint, D. G., Smart, O. S., and Woolley, G. A. (2002) Photocontrol of peptide helix content by an azobenzene cross-linker: steric interactions with underlying residues are not critical. Protein Eng. 15, 561-569.
17. Fahy, G. M., Lilley, T. H., Linsdell, H., Douglas, M. S., and Meryman, H. T. (1990) Cryoprotectant toxicity and cryoprotectant toxicity reduction: in search of molecular mechanisms. Cryobiology 27, 247-268.
18. Santucci, R., Laurenti, E., Sinibaldi, F., and Ferrari, R. P. (2002) Effect of dimethyl sulfoxide on the structure and the functional properties of horseradish peroxidase as observed by spectroscopy and cyclic voltammetry. Biochim. Biophys. Acta 1596, 225-233.
19. Bhattacharjya, S., and Balaram, P. (1997) Effects of organic solvents on protein structures: observation of a structured helical core in hen egg-white lysozyme in aqueous dimethyl sulfoxide. Proteins 29, 492-507.
20. Hadden, C. E., Martin, G. E., and Krishnamurthy, V. V. (2000) Constant time inverse-detection gradient accordian rescaled heteronuclear multiple bond correlation spectroscopy: CIGAR-HMBC. Magn. Res. Chem. 38, 143-147.
21. Kallenbach, N. R. and Spek, E. J. (1998). Modified amino acids as probes of helix stability. Methods Enzymol. 295, 26-41.
22. Sporlein, S., Carstens, H., Satzger, H., Renner, C., Behrendt, R., Moroder, L., Tavan, P., Zinth, W., and Wachtveitl, J. (2002). Ultrafast spectroscopy reveals subnanosecond peptide conformational dynamics and validates molecular dynamics simulation. Proc. Natl. Acad. Sci. U.S.A 99, 7998-8002.
23. Rau, H. (1990). Photoisomerization of Azobenzenes. In Photochemistry and Photophysics (J. F. Rabek, Ed.), vol. II. pp 119-141, CRC Press Inc., Boca Raton, FL.