Abstract
Fluorescent peptide substrates of the resonance energy transfer type, employing thedonor–acceptor pair 5-[(2′-aminoethyl)amino]naphthalene sulphonic acid(EDANS) and 4-[[4′-(dimethylamino)phenyl]azo]benzoic acid (DABCYL), are widelyused for continuous monitoring of the activity of various proteases. We describe here aflexible synthetic scheme which allows the synthesis of peptides having EDANS andDABCYL in any position of the sequence; the synthesis is entirely performed on solid phasewith standard methods and makes use only of EDANS, DABCYL and commercially availableamino acid derivatives. Moreover, we show that our scheme can be equally applied to thesynthesis of EDANS/DABCYL-derivatised depsipeptides.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Matayoshi, E.D., Wang, G.T., Krafft, G.A. and Erickson, J., Science, 247 (1990) 954.
Meldal, M. and Breddam, K., Anal. Biochem., 195 (1991) 141.
Wang, G.T. and Krafft, G.A., Bioorg. Med. Chem. Lett., 2 (1992) 1665.
Maggiora, L.L., Smith, C.W. and Zhang, Z.-Y., J. Med. Chem., 35 (1992) 3727.
Wang, G.T., Chung, C.C., Holzman, T.F. and Krafft, G.A., Anal. Biochem., 210 (1993) 351.
Andreae, F., Sommergruber, W., Gauss-Muller, V., Schultheis, T. and Ahorn, H., In Epton, R. (Ed.) Innovation and Perspectives in Solid Phase Synthesis, 3rd International Symposium, Mayflower Worldwide, Birmingham, U.K., 1994, pp. 433–436.
Krafft, G.A. and Wang, G.T., Methods Enzymol., 241 (1994) 70.
Pennington, M.W. and Thornberry, N.A., Pept. Res., 7 (1994) 72.
Holskin, B.P., Bukhtiyarova, M., Dunn, B.M., Baur, P., De Chastonay, J. and Pennington, M.W., Anal. Biochem., 226 (1995) 148.
Pinko, C., Margosiak, S.A., Vanderpool, D., Gutowski, J.C., Condon, B. and Kan, C.-C., J. Biol. Chem., 270 (1995) 23634.
Meldal, M., Svendsen, I., Breddam, K. and Auzanneau, F.-I., Proc. Natl. Acad. Sci. USA, 91 (1994) 3314.
Meldal, M. and Svendsen, I., J. Chem. Soc. Perkin Trans. I, (1995) 1591.
Taliani, M., Bianchi, E., Narjes, F., Fossatelli, M., Urbani, A., Steinkühler, C., De Francesco, R. and Pessi, A., Anal. Biochem., 240 (1996) 60.
Handa, B.K. and Keech, E., Int. J. Pept. Protein Res., 40 (1992) 66.
Atherton, E. and Sheppard, R.C., Solid Phase Peptide Synthesis, IRL Press, Oxford, U.K., 1989, pp. 134–137.
Bianchi, E., Steinkühler, C., Taliani, M., Urbani, A., De Francesco, R. and Pessi, A., Anal. Biochem., 237 (1996) 239.
Albericio, F., Barany, G., Fields, G.B., Hudson, D., Kates, S.A., Lyttle, M.H. and Sole, N.A., In Schneider, C.H. and Eberle, A.N. (Eds.) Peptides 1992 (Proceedings of the 22nd European Peptide Symposium), ESCOM, Leiden, The Netherlands, 1993, pp. 191–193.
Sole, N.A. and Barany, G., J. Org. Chem., 57 (1992) 5399.
Steinkühler, C., Tomei, L. and De Francesco, R., J. Biol. Chem., 271 (1996) 6367.
Cunningham, B.R., Hannah, J. and Jones, A.B., Tetrahedron Lett., 35 (1994) 9517.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Taliani, M., Bianchi, E. & Pessi, A. An improved solid-phase synthesis of resonance energy transfer fluorescent peptides and depsipeptides employing the EDANS/DABCYL donor-acceptor pair. Letters in Peptide Science 4, 101–106 (1997). https://doi.org/10.1023/A:1008850705928
Issue Date:
DOI: https://doi.org/10.1023/A:1008850705928