Skip to main content
Log in

An improved solid-phase synthesis of resonance energy transfer fluorescent peptides and depsipeptides employing the EDANS/DABCYL donor-acceptor pair

  • Published:
Letters in Peptide Science Aims and scope Submit manuscript

Summary

Fluorescent peptide substrates of the resonance energy transfer type, employing the donor-acceptor pair 5-[(2′-aminoethyl)amino]naphthalene sulphonic acid (EDANS) and 4-[[4′-(dimethylamino)phenyl]azo]benzoic acid (DABCYL), are widely used for continuous monitoring of the activity of various proteases. We describe here a flexible synthetic scheme which allows the synthesis of peptides having EDANS and DABCYL in any position of the sequence; the synthesis is entirely performed on solid phase with standard methods and makes use only of EDANS, DABCYL and commercially available amino acid derivatives. Moreover, we show that our scheme can be equally applied to the synthesis of EDANS/DABCYL-derivatised depsipeptides.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Matayoshi, E.D., Wang, G.T., Krafft, G.A. and Erickson, J., Science, 247 (1990) 954.

    PubMed  CAS  Google Scholar 

  2. Meldal, M. and Breddam, K., Anal. Biochem., 195 (1991) 141.

    Article  PubMed  CAS  Google Scholar 

  3. Wang, G.T. and Krafft, G.A., Bioorg. Med. Chem. Lett., 2 (1992) 1665.

    Article  CAS  Google Scholar 

  4. Maggiora, L.L., Smith, C.W. and Zhang, Z.-Y., J. Med. Chem., 35 (1992) 3727.

    Article  PubMed  CAS  Google Scholar 

  5. Wang, G.T., Chung, C.C., Holzman, T.F. and Krafft, G.A., Anal. Biochem., 210 (1993) 351.

    Article  PubMed  CAS  Google Scholar 

  6. 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.

  7. Krafft, G.A. and Wang, G.T., Methods Enzymol., 241 (1994) 70.

    Article  PubMed  CAS  Google Scholar 

  8. Pennington, M.W. and Thornberry, N.A., Pept. Res., 7 (1994) 72.

    PubMed  CAS  Google Scholar 

  9. Holskin, B.P., Bukhtiyarova, M., Dunn, B.M., Baur, P., De Chastonay, J. and Pennington, M.W., Anal. Biochem., 226 (1995) 148.

    Article  Google Scholar 

  10. Pinko, C., Margosiak, S.A., Vanderpool, D., Gutowski, J.C., Condon, B. and Kan, C.-C., J. Biol. Chem., 270 (1995) 23634.

    Article  PubMed  CAS  Google Scholar 

  11. Meldal, M., Svendsen, I., Breddam, K. and Auzanneau, F.-I., Proc. Natl. Acad. Sci. USA, 91 (1994) 3314.

    Article  PubMed  CAS  Google Scholar 

  12. Meldal, M. and Svendsen, I., J. Chem. Soc. Perkin Trans. I, (1995) 1591.

    Article  Google Scholar 

  13. Taliani, M., Bianchi, E., Narjes, F., Fossatelli, M., Urbani, A., Steinkühler, C., De Francesco, R. and Pessi, A., Anal. Biochem., 240 (1996) 60.

    Article  PubMed  CAS  Google Scholar 

  14. Handa, B.K. and Keech, E., Int. J. Pept. Protein Res., 40 (1992) 66.

    Article  PubMed  CAS  Google Scholar 

  15. Atherton, E. and Sheppard, R.C., Solid Phase Peptide Synthesis, IRL Press, Oxford, U.K., 1989, pp. 134–137.

    Google Scholar 

  16. Bianchi E., Steinkühler, C., Taliani, M., Urbani, A., De Francesco, R. and Pessi, A., Anal. Biochem., 237 (1996) 239.

    Article  PubMed  CAS  Google Scholar 

  17. 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.

    Google Scholar 

  18. Sole, N.A. and Barany, G., J. Org. Chem., 57 (1992) 5399.

    Article  CAS  Google Scholar 

  19. Steinkühler, C., Tomei, L. and De Francesco, R., J. Biol. Chem., 271 (1996) 6367.

    Article  PubMed  Google Scholar 

  20. Cunningham, B.R., Hannah, J. and Jones, A.B., Tetrahedron Lett., 35 (1994) 9517.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints 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. Lett Pept Sci 4, 101–106 (1997). https://doi.org/10.1007/BF02443521

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02443521

Keywords

Navigation