Letters in Peptide Science

, Volume 7, Issue 6, pp 347–351 | Cite as

An efficient Fmoc strategy for the rapid synthesis of peptide para-nitroanilides

  • G. Abbenante
  • D. Leung
  • T. Bond
  • D. P. Fairlie


A new strategy has been developed for the rapid synthesis ofpeptide para-nitroanilides (pNA). The method involves derivatization of commercially available tritylchloride resin(TCP-resin) with 1,4-phenylenediamine, subsequent coupling withdesired amino acids by the standard Fmoc protocol, and oxidationof the intermediate para-aminoanilides (pAA) with Oxone®. This procedure allows easy assembly of the desired para-aminoanilides (pAA) on standard resin and efficient oxidation and purification of the corresponding para-nitroanilides (pNA). The method allows easy access to any desired peptide para-nitroanilides, which are useful substrates for the characterization and study of proteolytic enzymes.

chromogenic substrates oxidation Oxone® para-nitroanilides solid-phase synthesis 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    For some examples of the use of peptide para-nitroanilides see; Hou, W.C., Chen, H.J., Chen, T.E. and Lin, Y.H., Electrophoresis 20, (1999), 486; Gurtu, V., Kain, S.R. and Zhang, G., Analytical Biochemistry 251, (1997), 98; Laine, J., Beattie, M. and LeBel, D., Pancreas 8, (1993), 383; Claeson, G., Aurell, L., Friberger, P., Gustavsson, S. and Karlsson, G., Haemostasis, 7 (1978) 62 and references cited therein.Google Scholar
  2. 2.
    Irie, K., Mohan, P.M., Sasaguri, Y., Putnak, R. and Padmanabhan, R., Gene, 75 (1989) 197.Google Scholar
  3. 3.
    Alsina, J., Yokum T.S., Albericio, F. and Barany, G., J. Org. Chem., 64 (1999) 8761.Google Scholar
  4. 4.
    Hojo, K., Maeda. M., Iguchi, S., Smith, T., Okamoto, H. and Kawasaki, K., Chem. Pharm. Bull., 48 (2000) 1740.Google Scholar
  5. 5.
    Bernhardt, A., Drewello, M. and Schutkowski, M., J. Peptide Research, 50 (1997) 143.Google Scholar
  6. 6.
    Kaspari, A., Schierhorn, A. and SchutKowski, M., Int. J. Peptide Protein Res., 48 (1996) 486.Google Scholar
  7. 7.
    Burdick, P.J., Struble, M.E. and Burnier, J., Tetrahedron Letters, 34 (1993) 2589.Google Scholar
  8. 8.
    Mergler, M., Dick, F., Gosteli, J. and Nyfeler, R., Letters in Peptide Science, 7 (2000) 1.Google Scholar
  9. 10.
    Kennedy, R.J. and Stock, R.M., J. Org. Chem., 25 (1960) 1901.Google Scholar
  10. 11.
    Webb, K.S. and Seneviratne, V., Tetrahedron Letters, 36 (1995) 2377.Google Scholar

Copyright information

© Kluwer Academic Publishers 2000

Authors and Affiliations

  • G. Abbenante
    • 1
  • D. Leung
    • 2
  • T. Bond
    • 2
  • D. P. Fairlie
    • 2
  1. 1.Institute for Molecular BioscienceUniversity of Queensland, St. LuciaBrisbaneAustralia
  2. 2.Institute for Molecular BioscienceUniversity of Queensland, St. LuciaBrisbaneAustralia

Personalised recommendations