Letters in Peptide Science

, Volume 7, Issue 6, pp 347–351

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

Article

DOI: 10.1007/BF02443598

Cite this article as:
Abbenante, G., Leung, D., Bond, T. et al. Lett Pept Sci (2000) 7: 347. doi:10.1007/BF02443598

Summary

A new strategy has been developed for the rapid synthesis of peptide para-nitroanilides (pNA). The method involves derivatization of commercially available tritylchloride resin (TCP-resin) with 1,4-phenylenediamine, subsequent coupling with desired amino acids by the standard Fmoc protocol, and oxidation of 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.

Key words

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

Abbreviations

pNA

para-nitroanilide,p-nitroanilide

pAA

para-aminoanilide,p-aminoanilide

DMF

N,N-dimethylformamide

rp-HPLC

reversed phase high performance liquid chromatography

DIPEA

N,N-diisopropylethylamine

Fmoc

9-fluorenylmethyloxycarbonyl

DCM

dichloromethane

HBTU

2-(H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium, hexafluorophosphate

Copyright information

© Kluwer Academic Publishers 2001

Authors and Affiliations

  • G. Abbenante
    • 1
  • D. Leung
    • 1
  • T. Bond
    • 1
  • D. P. Fairlie
    • 1
  1. 1.Institute for Molecular BioscienceUniversity of QueenslandBrisbaneAustralia

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