Preparation of peptide p-nitroanilides using an aryl hydrazine resin

Youngeun Kwon, Kelly Welsh, Alexander R. Mitchell, Julio A. Camarero

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

(Chemical Equation Presented) Peptide p-nitroanilides are useful compounds for studying protease activity; however, the poor nucleophilicity of p-nitroaniline makes their preparation difficult. We describe a new efficient approach for the Fmoc-based synthesis of peptide p-nitroanilides using an aryl hydrazine resin. Mild oxidation of the peptide hydrazide resin yields a highly reactive acyl diazene that efficiently reacts with weak nucleophiles. We have prepared several peptide p-nitroanilides, including substrates for the Lethal Factor protease from B. anthracis.

Original languageEnglish
Pages (from-to)3801-3804
Number of pages4
JournalOrganic Letters
Volume6
Issue number21
DOIs
StatePublished - 14 Oct 2004

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