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 language | English |
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Pages (from-to) | 3801-3804 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 6 |
Issue number | 21 |
DOIs | |
State | Published - 14 Oct 2004 |