Preparation of peptide p-nitroanilides using an aryl hydrazine resin.
[reaction: see text] 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.
Chemical Biology and Nuclear Sciences Division, Lawrence Livermore National Laboratory, Lawrence Livermore National Laboratory, 7000 East Avenue, Livermore, California 94550, USA.
Youngeun
Y
Kwon
Kelly
K
Welsh
Alexander R
AR
Mitchell
Julio A
JA
Camarero
D000813:Anilides / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D006834:Hydrazines / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis*
D000813:Anilides; D006834:Hydrazines; D010455:Peptides; C029424:hydrazine