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.
Kwon
Youngeun
Y
Chemical Biology and Nuclear Sciences Division, Lawrence Livermore National Laboratory, Lawrence Livermore National Laboratory, 7000 East Avenue, Livermore, California 94550, USA.
Welsh
Kelly
K
Mitchell
Alexander R
AR
Camarero
Julio A
JA
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