Kwon Youngeun, Welsh Kelly, Mitchell Alexander R, Camarero Julio A
Chemical Biology and Nuclear Sciences Division, Lawrence Livermore National Laboratory, Lawrence Livermore National Laboratory, 7000 East Avenue, Livermore, California 94550, USA.
Org Lett. 2004 Oct 14;6(21):3801-4. doi: 10.1021/ol048417n.
[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.
[反应：见正文] 肽对硝基苯胺是用于研究蛋白酶活性的有用化合物；然而，对硝基苯胺的亲核性较差，使得它们的制备困难。我们描述了一种使用芳基肼树脂基于Fmoc合成肽对硝基苯胺的新有效方法。肽酰肼树脂的温和氧化产生一种高反应性的酰基重氮烯，它能与弱亲核试剂有效反应。我们已经制备了几种肽对硝基苯胺，包括炭疽杆菌致死因子蛋白酶的底物。
