Preparation of peptide p-nitroanilides using an aryl hydrazine resin
Preparation of peptide p-nitroanilides using an aryl hydrazine resin
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DOI：
10.1021/ol048417n
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发表时间：
2004-10-14
期刊：
影响因子：
5.2
通讯作者：
Camarero, JA
中科院分区：
文献类型：
--
作者：
Kwon, Y;Welsh, K;Camarero, JA
肽对硝基苯胺是研究蛋白酶活性的有用化合物;然而，对硝基苯胺的弱亲核性使其制备困难。我们描述了一种新的有效的方法为Fmoc为基础的合成肽对硝基苯胺使用芳基肼树脂。肽酰肼树脂的温和氧化产生与弱亲核试剂有效反应的高反应性酰基二氮烯。我们已经制备了几种肽对硝基苯胺，包括来自B的致死因子蛋白酶的底物。炭疽病
(GRAPHICS)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.