Facile synthetic method for peptoids bearing multiple azoles on side chains
Facile synthetic method for peptoids bearing multiple azoles on side chains
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DOI：
10.1002/pep2.24287
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发表时间：
2022-06-14
期刊：
影响因子：
2.4
通讯作者：
Seo，Jiwon
中科院分区：
文献类型：
--
作者：
Lee，Yen Jea;Park，Soyeon;Seo，Jiwon
天然金属酶通过利用多个咪唑部分来稳定金属中心。受自然界设计原理的启发，在配体中引入多个唑类化合物已成为构建过渡金属配合物的有效方法。在本文中，我们描述了类肽的合成后修饰，以在侧链上掺入多个唑。唑类（咪唑、吡唑、1，2，3-三唑和四唑）与含氯烷基的类肽之间的简单取代反应提供了获得各种含唑类肽的途径。从单个含氯烷基的类肽合成了10个含唑类肽，并评价了每种唑类对取代反应的效率。我们已经确定了几种含唑类肽能够与Cu（II）和Fe（III）结合。我们的合成方法可以有助于扩大类肽的化学多样性和开发新的类肽用于金属识别和催化。
Natural metalloenzymes stabilize metal centers by utilizing multiple imidazole moieties. Inspired by nature's design principles, the introduction of multiple azoles into ligands has been an effective method for constructing transition metal complexes. Herein, we describe a post‐synthetic modification of peptoids to incorporate multiple azoles on side chains. A simple substitution reaction between an azole (imidazole, pyrazole, 1,2,3‐triazole, and tetrazole) and a chloroalkyl‐containing peptoid provided access to a variety of azole‐containing peptoids. Ten azole‐containing peptoids were synthesized from a single chloroalkyl‐containing peptoid, and the efficiency of each azole for the substitution reaction was evaluated. We have identified that several of the azole‐containing peptoids are capable of binding with Cu(II) and Fe(III). Our synthetic approach can contribute to the expansion of peptoids' chemical diversity and the development of novel peptoids for metal recognition and catalysis.