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Ugi Reaction of Natural Amino Acids: A General Route toward Facile Synthesis of Polypeptoids for Bioapplications

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journal contribution
posted on 30.08.2016, 16:50 authored by Xiaojie Zhang, Shixue Wang, Jing Liu, Zhigang Xie, Shifang Luan, Chunsheng Xiao, Youhua Tao, Xianhong Wang
Polypeptoids represent a significant class of synthetic analogues of natural polypeptides with potential biomimetic applications in materials, catalysis, and pharmaceuticals, but their simple and general synthesis still remains a key challenge. Herein, we demonstrate that Ugi reaction of natural amino acids leads to structurally diverse polypeptoids, including γ- and δ-, as well as poly­(ε-peptoid)­s, under mild conditions (open to air, room temperature, and catalyst free). Moreover, this strategy also offers manifold opportunities to introduce functional groups such as fluorescent and clickable alkenes groups into polypeptoids. Such poly­(ε-peptoid)­s not only exhibit good biocompatibility and antibacterial activity, but perform very effectively as a drug-delivery system. The bacterial inhibition rate of poly­(ε-peptoid) was up to 88.8% at concentration of 20 μg mL–1 in comparison to 61.8% of the poly­(ε-lysine) control. Overall, this study offers us a general methodology toward facile preparation of polypeptoids for bioapplications.