文献类型：期刊文献

英文题名：Facile synthesis of polypeptoids bearing bulky sidechains via urea accelerated ring-opening polymerization of α-amino acid N-substituted N-carboxyanhydrides

作者：Chen, Kang[1];Wu, Yueming[1];Wu, Xue[2];Zhou, Min[2];Zhou, Ruiyi[2];Wang, Jiangzhou[2];Xiao, Ximian[2];Yuan, Yuan[2];Liu, Runhui[1,2]

机构：[1]East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Shanghai Frontiers Sci Ctr Optogenet Techn Cell M, Frontiers Sci Ctr Mat & Dynam Chem, Res Ctr Biomed Mat,Minist Educ,Key Lab Ultrafine, Shanghai 200237, Peoples R China

年份：2022

卷号：13

期号：3

起止页码：420

外文期刊名：POLYMER CHEMISTRY

收录：;EI(收录号：20220611586515);WOS:【SCI-EXPANDED(收录号:WOS:000731078400001)】；

基金：This research was supported by the National Natural Science Foundation of China (No. 22075078, 21774031, 21861162010, 31800801), Program of Shanghai Academic/Technology Research Leader (20XD1421400), Research Program of State Key Laboratory of Bioreactor Engineering, and the Fundamental Research Funds for the Central Universities (JKD01211520). We also thank the staff members of the Mass Spectrometry System at the National Facility for Protein Science in Shanghai (NFPS), Zhangjiang Lab, China for providing technical support and assistance in data collection and analysis.

语种：英文

外文关键词：Amines - Amino acids - Catalysis - Hydrogen bonds - Metabolism - Ring opening polymerization - Substitution reactions

摘要：Polypeptoids, as synthetic mimics of polypeptides, exhibit a variety of biological functions and excellent proteolytic stability. Polypeptoids can be synthesized by the ring-opening polymerization of alpha-amino acid N-substituted N-carboxyanhydrides (NNCAs); however, they suffer from the generally slow reactivity and poor stability of NNCAs, especially those with bulky substitutes. This long-standing challenge greatly limits the synthesis of polypeptoids with diverse structures. Herein, we found that commercially available 1,3-bis[3,5-bis(trifluoromethyl)phenyl]urea can greatly accelerate the primary amine-initiated ring-opening polymerization of NNCAs by activating the NNCA carbonyl via hydrogen bonding interactions. Urea-catalyzed NNCA polymerization is compatible with diverse NNCAs in preparing polypeptoids with variable polymer lengths and narrow dispersity and is especially suitable for inactive NNCAs bearing bulky N-substitutes, such as cyclohexyl-NNCA. This urea-catalyzed NNCA polymerization strategy will substantially increase the structural diversity and functional study of polypeptoids, implying wider and diverse applications of these polypeptide mimics.