文献类型：期刊文献

英文题名：Alkali-metal hexamethyldisilazide initiated polymerization on alpha-amino acid N-substituted N-carboxyanhydrides for facile polypeptoid synthesis

作者：Wu, Yueming[1];Zhou, Min[2];Chen, Kang[2];Chen, Sheng[2];Xiao, Ximian[2];Ji, Zhemin[2];Zou, Jingcheng[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, Frontiers Sci Ctr Materiobiol & Dynam Chem, Sch Mat Sci & Engn, Res Ctr Biomed Mat,Minist Educ,Key Lab Ultrafine, Shanghai 200237, Peoples R China

年份：2021

卷号：32

期号：5

起止页码：1675

外文期刊名：CHINESE CHEMICAL LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000647702900014)】；

基金：This research was supported by the National Natural Science Foundation of China (Nos. 22075078, 21774031, 21861162010), the Natural Science Foundation of Shanghai (No. 118ZR1410300), the National Key Research and Development Program of China (No. 2016YFC1100401), the National Natural Science Foundation of China for Innovative Research Groups (No. 51621002), Program of Shanghai Academic/Technology Research Leader (No. 20XD142 1400), Research program of State Key Laboratory of Bioreactor Engineering, the Fundamental Research Funds for the Central Universities (No. 22221818014).

语种：英文

外文关键词：Polypeptoids; Peptide mimics; N-carboxyanhydrides (NNCA); Lithium hexamethyldisilazide; Sodium hexamethyldisilazide; Potassium hexamethyldisilazide; Ring-opening polymerization; Inactive NNCA

摘要：Polypeptoids have been explored as mimics of polypeptides, owing to polypeptoids' superior stability upon proteolysis. Polypeptoids can be synthesized from one-pot ring-opening polymerization of amino acid N-substituted N-carboxyanhydrides (NNCAs). However, the speed of polymerization of NNCAs can be very slow, especially for NNCAs bearing a bulky N-substitution group. This hindered the exploration on polypeptoids with more diverse structures and functions. Therefore, it is in great need to develop advanced strategies that can accelerate the polymerization on inactive NNCAs. Hereby, we report that lithium/sodium/potassium hexamethyldisilazide (Li/Na/KHMDS) initiates a substantially faster polymerization on NNCAs than do commonly used amine initiators, especially for NNCAs with bulky N substitution group. This fast NNCA polymerization will increase the structure diversity and application of polypeptoids as synthetic mimics of polypeptides. (c) 2021 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.