文献类型：期刊文献

英文题名：Facile Synthesis of Thioether-Functionalized N-Substituted Glycine N-Thiocarboxyanhydride toward Well-Defined Thiopolypeptoids

作者：Ding, Yingdong[1];Feng, Chen[2];Jin, Sheng[1];Li, Yuxin[1];Tao, Xinfeng[1];Lin, Shaoliang[1]

机构：[1]East China Univ Sci & Technol, Sch Mat Sci & Engn, Shanghai Key Lab Adv Polymer Mat, Key Lab Ultrafine Mat,Minist Educ, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China

年份：2025

卷号：26

期号：9

起止页码：5694

外文期刊名：BIOMACROMOLECULES

收录：;EI(收录号：20253719145938);WOS:【SCI-EXPANDED(收录号:WOS:001548532400001)】；

基金：This work was supported by the National Natural Science Foundation of China (52325308 and 21901073) and the Natural Science Foundation of Shanghai (24ZR1416500).

语种：英文

外文关键词：Amino acids - Biomimetics - Substitution reactions

摘要：To synthesize functional polypeptoids, the most straightforward strategy involves designing tailored amino acids to generate corresponding N-substituted glycine N-carboxyanhydrides (NNCAs) or N-substituted glycine N-thiocarboxyanhydrides (NNTAs). An alternative route is offered by postpolymerization modification. However, the potential method of modifying NNCA and NNTA monomers to produce functional polypeptoids has received scant attention. Herein, we employed N-allylglycine N-thiocarboxyanhydride (NAG-NTA) as a versatile platform for the convenient synthesis of thioether-functionalized NNTAs via thiol-ene photoaddition. Controlled polymerizations of these thioether-functionalized NNTAs were achieved in CH2Cl2 at room temperature, catalyzed by benzoic acid and initiated by a primary amine, yielding well-defined thiopolypeptoids with relatively low dispersities (& Dstrok; < 1.29) and predictable molecular weights. The thermal properties and oxidation responsiveness of the thiopolypeptoids were investigated. Poly(ethylene glycol)-b-thiopolypeptoid self-assembled into micelles in water, whose size and morphologies could be tuned by treatment with H2O2, showing promise in the fields of bionics and biomedicine due to their excellent biocompatibility.