Polymer Chemistry Research Group, Centre of Macromolecular Chemistry (CMaC), Department of Organic and Macromolecular Chemistry, Faculty of Science, Ghent University, Krijgslaan 281 S4-bis, Ghent, B-9000, Belgium.
Polymer Chemistry Laboratory, School of Engineering and Materials Science, Queen Mary, University of London, E1 4NS, London, UK.
Macromol Rapid Commun. 2017 Dec;38(24). doi: 10.1002/marc.201700500. Epub 2017 Oct 25.
A strategy for the synthesis of sequence-defined oligomers using a selective side-group insertion approach making use of thiophenol-catalyzed amidation reactions is herein reported. In this context, a new thiolactone-based, multistep, iterative protocol is designed, utilizing thioacrylates in combination with solid-phase synthesis for step-by-step growth, resulting in sequence-defined oligomers. Sequence definition and structure variation are introduced by substituting the thioacrylate side groups with a wide variety of amines. The step-by-step growth of the oligomers is followed by liquid chromatography-mass spectrometry and high-resolution mass spectroscopy to determine both conversion and purity.
本文报道了一种利用选择性侧基插入方法，通过使用噻吩酚催化的酰胺化反应来合成序列定义的低聚物的策略。在这种情况下，设计了一种新的基于硫内酯的多步迭代方案，使用硫代丙烯酸酯与固相合成相结合进行逐步生长，得到序列定义的低聚物。通过用各种胺取代硫代丙烯酸酯侧基来引入序列定义和结构变化。通过液相色谱-质谱和高分辨率质谱来跟踪低聚物的逐步生长，以确定转化率和纯度。
