Malke Marlen, Barqawi Haitham, Binder Wolfgang H
Chair of Macromolecular Chemistry, Institute of Chemistry, Division of Technical and Macromolecular Chemistry, Faculty of Natural Sciences II (Chemistry, Physics and Mathematics), Martin-Luther-University Halle-Wittenberg, von-Danckelmann-Platz 4, Halle D-06120, Germany.
ACS Macro Lett. 2014 Apr 15;3(4):393-397. doi: 10.1021/mz500108n. Epub 2014 Apr 7.
A new biomimetic polymer containing a beta-turn mimetic element () was synthesized, using a combination of living carbocationic polymerization (LCCP), amidation, and "click" chemistry. Two different α-ω-functionalized polyisobutylenes (PIBs and ) bearing either an alkyne group (PIB ) or a primary amine group (PIB ) were directly synthesized via LCCP. The linking of the two PIB strands with the closely positioned carboxyl/azido moieties of a β-turn dipeptide (BTD) was achieved via a sequence of amidation reaction and the Cu-mediated azide/alkyne "click" reaction. By means of size exclusion chromatography (SEC), matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS), NMR spectroscopy, and LC/MALDI-TOF MS, a detailed structural proof of the β-turn mimetic PIB conjugate () was possible.
通过活性阳离子聚合（LCCP）、酰胺化反应和“点击”化学相结合的方法，合成了一种含有β-转角模拟元件（）的新型仿生聚合物。通过LCCP直接合成了两种不同的α-ω-官能化聚异丁烯（PIB 和），分别带有炔基（PIB ）或伯胺基（PIB ）。通过酰胺化反应序列和铜介导的叠氮化物/炔烃“点击”反应，实现了两条PIB链与β-转角二肽（BTD）紧密定位的羧基/叠氮基部分的连接。借助尺寸排阻色谱（SEC）、基质辅助激光解吸/电离飞行时间质谱（MALDI-TOF MS）、核磁共振光谱（NMR）和液相色谱/基质辅助激光解吸/电离飞行时间质谱（LC/MALDI-TOF MS），可以对β-转角模拟PIB共轭物（）进行详细的结构验证。
