A Scalable and High-Yield Strategy for the Synthesis of Sequence-Defined Macromolecules
A Scalable and High-Yield Strategy for the Synthesis of Sequence-Defined Macromolecules
复制标题
DOI：
10.1002/anie.201509398
复制
发表时间：
2016-01-18
影响因子：
16.6
通讯作者：
Meier, Michael A. R.
中科院分区：
文献类型：
--
作者：
Solleder, Susanne C.;Zengel, Deniz;Meier, Michael A. R.
描述了序列定义的十聚体的有效合成、其表征及其通过自复分解的直接二聚化。为此，设计了一种单保护的AB单体，并通过迭代Passerini三组分反应（P-3CR）和随后的脱保护来合成具有10个不同且可选择的侧链的十聚体。高效的程序提供了优异的产率，并允许这样的完美定义的大分子的多克规模的合成。在合成结束时引入烯烃，允许所得十聚体的自复分解反应，以提供分子量为7046.40gmol（-1）的序列限定的20聚体。通过NMR和IR光谱、GPC和GPC与ESI-MS联用以及质谱（FAB和轨道阱ESI-MS）对所获得的低聚物进行仔细表征。
The efficient synthesis of a sequence-defined decamer, its characterization, and its straightforward dimerization through self-metathesis are described. For this purpose, a monoprotected AB monomer was designed and used to synthesize a decamer bearing ten different and selectable side chains by iterative Passerini three-component reaction (P-3CR) and subsequent deprotection. The highly efficient procedure provided excellent yields and allows for the multigram-scale synthesis of such perfectly defined macromolecules. An olefin was introduced at the end of the synthesis, allowing the self-metathesis reaction of the resulting decamer to provide a sequence-defined 20-mer with a molecular weight of 7046.40gmol(-1). The obtained oligomers were carefully characterized by NMR and IR spectroscopy, GPC and GPC coupled to ESI-MS, and mass spectrometry (FAB and orbitrap ESI-MS).