A.M.Butlerov Chemical Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia.
School of Pharmacy and Biomolecular Sciences, University of Brighton, Huxley Building, Moulsecoomb, Brighton, East Sussex BN2 4GJ, UK.
Int J Mol Sci. 2020 Sep 29;21(19):7206. doi: 10.3390/ijms21197206.
Novel water-soluble multifunctional pillar[]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (-CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and H NMR spectroscopy. This work demonstrates the first case of using -CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of -CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. This study may advance the design novel stereoselective catalysts and transmembrane amino acid channels.
合成了含有酰胺-铵-氨基酸部分的新型水溶性多功能支柱[]芳烃。根据取代基的性质，这些化合物表现出与（1S）-（+）-10-樟脑磺酸（-CSA）和甲基橙染料结合的优异能力，从而与两种客体形成一一复合物。通过紫外（UV）、圆二色（CD）和 H NMR 光谱证实了主客体配合物的形成。这项工作首次证明了使用-CSA 作为基于支柱[]芳烃的架构的非共价自组装的手性模板。结果表明，具有甘氨酸或 L-丙氨酸片段的支柱[]芳烃分别形成平均流体力学直径（d）为 165 和 238nm 的聚集体。已经确定，向含 L-丙氨酸的衍生物中添加-CSA 会导致形成具有 713nm 的 d 的微米级聚集体。这项研究可能会推进设计新型立体选择性催化剂和跨膜氨基酸通道。
