Laboratoire de Chimie, École Normale Supérieure de Lyon , CNRS, UCBL, 46, Allée d'Italie, F-69364 Lyon, France.
Org Lett. 2014 May 2;16(9):2374-7. doi: 10.1021/ol500706z. Epub 2014 Apr 15.
The first water-soluble hemicryptophane cage compound, 4, was synthesized in seven steps from commercially available products, and its complexation properties were studied. NMR and ITC experiments indicate that 4 is an efficient receptor for choline in water (ΔG° = -5.2 kcal mol(-1)). High substrate selectivity was achieved since no complexation was observed for its closely related substrates: glycine betaine and betaine aldehyde. Density functional theory calculations were performed to analyze the interactions that are involved in the formation of the inclusion complex.
首例水溶性半笼状笼形化合物 4 由市售产品经 7 步反应合成，并对其络合性能进行了研究。核磁和 ITC 实验表明 4 是水中胆碱的有效受体（ΔG°=-5.2 kcal mol(-1)）。由于其相关底物甘氨酸甜菜碱和甜菜醛没有络合，实现了高底物选择性。进行了密度泛函理论计算以分析参与形成包络复合物的相互作用。
