Enantiopure FeII4L4 cages bind steroids stereoselectively

作者：Gen Li, Tanya K. Ronson, Roy Lavendomme, Zehuan Huang, Carles Fuertes‐Espinosa, Dawei Zhang, Jonathan R. Nitschke · 发表于：Chem · 年份：2023 · DOI：10.1016/j.chempr.2023.03.011 · 被引用次数：52 · 研究领域：Supramolecular Chemistry and Complexes、Supramolecular Self-Assembly in Materials、Molecular Sensors and Ion Detection

Chiral recognition underpins many biological processes, including signaling and enzymatic transformations. Mimicry of the natural systems that include these processes can provide an understanding of their fundamental mechanisms and enable the design of synthetic systems capable of achieving similar functions. However, reported synthetic hosts can only recognize small, simple chiral guests. Here, we report the self-assembly of a triazatruxene trialdehyde subcomponent into enantiopure Fe II 4 L 4 cages. Their chirotopic properties and well-enclosed cavities enable these cages to recognize complex steroids through non-covalent interactions, as elucidated by X-ray crystallography. These recognition events occur enantioselectively and diastereoselectively, spanning moderate to exclusive differentiation. Notably, one cage enantiomer binds one equivalent of canrenone, whereas the other enantiomer binds two equivalents. Microcalorimetry experiments clarify the interplay of enthalpy and entropy during enantioselective binding.