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手性客体在笼外的选择性结合诱导 AL 四面体形阴离子笼的立体特异性。

Site-Selective Binding of Peripheral Chiral Guests Induces Stereospecificity in AL Tetrahedral Anion Cages.

机构信息

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an 710069, China.

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.

出版信息

J Am Chem Soc. 2020 Apr 1;142(13):6304-6311. doi: 10.1021/jacs.0c00882. Epub 2020 Mar 23.

DOI:10.1021/jacs.0c00882
PMID:32168449
Abstract

Herein we report an unprecedented chiral induction of anion-coordination-driven tetrahedra (AL-type) by peripheral guests, -, -α-methylcholine and -, -β-methylcholine, which are bound along the tetrahedral edges in a highly site-specific fashion. This "peripheral templation", which has proven indispensable for the formation of tetrahedral structure, is also an effective approach to encoding chiral information to the tetrahedron. Moreover, the site-selective binding of chiral choline derivatives to the anion cage with induced one-handedness may imply applications of such metal-free, labile systems in the study of biological processes such as selective recognition of structurally similar molecules.

摘要

在此,我们报告了一种前所未有的手性诱导方法,即通过外围客体(-,-α-甲基胆碱和-,-β-甲基胆碱)的阴离子配位驱动四面体(AL 型)。这些客体沿着四面体的边缘以高度特异性的方式结合,从而实现了四面体的手性诱导。这种“外围模板”对于四面体结构的形成是必不可少的,也是向四面体编码手性信息的有效方法。此外,手性胆碱衍生物与阴离子笼的选择性结合具有诱导的单一手性,这可能意味着这种无金属、不稳定的体系在手性分子的选择性识别等生物过程的研究中有应用前景。

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