Bae Sungryul, Jeong Younjae, Lee Dongwhan
Department of Chemistry, Seoul National University 1 Gwanak-ro, Gwanak-gu Seoul 08826 Korea
Chem Sci. 2025 Jan 7;16(8):3459-3469. doi: 10.1039/d4sc07655a. eCollection 2025 Feb 19.
The homochirality of life remains an unresolved scientific question. Prevailing models postulate that homochirality arose through mutual antagonism. In this mechanism, molecules of opposite handedness deactivate each other, amplifying even a small enantiomeric excess into a larger proportion. In this paper, we present chiral molecular clips that replicate this process. Through π-π stacking and complementary hydrogen bonds, shape-persistent clips of opposite chirality bind to each other more strongly than those of the same chirality, resulting in chiral amplification. This process was studied quantitatively, revealing a remarkably high degree (180-fold) of stereoselection, unmatched by any non-covalent assemblies reported to date. We demonstrate how this , in conjunction with the of the host, impacts the binding of nonchiral molecules. Our findings illustrate how chirality transfer and amplification occur non-covalently from hosts to guests, offering insights into the evolutionary origins of homochirality in life's molecular building blocks.
生命的同手性仍然是一个尚未解决的科学问题。主流模型假定同手性是通过相互拮抗作用产生的。在这种机制中，相反手性的分子会相互失活，将即使很小的对映体过量放大到更大的比例。在本文中，我们展示了能够复制这一过程的手性分子夹。通过π-π堆积和互补氢键，相反手性的形状持久夹相互之间的结合比相同手性的夹更强，从而导致手性放大。对这一过程进行了定量研究，揭示了极高程度（180倍）的立体选择性，这是迄今为止报道的任何非共价组装体都无法比拟的。我们展示了这一点与主体的[此处原文缺失相关内容]相结合如何影响非手性分子的结合。我们的研究结果说明了手性如何从主体非共价地转移和放大到客体，为生命分子构建块中同手性的进化起源提供了见解。
