Mutually antagonistic molecular clips: symmetry-breaking non-covalent bonds at the chiral-nonchiral interface.

ABSTRACT: 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 symmetry-breaking, in conjunc

SUBMITTER: Bae S 

PROVIDER: S-EPMC11775822 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature