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Redox-Regulated and Guest-Driven Transformations of Aromatic Oligoamide Foldamers in Advanced Structures

Lu Yu, Dongyao Li, Chunmiao Ma, Brice Kauffmann, Sibei Liao, Quan Gan

2024Journal of the American Chemical Society12 citationsDOI

Abstract

In this study, we demonstrate that an aromatic oligoamide sequence assembles into a trimeric helix-turn-helix architecture with a disulfide linkage, and upon cleavage of this linkage, it reconstructs into an antiparallel double helix. The antiparallel double helix is accessible to encapsulate a diacid guest within its cavity, forming a 2:1 host-guest complex. In contrast, hydrogen-bonding interactions between the trimeric-assembled structure and guests induce a conformational shift in the trimeric helix, resulting in a cross-shaped double-helix complex at a 2:2 host-guest ratio. Interconversions between the trimeric helix and the antiparallel double helix, along with their respective host-guest complexes, can be initiated through thiol/disulfide redox-mediated regulation.

Topics & Concepts

ChemistryRedoxCombinatorial chemistryNanotechnologyOrganic chemistryMaterials scienceChemical Synthesis and AnalysisClick Chemistry and ApplicationsChemical Synthesis and Reactions
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