Conformational switching of a foldamer in a multicomponent system by ph-filtered selection between competing noncovalent interactions

Research output: Contribution to journalArticlepeer-review

Authors

  • Julien Brioche
  • Sofja Tshepelevitsh
  • Ivo Leito
  • Gareth Morris
  • Simon Webb
  • Jonathan Clayden

Colleges, School and Institutes

Abstract

Biomolecular systems are able to respond to their chemical environment through reversible, selective, noncovalent intermolecular interactions. Typically, these interactions induce conformational changes that initiate a signaling cascade, allowing the regulation of biochemical pathways. In this work, we describe an artificial molecular system that mimics this ability to translate selective noncovalent interactions into reversible conformational changes. An achiral but helical foldamer carrying a basic binding site interacts selectively with the most acidic member of a suite of chiral ligands. As a consequence of this noncovalent interaction, a global absolute screw sense preference, detectable by 13C NMR, is induced in the foldamer. Addition of base, or acid, to the mixture of ligands competitively modulates their interaction with the binding site, and reversibly switches the foldamer chain between its left and right-handed conformations. As a result, the foldamer–ligand mixture behaves as a biomimetic chemical system with emergent properties, functioning as a “proton-counting” molecular device capable of providing a tunable, pH-dependent conformational response to its environment.

Details

Original languageEnglish
Pages (from-to)6680-6691
Number of pages12
JournalJournal of the American Chemical Society
Volume137
Issue number20
Early online date14 May 2015
Publication statusPublished - 27 May 2015