JACS Publication: Editors Spotlight

The group of Jonathan Clayden, in collaboration with Simon Webb and Gareth Morris, recently reported in J. Am. Chem. Soc. a synthetic system that is able to ‘count protons’ ["Conformational Switching of a Foldamer in a Multicomponent System by pH-Filtered Selection between Competing Noncovalent Interactions" Julien Brioche, Sarah J. Pike, Sofja Tshepelevitsh, Ivo Leito, Gareth A. Morris, Simon J. Webb, and Jonathan Clayden J. Am. Chem. Soc., 2015, 137, 6680-6691]

The system consists of a mixture containing an achiral peptidomimetic molecule (a ‘foldamer’) carrying a basic binding site, plus a set of acidic chiral ligands with a range of pKa values.  As acids or bases are added to the system, the basic binding site is forced to pair with different components of the mixture, and as it does so, NMR-detectable conformational changes are induced in the peptide-like foldamer to which is it linked.  Conformational responsiveness to their environment is a key property of proteins involved in biological signal transduction, and this work provides a simple model of how this could be achieved in a synthetic system.  It represents an early step in exploiting the properties of conformationally dynamic foldamers in systems chemistry. The work was also highlighted as an ‘Editors Spotlight’ at J. Am. Chem. Soc. 2015, 137, 6111.

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