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Issue 17, 2017
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Signal transduction in oligoamide foldamers by selective non-covalent binding of chiral phosphates at a urea binding site

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Abstract

The transduction of biological signals depends on the spatial communication of conformational change. We report a synthetic mimic of this signal transduction process in which non-covalent binding induces a change in the position of equilibrium between two rapidly interconverting screw-sense conformers of a synthetic helical polyamide. Selectivity was achieved by incorporating at the N-terminus of the polyamide a urea-based anion recognition site capable of binding chiral phosphate anions. As a result of solvent-dependent binding, an induced conformational change propagates from the binding site through the amide chain, leading to a screw-sense preference detectable in the form of a chemical shift separation between two NMR active 13C labels. The remote induction of screw sense preference indicates successful communication of a signal originating solely from non-covalent binding.

Graphical abstract: Signal transduction in oligoamide foldamers by selective non-covalent binding of chiral phosphates at a urea binding site

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Article information


Submitted
17 Mar 2017
Accepted
30 Mar 2017
First published
31 Mar 2017

Org. Biomol. Chem., 2017,15, 3585-3589
Article type
Communication

Signal transduction in oligoamide foldamers by selective non-covalent binding of chiral phosphates at a urea binding site

K. Gratzer, V. Diemer and J. Clayden, Org. Biomol. Chem., 2017, 15, 3585
DOI: 10.1039/C7OB00660H

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