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

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Conformational switching of a foldamer in a multicomponent system by ph-filtered selection between competing noncovalent interactions. / Brioche, Julien; Pike, Sarah; Tshepelevitsh, Sofja; Leito, Ivo; Morris, Gareth; Webb, Simon; Clayden, Jonathan.

In: Journal of the American Chemical Society, Vol. 137, No. 20, 27.05.2015, p. 6680-6691.

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Brioche, Julien ; Pike, Sarah ; Tshepelevitsh, Sofja ; Leito, Ivo ; Morris, Gareth ; Webb, Simon ; Clayden, Jonathan. / Conformational switching of a foldamer in a multicomponent system by ph-filtered selection between competing noncovalent interactions. In: Journal of the American Chemical Society. 2015 ; Vol. 137, No. 20. pp. 6680-6691.

Bibtex

@article{7972b303f3e444d696b899ca773f7403,
title = "Conformational switching of a foldamer in a multicomponent system by ph-filtered selection between competing noncovalent interactions",
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.",
author = "Julien Brioche and Sarah Pike and Sofja Tshepelevitsh and Ivo Leito and Gareth Morris and Simon Webb and Jonathan Clayden",
year = "2015",
month = may,
day = "27",
doi = "10.1021/jacs.5b03284",
language = "English",
volume = "137",
pages = "6680--6691",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "20",

}

RIS

TY - JOUR

T1 - Conformational switching of a foldamer in a multicomponent system by ph-filtered selection between competing noncovalent interactions

AU - Brioche, Julien

AU - Pike, Sarah

AU - Tshepelevitsh, Sofja

AU - Leito, Ivo

AU - Morris, Gareth

AU - Webb, Simon

AU - Clayden, Jonathan

PY - 2015/5/27

Y1 - 2015/5/27

N2 - 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.

AB - 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.

U2 - 10.1021/jacs.5b03284

DO - 10.1021/jacs.5b03284

M3 - Article

VL - 137

SP - 6680

EP - 6691

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 20

ER -