Warnock, Toyah MC;
Rajkumar, Sundaram;
Fitzpatrick, Matthew P;
Serpell, Christopher J;
Dingwall, Paul;
Knipe, Peter C;
(2021)
Chiral, sequence-definable foldamer-derived macrocycles.
Chemical Science
, 12
(47)
pp. 15632-15636.
10.1039/d1sc05021d.
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Abstract
Nature's oligomeric macromolecules have been a long-standing source of inspiration for chemists producing foldamers. Natural systems are frequently conformationally stabilised by macrocyclisation, yet this approach has been rarely adopted in the field of foldamer chemistry. Here we present a new class of chiral cyclic trimers and tetramers formed by macrocyclisation of open-chain foldamer precursors. Symmetrical products are obtained via a [2 + 2] self-assembly approach, while full sequence control is demonstrated through linear synthesis and cyclisation of an unsymmetrical trimer. Structural characterisation is achieved through a combined X-ray and DFT approach, which indicates the tetramers adopt a near-planar conformation, while the trimers adopt a shallow bowl-like shape. Finally, a proof-of-concept experiment is conducted to demonstrate the macrocycles' capacity for cation binding.
| Type: | Article |
|---|---|
| Title: | Chiral, sequence-definable foldamer-derived macrocycles |
| Location: | England |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1039/d1sc05021d |
| Publisher version: | https://doi.org/10.1039/d1sc05021d |
| Language: | English |
| Additional information: | © The Author(s), 2021. This is an Open Access article distributed under the terms of the Creative Commons Attribution Licence (CC BY 3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. https://creativecommons.org/licenses/by/3.0/ |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10204803 |
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