Arrata, I, Grison, CM, Coubrough, HM orcid.org/0000-0003-2526-9252 et al. (5 more authors) (2019) Control of conformation in α-helix mimicking aromatic oligoamide foldamers through interactions between adjacent side-chains. Organic and Biomolecular Chemistry, 17. pp. 3861-3867. ISSN 1477-0520
Abstract
The design, synthesis and structural characterization of non-natural oligomers that adopt well-defined conformations, so called foldamers, is a key objective in developing biomimetic 3D functional architectures. For the aromatic oligoamide foldamer family, use of interactions between side-chains to control conformation is underexplored. The current manuscript addresses this objective through the design, synthesis and conformational analyses of model dimers derived from 3-O-alkylated para-aminobenzoic acid monomers. The O-alkyl groups on these foldamers are capable of adopting syn- or anti-conformers through rotation around the Ar–CO/NH axes. In the syn-conformation this allows the foldamer to act as a topographical mimic of the α-helix whereby the O-alkyl groups mimic the spatial orientation of the i and i + 4 side-chains from the α-helix. Using molecular modelling and 2D NMR analyses, this work illustrates that covalent links and hydrogen-bonding interactions between side-chains can bias the conformation in favour of the α-helix mimicking syn-conformer, offering insight that may be more widely applied to control secondary structure in foldamers.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | This journal is © The Royal Society of Chemistry 2019. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. (https://creativecommons.org/licenses/by/3.0/) |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Biological Sciences (Leeds) > School of Molecular and Cellular Biology (Leeds) The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Organic Chemistry (Leeds) |
Funding Information: | Funder Grant number Leverhulme Trust RPG-2013-65 |
Depositing User: | Symplectic Publications |
Date Deposited: | 04 Mar 2019 10:21 |
Last Modified: | 25 Jun 2023 21:44 |
Status: | Published |
Publisher: | Royal Society of Chemistry |
Identification Number: | 10.1039/C9OB00123A |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:143147 |