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Stabilising peptoid helices using non-chiral fluoroalkyl monomers.

Gimenez, D. and Aguilar, J.A. and Bromley, E.H.C. and Cobb, S.L. (2018) 'Stabilising peptoid helices using non-chiral fluoroalkyl monomers.', Angewandte chemie international edition., 57 (33). pp. 10549-10553.

Abstract

Stability towards protease degradation combined with modular synthesis has made peptoids of considerable interest in the fields of chemical biology, medicine, and biomaterials. Given their tertiary amide backbone, peptoids lack the capacity to hydrogen‐bond, and as such, controlling secondary structure can be challenging. The incorporation of bulky, charged, or chiral aromatic monomers can be used to control conformation but such building blocks limit applications in many areas. Through NMR and X‐ray analysis we demonstrate that non‐chiral neutral fluoroalkyl monomers can be used to influence the Kcis/trans equilibria of peptoid amide bonds in model systems. The cis‐isomer preference displayed is highly unprecedented given that neither chirality nor charge is used to control the peptoid amide conformation. The application of our fluoroalkyl monomers in the design of a series of linear peptoid oligomers that exhibit stable helical structures is also reported.

Item Type:Article
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Status:Peer-reviewed
Publisher Web site:https://doi.org/10.1002/anie.201804488
Publisher statement:© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Date accepted:23 May 2018
Date deposited:29 June 2018
Date of first online publication:27 June 2018
Date first made open access:29 June 2018

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