Stabilising Peptoid Helices Using Non‐Chiral Fluoroalkyl Monomers

Gimenez, D.; Aguilar, J.A.; Bromley, E.H.C.; Cobb, S.L.

doi:10.1002/anie.201804488

Stabilising Peptoid Helices Using Non‐Chiral Fluoroalkyl Monomers

Gimenez, D.; Aguilar, J.A.; Bromley, E.H.C.; Cobb, S.L.

Authors

D. Gimenez

Dr Juan Aguilar Malavia j.a.aguilar@durham.ac.uk
Solution NMR Service Senior Manager

Professor Elizabeth Bromley e.h.c.bromley@durham.ac.uk
Professor

Professor Steven Cobb s.l.cobb@durham.ac.uk
Professor

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.

Citation

Gimenez, D., Aguilar, J., Bromley, E., & Cobb, S. (2018). Stabilising Peptoid Helices Using Non‐Chiral Fluoroalkyl Monomers. Angewandte Chemie International Edition, 57(33), 10549-10553. https://doi.org/10.1002/anie.201804488

Journal Article Type	Article
Acceptance Date	May 23, 2018
Online Publication Date	Jun 27, 2018
Publication Date	Aug 13, 2018
Deposit Date	May 29, 2018
Publicly Available Date	Jun 29, 2018
Journal	Angewandte Chemie International Edition
Print ISSN	1433-7851
Electronic ISSN	1521-3773
Publisher	Wiley
Peer Reviewed	Peer Reviewed
Volume	57
Issue	33
Pages	10549-10553
DOI	https://doi.org/10.1002/anie.201804488

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Advance online version © 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.