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Fluorinated Aromatic Monomers as Building Blocks To Control α-Peptoid Conformation and Structure

Gimenez, Diana; Zhou, Guangfeng; Hurley, Matthew F.D.; Aguilar, Juan A.; Voelz, Vincent A.; Cobb, Steven L.

Fluorinated Aromatic Monomers as Building Blocks To Control α-Peptoid Conformation and Structure Thumbnail


Authors

Diana Gimenez

Guangfeng Zhou

Matthew F.D. Hurley

Juan A. Aguilar

Vincent A. Voelz



Abstract

Peptoids are peptidomimetics of interest in the fields of drug development and biomaterials. However, obtaining stable secondary structures is challenging, and designing these requires effective control of the peptoid tertiary amide cis/trans equilibrium. Herein, we report new fluorine-containing aromatic monomers that can control peptoid conformation. Specifically, we demonstrate that a fluoro-pyridine group can be used to circumvent the need for monomer chirality to control the cis/trans equilibrium. We also show that incorporation of a trifluoro-methyl group (NCF3Rpe) rather than a methyl group (NRpe) at the α-carbon of a monomer gives rise to a 5-fold increase in cis-isomer preference.

Citation

Gimenez, D., Zhou, G., Hurley, M. F., Aguilar, J. A., Voelz, V. A., & Cobb, S. L. (2019). Fluorinated Aromatic Monomers as Building Blocks To Control α-Peptoid Conformation and Structure. Journal of the American Chemical Society, 141(8), 3430-3434. https://doi.org/10.1021/jacs.8b13498

Journal Article Type Article
Acceptance Date Feb 9, 2019
Online Publication Date Feb 9, 2019
Publication Date Feb 27, 2019
Deposit Date May 17, 2019
Publicly Available Date Feb 9, 2020
Journal Journal of the American Chemical Society
Print ISSN 0002-7863
Electronic ISSN 1520-5126
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 141
Issue 8
Pages 3430-3434
DOI https://doi.org/10.1021/jacs.8b13498

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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.8b13498





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