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Fluorinated aromatic monomers as building blocks to control α-peptoid conformation and structure.

Gimenez, Diana and Zhou, Guangfeng and Hurley, Matthew F. D. and Aguilar, Juan A. and Voelz, Vincent A. and Cobb, Steven L. (2019) 'Fluorinated aromatic monomers as building blocks to control α-peptoid conformation and structure.', Journal of the American Chemical Society., 141 (8). pp. 3430-3434.

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.

Item Type:Article
Full text:(AM) Accepted Manuscript
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Status:Peer-reviewed
Publisher Web site:https://doi.org/10.1021/jacs.8b13498
Publisher 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
Date accepted:09 February 2019
Date deposited:17 May 2019
Date of first online publication:09 February 2019
Date first made open access:09 February 2020

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