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.

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
• Public URL: https://durham-repository.worktribe.com/output/1296126