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J Am Chem Soc. 2019 Feb 27;141(8):3430-3434. doi: 10.1021/jacs.8b13498. Epub 2019 Feb 15.

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

Author information

1
Department of Chemistry , Durham University , South Road , Durham DH1 3LE , U.K.
2
Department of Chemistry , Temple University , Philadelphia , Pennsylvania 19122 , United States.

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.

PMID:
30739443
DOI:
10.1021/jacs.8b13498

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