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Angew Chem Int Ed Engl. 2018 Aug 13;57(33):10549-10553. doi: 10.1002/anie.201804488. Epub 2018 Jun 27.

Stabilising Peptoid Helices Using Non-Chiral Fluoroalkyl Monomers.

Author information

1
Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, UK.
2
Department of Physics, Durham University, South Road, Durham, DH1 3LE, UK.

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.

KEYWORDS:

NMR spectroscopy; fluorine; peptidomimetics; peptoids; secondary structure

PMID:
29846037
PMCID:
PMC6099454
DOI:
10.1002/anie.201804488
[Indexed for MEDLINE]
Free PMC Article

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