Stabilising Peptoid Helices Using Non-Chiral Fluoroalkyl Monomers

Angewandte Chemie
Diana GimenezSteven L Cobb

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.

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Citations

Sep 2, 2020·Chemical Communications : Chem Comm·Kevin L Bicker, Steven L Cobb
May 12, 2020·Frontiers in Chemistry·Amelia A FullerAlberto Ortega
Dec 24, 2018·Biopolymers·Amelia A FullerPrashanth Asuri
Nov 8, 2019·Acta Biomaterialia·Hannah R ReeseStefano Menegatti
Feb 9, 2021·ChemPlusChem·José Laxio ArenasSandrine Ongeri
Jul 6, 2021·Chemical Science·Carolynn M DavernCaroline Proulx
Feb 12, 2019·Journal of the American Chemical Society·Diana GimenezSteven L Cobb
Mar 14, 2019·The Journal of Organic Chemistry·Isabelle WellhöferChristian A Olsen
Aug 19, 2020·The Journal of Organic Chemistry·Isabelle WellhöferChristian A Olsen
Nov 26, 2019·Journal of the American Chemical Society·Andrew W WijayaRonald N Zuckermann
Jul 25, 2019·The Journal of Organic Chemistry·Assunta D'AmatoFrancesco De Riccardis
Dec 25, 2019·The Journal of Organic Chemistry·Maha RzeiguiClaude Taillefumier
Sep 10, 2021·Chemical Communications : Chem Comm·Trideep RajaleJennifer S Martinez
Oct 7, 2021·Chemical Communications : Chem Comm·Claudine Nicole HerlanStefan Bräse
Oct 14, 2021·The Journal of Organic Chemistry·Viraj C KirindaC Scott Hartley

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Methods Mentioned

BETA
NMR
circular dichroism
X‐ray

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