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Stabilising Peptoid Helices Using Non‐Chiral Fluoroalkyl Monomers
Author(s) -
Gimenez Diana,
Aguilar Juan A.,
Bromley Elizabeth H. C.,
Cobb Steven L.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201804488
Subject(s) - peptoid , monomer , peptidomimetic , chemistry , amide , hydrogen bond , chirality (physics) , combinatorial chemistry , peptide bond , circular dichroism , stereochemistry , organic chemistry , peptide , molecule , polymer , enzyme , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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 K cis/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.