Control of conformation in α-helix mimicking aromatic oligoamide foldamers through interactions between adjacent side-chains

Irene Arrata, Claire M. Grison, Heather M. Coubrough, Panchami Prabhakaran, Marc A. Little, Darren C. Tomlinson, Michael E. Webb, Andrew J. Wilson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The design, synthesis and structural characterization of non-natural oligomers that adopt well-defined conformations, so called foldamers, is a key objective in developing biomimetic 3D functional architectures. For the aromatic oligoamide foldamer family, use of interactions between side-chains to control conformation is underexplored. The current manuscript addresses this objective through the design, synthesis and conformational analyses of model dimers derived from 3-O-alkylated para-aminobenzoic acid monomers. The O-alkyl groups on these foldamers are capable of adopting syn- or anti-conformers through rotation around the Ar–CO/NH axes. In the syn-conformation this allows the foldamer to act as a topographical mimic of the α-helix whereby the O-alkyl groups mimic the spatial orientation of the i and i + 4 side-chains from the α-helix. Using molecular modelling and 2D NMR analyses, this work illustrates that covalent links and hydrogen-bonding interactions between side-chains can bias the conformation in favour of the α-helix mimicking syn-conformer, offering insight that may be more widely applied to control secondary structure in foldamers.
Original languageEnglish
Pages (from-to)3861-3867
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number15
DOIs
Publication statusPublished - 2 Apr 2019

Keywords

  • Amides
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Models Molecular
  • Molecular Conformation
  • Amino acids
  • Aromatic compounds
  • Biomimetic processes
  • Hydrogen Bonds
  • Nuclear magnetic resonance spectroscopy
  • Amide
  • Aminobenzoic acid
  • aromatic oligoamide
  • conformational analysis
  • functional architecture
  • hydrogen bonding interactions
  • secondary structures
  • spatial orientations
  • structural characterization
  • chemistry
  • molecular model

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Control of conformation in α-helix mimicking aromatic oligoamide foldamers through interactions between adjacent side-chains'. Together they form a unique fingerprint.

Cite this