Design, synthesis and conformational analyses of bifacial benzamide based foldamers

Silvia Rodriguez-Marin, Natasha S. Murphy, Helena J. Shepherd, Andrew J. Wilson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


The design, synthesis and conformational analyses of novel backbones represents a key focus of research that underpins efforts to exploit foldamers (i) in a biological setting e.g. as inhibitors of protein-protein interactions (PPIs) and (ii) for the purposes of constructing functional architectures that adopt defined tertiary and quaternary folds. The current manuscript addresses a need to develop aromatic oligoamide backbones that are regioisomeric in terms of backbone connectivity and/or functionalized on more than one face. We describe the design, synthesis and comparative conformational analyses of foldamers derived from 2-, 3- and 2,5-O-alkylated derivatives of para-aminobenzoic acid, and, derived from 2-,3- and 2,5-O-alkylated derivatives of 1,4-diaminobenzene/terephthalic acid monomers. Analysis of the accessible conformational space for these oligomers indicates that despite different connectivity they can adopt conformations that position side chains in a manner that mimic the i, i + 3, i + 4 of an α-helix.

Original languageEnglish
Pages (from-to)104187-104192
Number of pages6
JournalRSC Advances
Issue number126
Publication statusPublished - 9 Dec 2015

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry 2015.

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering


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