Molecular Recognition by Zn(II)-Capped Dynamic Foldamers

Natasha Eccles, Flavio della Sala, Bryden A.F. Le Bailly, George F.S. Whitehead, Jonathan Clayden*, Simon J. Webb

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

26 Downloads (Pure)

Abstract

Two α-aminoisobutyric acid (Aib) foldamers bearing Zn(II)-chelating N-termini have been synthesized and compared with a reported Aib foldamer that has a bis(quinolinyl)/mono(pyridyl) cap (BQPA group). Replacement of the quinolinyl arms of the BQPA-capped foldamer with pyridyl gave a BPPA-capped foldamer, then further replacement of the linking pyridyl with a 1,2,3-triazole gave a BPTA-capped foldamer. Their ability to relay chiral information from carboxylate bound to Zn(II) at the N-terminus to a glycinamide-based NMR reporter of conformational preference at the C-terminus was measured. The importance of the quinolinyl arms became readily apparent, as the foldamers with pyridyl arms were unable to report on the presence of chiral carboxylate in acetonitrile. Low solubility, X-ray crystallography and 1H NMR spectroscopy suggested that interfoldamer interactions inhibited carboxylate binding. However changing solvent to methanol revealed that the end-to-end relay of chiral information could be observed for the Zn(II) complex of the BPTA-capped foldamer at low temperature.

Original languageEnglish
Pages (from-to)338-345
Number of pages8
JournalChemistryOpen
Volume9
Issue number3
DOIs
Publication statusPublished - 1 Mar 2020

Keywords

  • molecular recognition
  • peptides
  • receptors
  • self-assembly
  • supramolecular chemistry

Fingerprint Dive into the research topics of 'Molecular Recognition by Zn(II)-Capped Dynamic Foldamers'. Together they form a unique fingerprint.

Cite this