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Molecular Recognition by Zn(II)-Capped Dynamic Foldamers.

Natasha Eccles1,2, Flavio Della Sala1,2, Bryden A F Le Bailly1,3

  • 1Department of Chemistry University of Manchester Oxford Road Manchester M13 9PL UK.

Chemistryopen
|March 21, 2020
PubMed
Summary

Chiral information transfer in α-aminoisobutyric acid (Aib) foldamers was investigated. Pyridyl-containing foldamers showed limited chiral reporting, but a triazole-capped Aib foldamer relayed information in methanol, highlighting the role of N-terminal capping groups.

Keywords:
molecular recognitionpeptidesreceptorsself-assemblysupramolecular chemistry

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Biophysical Chemistry

Background:

  • α-Aminoisobutyric acid (Aib) foldamers are synthetic peptides with defined structures.
  • Zn(II) chelation can be used to control foldamer conformation and function.
  • Chiral information relay is crucial for developing molecular sensors and catalysts.

Purpose of the Study:

  • To synthesize and compare Aib foldamers with different N-terminal capping groups.
  • To investigate the ability of these foldamers to relay chiral information.
  • To understand the influence of capping group structure on foldamer properties and function.

Main Methods:

  • Synthesis of Aib foldamers with N-terminal Zn(II)-chelating groups.
  • Spectroscopic characterization including 1H NMR and X-ray crystallography.
  • Evaluation of chiral information relay in different solvent systems.

Main Results:

  • Foldamers with pyridyl arms showed limited ability to report chiral information due to poor solubility and interfoldamer interactions.
  • The bis(pyridyl)/pyridyl/triazole-amide (BPTA)-capped foldamer demonstrated end-to-end chiral information relay in methanol at low temperatures.
  • X-ray crystallography and NMR suggested that interfoldamer interactions impacted carboxylate binding.

Conclusions:

  • The N-terminal capping group significantly influences the chiral reporting ability of Aib foldamers.
  • Pyridyl arms are less effective than quinolinyl arms for reporting chiral information in acetonitrile.
  • Solvent choice and low temperatures can enable chiral information relay in specific Aib foldamer systems.