Facile functionalization of peptide nucleic acids (PNAs) for antisense and single nucleotide polymorphism detection

Org Biomol Chem. 2017 Aug 16;15(32):6710-6714. doi: 10.1039/c7ob01592e.

Abstract

In this report, we show how a convenient on-resin copper-click functionalization of azido-functionalized peptide nucleic acids (PNAs) allows various PNA-based detection strategies. Firstly, a thiazole orange (TO) clicked PNA probe facilitates a binary readout when combined with F/Q labeled DNA, giving increased sensitivity for antisense detection. Secondly, our TO-PNA conjugate also allows single nucleotide polymorphism detection. Since antisense detection is also possible in the absence of the TO label, our sensing platform based on azido-d-ornithine containing PNA even allows for additional and more advanced functionalization and sensing strategies.

MeSH terms

  • Azides / chemistry
  • Benzothiazoles / chemistry
  • Copper / chemistry
  • DNA, Antisense / analysis*
  • DNA, Antisense / chemistry
  • Molecular Probes / chemistry*
  • Peptide Nucleic Acids / chemical synthesis
  • Peptide Nucleic Acids / chemistry*
  • Polymorphism, Single Nucleotide*
  • Quinolines / chemistry

Substances

  • Azides
  • Benzothiazoles
  • DNA, Antisense
  • Molecular Probes
  • Peptide Nucleic Acids
  • Quinolines
  • thiazole orange
  • Copper