A rapidly photo-activatable light-up fluorescent nucleoside and its application in DNA base variation sensing

Chem Commun (Camb). 2016 Jun 30;52(55):8545-8. doi: 10.1039/c6cc03098j.

Abstract

A new DNA building block (d(Tet)U) bearing a tetrazole and allyloxy group at N-phenyl ring linked through an aminopropynyl linker to the 5-position of 2'-deoxyuridine was synthesized. The modified DNA can be lit up via a photoinduced intramolecular tetrazole-alkene cycloaddition reaction, but quenched when the fully-matched double strand is formed. This conspicuous difference in fluorescence could open a door for DNA single nucleotide polymorphism (SNP) typing.

MeSH terms

  • Alkenes / chemistry
  • Cycloaddition Reaction
  • DNA / chemistry*
  • DNA / genetics*
  • Fluorescent Dyes / chemistry*
  • Light*
  • Nucleosides / chemistry*
  • Polymorphism, Single Nucleotide*
  • Tetrazoles / chemistry

Substances

  • Alkenes
  • Fluorescent Dyes
  • Nucleosides
  • Tetrazoles
  • 1H-tetrazole
  • DNA