Efficient labelling of enzymatically synthesized vinyl-modified DNA by an inverse-electron-demand Diels-Alder reaction

Chem Commun (Camb). 2014 Sep 25;50(74):10827-9. doi: 10.1039/c4cc04332d.

Abstract

Many applications in biotechnology and molecular biology rely on modified nucleotides. Here, we present an approach for the postsynthetic labelling of enzymatically synthesized vinyl-modified DNA by Diels-Alder reaction with inverse electron demand using a tetrazine. Labelling proceeds very efficiently and supersedes several known approaches.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocatalysis
  • Cycloaddition Reaction
  • DNA / biosynthesis*
  • DNA / chemistry
  • DNA-Directed DNA Polymerase / metabolism
  • Deoxyadenosines / chemistry
  • Deoxyadenosines / metabolism
  • Deoxyuridine / analogs & derivatives
  • Deoxyuridine / chemistry
  • Deoxyuridine / metabolism
  • Electrons
  • Vinyl Compounds / chemistry*

Substances

  • Deoxyadenosines
  • Vinyl Compounds
  • 5-vinyl-2'-deoxyuridine
  • DNA
  • DNA-Directed DNA Polymerase
  • Deoxyuridine