Vinylsulfonamide and acrylamide modification of DNA for cross-linking with proteins

Angew Chem Int Ed Engl. 2013 Sep 27;52(40):10515-8. doi: 10.1002/anie.201303577. Epub 2013 Aug 12.

Abstract

Bioorthogonal covalent cross-linking of DNA-binding proteins (p53) to DNA was achieved through novel DNA probes bearing a reactive vinylsulfonamide (VS) group. The VS-modified dCTP served as building block for polymerase synthesis of modified DNA, which was readily conjugated with cysteine-containing peptides and proteins by Michael addition.

Keywords: DNA; DNA polymerase; Michael additions; bioorthogonal chemistry; proteins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylamide / chemical synthesis
  • Acrylamide / chemistry*
  • Cross-Linking Reagents / chemistry
  • DNA / chemical synthesis
  • DNA / chemistry*
  • DNA-Directed DNA Polymerase / chemistry
  • Ethylenes / chemistry
  • Models, Molecular
  • Proteins / chemistry*
  • Proteins / metabolism
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry*
  • Sulfonic Acids / chemistry
  • Vinyl Compounds / chemical synthesis
  • Vinyl Compounds / chemistry*

Substances

  • Cross-Linking Reagents
  • Ethylenes
  • Proteins
  • Sulfonamides
  • Sulfonic Acids
  • Vinyl Compounds
  • Acrylamide
  • DNA
  • DNA-Directed DNA Polymerase
  • ethylenesulfonic acid