Azidopropylvinylsulfonamide as a New Bifunctional Click Reagent for Bioorthogonal Conjugations: Application for DNA-Protein Cross-Linking

Chemistry. 2015 Nov 2;21(45):16091-102. doi: 10.1002/chem.201502209. Epub 2015 Sep 17.

Abstract

N-(3-Azidopropyl)vinylsulfonamide was developed as a new bifunctional bioconjugation reagent suitable for the cross-linking of biomolecules through copper(I)-catalyzed azide-alkyne cycloaddition and thiol Michael addition reactions under biorthogonal conditions. The reagent is easily clicked to an acetylene-containing DNA or protein and then reacts with cysteine-containing peptides or proteins to form covalent cross-links. Several examples of bioconjugations of ethynyl- or octadiynyl-modified DNA with peptides, p53 protein, or alkyne-modified human carbonic anhydrase with peptides are given.

Keywords: biotransformations; click chemistry; conjugation; nucleic acids; proteins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Azides / chemistry*
  • Biological Phenomena
  • Carbonic Anhydrases / chemistry*
  • Carbonic Anhydrases / metabolism
  • Catalysis
  • Click Chemistry
  • Copper / chemistry
  • Cycloaddition Reaction
  • DNA / chemistry*
  • DNA / metabolism
  • Humans
  • Indicators and Reagents / chemistry*
  • Peptides / chemistry*
  • Peptides / metabolism
  • Sulfhydryl Compounds / chemistry*
  • Sulfonamides / chemistry*
  • Vinyl Compounds / chemistry*

Substances

  • Alkynes
  • Azides
  • Indicators and Reagents
  • N-(3-azidopropyl)vinylsulfonamide
  • Peptides
  • Sulfhydryl Compounds
  • Sulfonamides
  • Vinyl Compounds
  • Copper
  • DNA
  • Carbonic Anhydrases