Oxidation-induced generation of a mild electrophile for proximity-enhanced protein-protein crosslinking

Chem Commun (Camb). 2018 Apr 19;54(33):4172-4175. doi: 10.1039/c8cc01639a.

Abstract

We report a strategy to introduce a reactive electrophile into proteins through the conversion of a chemically inert group into a bioreactive group in response to an inducer molecule. This strategy was demonstrated by oxidation-induced and proximity-enhanced protein-protein crosslinking in the presence of a large excess of free nucleophile.

MeSH terms

  • Catalysis
  • Cross-Linking Reagents / chemical synthesis
  • Cross-Linking Reagents / chemistry*
  • Dansyl Compounds / chemistry
  • Escherichia coli
  • Ethylenediamines / chemistry
  • Fluorescent Dyes / chemistry
  • Glutathione Transferase / chemistry
  • Glutathione Transferase / genetics
  • Green Fluorescent Proteins / chemistry
  • Green Fluorescent Proteins / genetics
  • Hydrogen Peroxide / chemistry
  • Lysine / analogs & derivatives*
  • Lysine / chemical synthesis
  • Lysine / chemistry*
  • Lysine / genetics*
  • Methanosarcina barkeri
  • Molecular Probes / chemistry*
  • Molecular Probes / genetics
  • Mutation
  • Myoglobin / chemistry
  • Myoglobin / genetics
  • Oxidation-Reduction
  • Proteins / chemistry*
  • Proteins / genetics
  • Sulfoxides / chemistry
  • Tungsten Compounds / chemistry
  • Vinyl Compounds / chemical synthesis
  • Vinyl Compounds / chemistry*

Substances

  • Cross-Linking Reagents
  • Dansyl Compounds
  • Ethylenediamines
  • Fluorescent Dyes
  • Molecular Probes
  • Myoglobin
  • Proteins
  • Sulfoxides
  • Tungsten Compounds
  • Vinyl Compounds
  • Green Fluorescent Proteins
  • dansylethylenediamine
  • Hydrogen Peroxide
  • Glutathione Transferase
  • Lysine