Discovering Targets of Non-enzymatic Acylation by Thioester Reactivity Profiling

Cell Chem Biol. 2017 Feb 16;24(2):231-242. doi: 10.1016/j.chembiol.2017.01.002. Epub 2017 Feb 2.

Abstract

Non-enzymatic protein modification driven by thioester reactivity is thought to play a major role in the establishment of cellular lysine acylation. However, the specific protein targets of this process are largely unknown. Here we report an experimental strategy to investigate non-enzymatic acylation in cells. Specifically, we develop a chemoproteomic method that separates thioester reactivity from enzymatic utilization, allowing selective enrichment of non-enzymatic acylation targets. Applying this method to cancer cell lines identifies numerous candidate targets of non-enzymatic acylation, including several enzymes in lower glycolysis. Functional studies highlight malonyl-CoA as a reactive thioester metabolite that can modify and inhibit glycolytic enzyme activity. Finally, we show that synthetic thioesters can be used as novel reagents to probe non-enzymatic acylation in living cells. Our studies provide new insights into the targets and drivers of non-enzymatic acylation, and demonstrate the utility of reactivity-based methods to experimentally investigate this phenomenon in biology and disease.

Keywords: Warburg effect; acetylation; acylation; epigenetics; glycolysis; malonylation; metabolism; non-enzymatic; reactivity-based protein profiling; thioester.

MeSH terms

  • Acyl Coenzyme A / chemistry
  • Acyl Coenzyme A / metabolism
  • Acylation
  • Esters / chemistry
  • Esters / metabolism*
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Proteomics
  • Sulfhydryl Compounds / chemistry
  • Sulfhydryl Compounds / metabolism*
  • Tumor Cells, Cultured

Substances

  • Acyl Coenzyme A
  • Esters
  • Sulfhydryl Compounds