Synthetic Fluorogenic Peptides Reveal Dynamic Substrate Specificity of Depalmitoylases

Cell Chem Biol. 2019 Jan 17;26(1):35-47.e7. doi: 10.1016/j.chembiol.2018.10.005. Epub 2018 Nov 1.

Abstract

Palmitoylation is a post-translational modification involving the thioesterification of cysteine residues with a 16-carbon-saturated fatty acid. Little is known about rates of depalmitoylation or the parameters that dictate these rates. Here we report a modular strategy to synthesize quenched fluorogenic substrates for the specific detection of depalmitoylase activity and for mapping the substrate specificity of individual depalmitoylases. We demonstrate that human depalmitoylases APT1 and APT2, and TgPPT1 from the parasite Toxoplasma gondii, have distinct specificities that depend on amino acid residues distal to the palmitoyl cysteine. This information informs the design of optimal and non-optimal substrates as well as isoform-selective substrates to detect the activity of a specific depalmitoylase in complex proteomes. In addition to providing tools for studying depalmitoylases, our findings identify a previously unrecognized mechanism for regulating steady-state levels of distinct palmitoylation sites by sequence-dependent control of depalmitoylation rates.

Keywords: chemical probes; combinatorial libraries; depalmitoylases; dynamic palmitoylation; fluorogenic peptides; substrate specificity; thioesterases.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Female
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / metabolism*
  • Humans
  • Membrane Proteins / metabolism*
  • Mice
  • Mice, Inbred C57BL
  • Molecular Structure
  • Peptides / chemistry
  • Peptides / metabolism*
  • Substrate Specificity
  • Thiolester Hydrolases / metabolism*
  • Toxoplasma / metabolism

Substances

  • Fluorescent Dyes
  • Membrane Proteins
  • Peptides
  • LYPLA1 protein, human
  • LYPLA2 protein, human
  • Thiolester Hydrolases
  • PPT1 protein, human