Exploring the Histone Acylome through Incorporation of γ-Thialysine on Histone Tails

Bioconjug Chem. 2020 Mar 18;31(3):844-851. doi: 10.1021/acs.bioconjchem.0c00012. Epub 2020 Feb 27.

Abstract

Histone lysine acetyltransferases (KATs) catalyze the transfer of the acetyl group from acetyl Coenzyme A to lysine residues in histones and nonhistone proteins. Here, we report biomolecular studies on epigenetic acetylation and related acylation reactions of lysine and γ-thialysine, a cysteine-derived lysine mimic, which can be site-specifically introduced to histone peptides and histone proteins. Enzyme assays demonstrate that human KATs catalyze an efficient acetylation and propionylation of histone peptides that possess lysine and γ-thialysine. Enzyme kinetics analyses reveal that lysine- and γ-thialysine-containing histone peptides exhibit indistinguishable Km values, whereas small differences in kcat values were observed. This work highlights that γ-thialysine may act as a representative and easily accessible lysine mimic for chemical and biochemical examinations of post-translationally modified histones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Biocatalysis*
  • Cysteine / analogs & derivatives*
  • Cysteine / metabolism
  • Histone Acetyltransferases / chemistry
  • Histone Acetyltransferases / metabolism
  • Histones / chemistry*
  • Histones / metabolism*
  • Humans
  • Kinetics
  • Models, Molecular
  • Protein Conformation

Substances

  • Histones
  • S-2-aminoethyl cysteine
  • Histone Acetyltransferases
  • Cysteine