Angewandte Chemie - International Edition p. 8353 - 8357 (2016)
Update date:2022-08-03
Topics:
Sekirnik (née Measures), Angelina R.
Hewings, David S.
Theodoulou, Natalie H.
Jursins, Lukass
Lewendon, Katie R.
Jennings, Laura E.
Rooney, Timothy P. C.
Heightman, Tom D.
Conway, Stuart J.
A range of isoxazole-containing amino acids was synthesized that displaced acetyl-lysine-containing peptides from the BAZ2A, BRD4(1), and BRD9 bromodomains. Three of these amino acids were incorporated into a histone H4-mimicking peptide and their affinity for BRD4(1) was assessed. Affinities of the isoxazole-containing peptides are comparable to those of a hyperacetylated histone H4-mimicking cognate peptide, and demonstrated a dependence on the position at which the unnatural residue was incorporated. An isoxazole-based alkylating agent was developed to selectively alkylate cysteine residues in situ. Selective monoalkylation of a histone H4-mimicking peptide, containing a lysine to cysteine residue substitution (K12C), resulted in acetyl-lysine mimic incorporation, with high affinity for the BRD4 bromodomain. The same technology was used to alkylate a K18C mutant of histone H3.
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