Site-Selective Installation of N^ϵ -Modified Sidechains into Peptide and Protein Scaffolds via Visible-Light-Mediated Desulfurative C-C Bond Formation.

ABSTRACT: Post-translational modifications (PTMs) enhance the repertoire of protein function and mediate or influence the activity of many cellular processes. The preparation of site-specifically and homogeneously modified proteins, to apply as tools to understand the biological role of PTMs, is a challenging task. Herein, we describe a visible-light-mediated desulfurative C(sp³ )-C(sp³ ) bond forming reaction that enables the site-selective installation of N^ϵ -modified sidechains into peptides and proteins of interest. Rapid, operationally simple, and tolerant to ambient atmosphere, we demonstrate the installation of a range of lysine (Lys) PTMs into model peptide systems and showcase the potential of this technology by site-selectively installing an N^ϵ Ac sidechain into recombinantly expressed ubiquitin (Ub).

SUBMITTER: Griffiths RC 

PROVIDER: S-EPMC9299887 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature