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- Title
Cysteine-Selective Modification of Peptides and Proteins via Desulfurative C-C Bond Formation.
- Authors
Griffiths, Rhys C.; Smith, Frances R.; Diyuan Li; Wyatt, Jasmine; Rogers, David M.; Long, Jed E.; Cusin, Lola M. L.; Tighe, Patrick J.; Layfield, Robert; Hirst, Jonathan D.; Müller, Manuel M.; Mitchell, Nicholas J.
- Abstract
The site-selective modification of peptides and proteins facilitates the preparation of targeted therapeutic agents and tools to interrogate biochemical pathways. Among the numerous bioconjugation techniques developed to install groups of interest, those that generate C(sp³)-C(sp³) bonds are significantly underrepresented despite affording proteolytically stable, biogenic linkages. Herein, a visible-light-mediated reaction is described that enables the site-selective modification of peptides and proteins via desulfurative C(sp³)-C(sp³) bond formation. The reaction is rapid and high yielding in peptide systems, with comparable translation to proteins. Using this chemistry, a range of moieties is installed into model systems and an effective PTM-mimic is successfully integrated into a recombinantly expressed histone.
- Subjects
PEPTIDES; PROTEINS; MOIETIES (Chemistry); POST-translational modification
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 16, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202202503