Chemoselective and site-selective peptide and native protein modification enabled by aldehyde auto-oxidation

Chem Commun (Camb). 2017 Jan 16;53(5):959-962. doi: 10.1039/c6cc09555k. Epub 2017 Jan 3.

Abstract

We report a chemoselective and site-selective formylation of ε-amine in native proteins. The aldehyde auto-oxidation re-routing, regulated generation of formate, and reversible N-terminus protection drive the transformation. It labels a single ε-amine in a pool of its copies, other nucleophilic residues, and α-amine. The extension of the methodology leads to site-selective acylation.