Electrochemical chemoselective hydroxyl group transformation: anthranilic acyl modification of tyrosine bioconjugations

Abstract

Herein, we report an electrochemically promoted chemoselective hydroxyl group transformation for accessing tyrosine-containing biomolecules with valuable anthranilic acid derivatives. Notably, this method utilizes TBAF as an electrolyte and hydrogen-bonding additive, highlighting the unique possibilities associated with electrochemical activation methods, whereby the tyrosine residue can be well labelled with high chemo- and site-selectivity as well as excellent conversion under simple, mild and neutral conditions. Furthermore, proteins and cyclic peptide drugs could be well tagged by valuable anthranilic acid derivatives under buffer conditions without decomposition.