Electrochemical Selenylation of Tyrosine Oligopeptides: A Novel Route to Benzo[b]furan-Functionalized Peptides

Abstract Benzo[b]furans are significant scaffolds in drug molecules and are prevalent structural components in natural products. Chemically encoded non-natural peptidomimetics have a substantial impact on pharmaceuticals by offering enhanced stability, improved cell permeability, and resistance to enzymatic degradation. Consequently, a strategy for the sustainable assembly of benzo[b]furan peptides through the electrochemical late-stage modification of tyrosine-derived peptides is proposed. This approach facilitates the multifunctional integration of various natural amino acids with tyrosine, as well as their subsequent functionalization. Notably, the resulting peptides exhibit favorable properties regarding biocompatibility and cellular uptake.