Post-synthetic functionalization of tryptophan protected peptide sequences through indole (C-2) photocatalytic alkylation
Rafaely N. Lima, José A. C. Delgado, Darlon I. Bernardi, Roberto G. S. Berlinck, Nikolaos Kaplaneris, Lutz Ackermann, Márcio W. Paixão
Abstract
We report a selective, mild, and efficient C-H functionalization of tryptophan and tryptophan-containing peptides with activated α-bromo-carbonyl compounds under visible-light irradiation. The protocol efficiency is outlined by the wide substrate scope and excellent tolerance of sensitive functional groups present in the amino acid side chains. The method can be successfully extended to access pharmaco-peptide conjugate scaffolds.
Topics & Concepts
TryptophanSurface modificationIndole testAlkylationChemistryPhotocatalysisPeptideCombinatorial chemistryPhotochemistryOrganic chemistryCatalysisBiochemistryAmino acidPhysical chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsFluorine in Organic Chemistry