Post-synthetic functionalization of tryptophan protected peptide sequences through indole (C-2) photocatalytic
Rafaely N Lima1, José A C Delgado1, Darlon I Bernardi2
1Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos-UFSCar, Rodovia Washington Luís, km 235, SP-310, São Carlos, São Paulo 13565905, Brazil. mwpaixao@ufscar.br.
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.
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