Post-synthetic functionalization of tryptophan protected peptide sequences through indole (C-2) photocatalytic alkylation?

Chemical Communications Pub Date: 2021-05-10 DOI: 10.1039/D1CC01822A

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.

Graphical abstract: Post-synthetic functionalization of tryptophan protected peptide sequences through indole (C-2) photocatalytic alkylation
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