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Small peptide diversification through photoredox-catalyzed oxidative C-terminal modification

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Abstract

A photoredox-catalyzed oxidative decarboxylative coupling of small peptides is reported, giving access to a variety of N,O-acetals. They were used as intermediates for the addition of phenols and indoles, leading to novel peptide scaffolds and bioconjugates. Amino acids with nucleophilic side chains, such as serine, threonine, tyrosine and tryptophan, could also be used as partners to access tri- and tetrapeptide derivatives with non-natural cross-linking.

Graphical abstract: Small peptide diversification through photoredox-catalyzed oxidative C-terminal modification

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Article information


Submitted
09 Nov 2020
Accepted
22 Dec 2020
First published
07 Jan 2021

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021, Advance Article
Article type
Edge Article

Small peptide diversification through photoredox-catalyzed oxidative C-terminal modification

E. Le Du, M. Garreau and J. Waser, Chem. Sci., 2021, Advance Article , DOI: 10.1039/D0SC06180H

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