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Issue 38, 2019
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Pd-catalyzed site-selective C(sp2)–H radical acylation of phenylalanine containing peptides with aldehydes

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Abstract

The site-selective functionalization of C–H bonds within a peptide framework remains a challenging task of prime synthetic importance. Herein, the first Pd-catalyzed δ-C(sp2)–H acylation of Phe containing peptides with aldehydes is described. This oxidative coupling is distinguished by its site-specificity, tolerance of sensitive functional groups, scalability, and enantiospecificity and exhibits entire chemoselectivity for Phe motifs over other amino acid units. The compatibility of this dehydrogenative acylation platform with a number of oligopeptides of high structural complexity illustrates its ample opportunities for the late-stage peptide modification and bioconjugation.

Graphical abstract: Pd-catalyzed site-selective C(sp2)–H radical acylation of phenylalanine containing peptides with aldehydes

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Supplementary files

Article information


Submitted
10 Jul 2019
Accepted
06 Aug 2019
First published
07 Aug 2019

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

Chem. Sci., 2019,10, 8872-8879
Article type
Edge Article

Pd-catalyzed site-selective C(sp2)–H radical acylation of phenylalanine containing peptides with aldehydes

M. San Segundo and A. Correa, Chem. Sci., 2019, 10, 8872
DOI: 10.1039/C9SC03425K

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