Issue 38, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
10 jul 2019
Accepted
06 ago 2019
First published
07 ago 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 8872-8879

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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