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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 ?-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.

SUBMITTER: San Segundo M

PROVIDER: S-EPMC6853082 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Pd-catalyzed site-selective C(sp<sup>2</sup>)-H radical acylation of phenylalanine containing peptides with aldehydes.

San Segundo Marcos M Correa Arkaitz A

Chemical science 20190807 38

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(sp<sup>2</sup>)-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 ...[more]

PMID: 31803461

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