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Palladium(II)-Catalyzed Site-Selective C(sp3 )-H Alkynylation of Oligopeptides: A Linchpin Approach for Oligopeptide-Drug Conjugation.

ABSTRACT: The palladium(II)-catalyzed C(sp3 )-H alkynylation of oligopeptides was developed with tetrabutylammonium acetate as a key additive. Through molecular design, the acetylene motif served as a linchpin to introduce a broad range of carbonyl-containing pharmacophores onto oligopeptides, thus providing a chemical tool for the synthesis and modification of novel oligopeptide-pharmacophore conjugates by C-H functionalization. Dipeptide conjugates with coprostanol and estradiol were synthesized by this method for potential application in targeted drug delivery to tumor cells with overexpressed nuclear hormone receptors.

SUBMITTER: Liu T

PROVIDER: S-EPMC5572133 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Palladium(II)-Catalyzed Site-Selective C(sp3 )-H Alkynylation of Oligopeptides: A Linchpin Approach for Oligopeptide-Drug Conjugation.

Liu Tao T Qiao Jennifer X JX Poss Michael A MA Yu Jin-Quan JQ

Angewandte Chemie (International ed. in English) 20170807 36

The palladium(II)-catalyzed C(sp3 )-H alkynylation of oligopeptides was developed with tetrabutylammonium acetate as a key additive. Through molecular design, the acetylene motif served as a linchpin to introduce a broad range of carbonyl-containing pharmacophores onto oligopeptides, thus providing a chemical tool for the synthesis and modification of novel oligopeptide-pharmacophore conjugates by C-H functionalization. Dipeptide conjugates with coprostanol and estradiol were synthesi ...[more]

PMID: 28714148

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