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Palladium(II)‐Catalyzed Site‐Selective C(sp 3 )−H Alkynylation of Oligopeptides: A Linchpin Approach for Oligopeptide–Drug Conjugation
Author(s) -
Liu Tao,
Qiao Jennifer X.,
Poss Michael A.,
Yu JinQuan
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201706367
Subject(s) - pharmacophore , oligopeptide , chemistry , dipeptide , conjugate , stereochemistry , combinatorial chemistry , palladium , peptide , catalysis , organic chemistry , biochemistry , mathematics , mathematical analysis
The palladium(II)‐catalyzed C(sp 3 )−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.