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

被引：136
|
作者：
Liu, Tao [1 ]
Qiao, Jennifer X. [2 ]
Poss, Michael A. [2 ]
Yu, Jin-Quan [1 ]
机构：
[1] Scripps Res Inst TSRI, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
[2] Bristol Myers Squibb Co, Dept Discovery Chem, POB 5400, Princeton, NJ 08543 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 36期
关键词：
alkynylation; C-H activation; drug conjugation; palladium; peptides; ALPHA-AMINO-ACIDS; N-METHYLATION; PEPTIDES; BONDS; ARYLATION; PROTEINS; DIVERSIFICATION; RECEPTOR;
D O I：
10.1002/anie.201706367
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
引用
收藏
页码：10924 / 10927
页数：4
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