Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic Oxidative Cross-Coupling Reactions
Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic Oxidative Cross-Coupling Reactions
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DOI：
10.1002/anie.201913305
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发表时间：
2020-01-30
影响因子：
16.6
通讯作者：
Pappo, Doron
中科院分区：
文献类型：
--
作者：
Ben-Lulu, Mor;Gaster, Eden;Pappo, Doron
联芳基桥联环肽是一类结构多样、具有显著生物活性的天然产物。特别值得注意的是抗生素芳香霉素及其合成类似物G0775，它对革兰氏阴性菌具有很强的活性。在这里，我们提出了一种基于活化基团辅助催化氧化偶联的简单、灵活和可靠的策略，用于从天然氨基酸中组装联芳基桥联环肽。利用该合成方法制备了一系列天然和非天然联芳基桥联环肽，包括芳霉素/G0775和RP 66453环核。
Biaryl-bridged cyclic peptides comprise an intriguing class of structurally diverse natural products with significant biological activity. Especially noteworthy are the antibiotics arylomycin and its synthetic analogue G0775, which exhibits potent activity against Gram-negative bacteria. Herein, we present a simple, flexible, and reliable strategy based on activating-group-assisted catalytic oxidative coupling for assembling biaryl-bridged cyclic peptides from natural amino acids. The synthetic approach was utilized for preparing a number of natural and unnatural biaryl-bridged cyclic peptides, including arylomycin/G0775 and RP 66453 cyclic cores.