Ding Xing-Xing, Li Bing-Tong, Dong Lin
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Org Lett. 2025 Jan 24;27(3):863-868. doi: 10.1021/acs.orglett.4c04535. Epub 2025 Jan 14.
Dehydrophenylalanine has a characteristic unsaturated double bond that makes it indispensable in the context of peptides and proteins. In this study, we report the Pd-catalyzed C(sp)-H arylation of dehydroalanine-containing peptides with arylthianthrenium salts under mild and base free conditions, which provides efficient access to dehydrophenylalanine-containing peptides. This approach enables the efficient coupling of different drug scaffolds and bioactive molecules to the peptides. Remarkably, the method could be used for the concise synthesis of tentoxin and its analogue.
脱氢苯丙氨酸具有独特的不饱和双键，这使其在肽和蛋白质领域不可或缺。在本研究中，我们报道了在温和且无碱条件下，钯催化含脱氢丙氨酸的肽与芳基噻蒽鎓盐的C(sp)-H芳基化反应，该反应为合成含脱氢苯丙氨酸的肽提供了有效途径。这种方法能够实现不同药物支架和生物活性分子与肽的高效偶联。值得注意的是，该方法可用于简洁合成细交链孢菌酮酸及其类似物。
