Enhanced Aqueous Suzuki鈥揗iyaura Coupling Allows Site-Specific Polypeptide 18F-Labeling

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• 作者：Zhanghua Gao ; V茅ronique Gouverneur ; Benjamin G. Davis
• 刊名：Journal of the American Chemical Society
• 出版年：2013
• 出版时间：September 18, 2013
• 年：2013
• 卷：135
• 期：37
• 页码：13612-13615
• 全文大小：301K
• 年卷期：v.135,no.37(September 18, 2013)
• ISSN：1520-5126

文摘

The excesses of reagents used in protein chemistry are often incompatible with the reduced or even inverse stoichiometries used for efficient radiolabeling. Analysis and screening of aqueous Pd(0) ligand systems has revealed the importance of a guanidine core and the discovery of 1,1-dimethylguanidine as an enhanced ligand for aqueous Suzuki鈥揗iyaura cross-coupling. This novel Pd catalyst system has now allowed the labeling of small molecules, peptides, and proteins with the fluorine-18 prosthetic [¹⁸F]4-fluorophenylboronic acid. These findings now enable site-specific protein ¹⁸F-labeling under biologically compatible conditions using a metal-triggered reaction.