光氧化还原催化的羟基吲哚的化学选择性标记（PhotoCLIC）用于定点蛋白质生物偶联。
Photoredox-Catalyzed Labeling of Hydroxyindoles with Chemoselectivity (PhotoCLIC) for Site-Specific Protein Bioconjugation.
机构信息
Department of Chemistry, Boston College, 2609 Beacon Street, Chestnut Hill, MA, 02467, USA.
出版信息
Angew Chem Int Ed Engl. 2023 Jul 3;62(27):e202300961. doi: 10.1002/anie.202300961. Epub 2023 May 23.
Abstract
We have developed a novel visible-light-catalyzed bioconjugation reaction, PhotoCLIC, that enables chemoselective attachment of diverse aromatic amine reagents onto a site-specifically installed 5-hydroxytryptophan residue (5HTP) on full-length proteins of varied complexity. The reaction uses catalytic amounts of methylene blue and blue/red light-emitting diodes (455/650 nm) for rapid site-specific protein bioconjugation. Characterization of the PhotoCLIC product reveals a unique structure formed likely through a singlet oxygen-dependent modification of 5HTP. PhotoCLIC has a wide substrate scope and its compatibility with strain-promoted azide-alkyne click reaction, enables site-specific dual-labeling of a target protein.
摘要
我们开发了一种新型的可见光催化生物偶联反应，即 PhotoCLIC，它可以使各种芳香胺试剂选择性地连接到全长蛋白质中特定位置安装的 5-羟色氨酸残基（5HTP）上。该反应使用亚甲基蓝和蓝/红色发光二极管（455/650nm）的催化量进行快速的特异性蛋白质生物偶联。PhotoCLIC 产物的表征揭示了一种可能通过 5HTP 依赖单线态氧的修饰形成的独特结构。PhotoCLIC 具有广泛的底物范围，并且与应变促进的叠氮-炔点击反应兼容，能够实现目标蛋白质的特异性双重标记。
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