Photoredox-Catalyzed Labeling of Hydroxyindoles with Chemoselectivity (PhotoCLIC) for Site-Specific Protein Bioconjugation

被引：9
|
作者：
Roy, Soumya Jyoti Singha [1 ]
Loynd, Conor [1 ]
Jewel, Delilah [1 ]
Canarelli, Sarah E. [1 ]
Ficaretta, Elise D. [1 ]
Pham, Quan A. [1 ]
Weerapana, Eranthie [1 ]
Chatterjee, Abhishek [1 ]
机构：
[1] Boston Coll, Dept Chem, 2609 Beacon St, Chestnut Hill, MA 02467 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 27期
关键词：
Bioconjugation; Chemoselectivity; Photoredox Catalysis; Protein Labeling; AMINO-ACID MUTAGENESIS; CLICK CHEMISTRY; GENETIC-CODE; 5-HYDROXYTRYPTOPHAN; FUNCTIONALIZATION; RESIDUES; PLATFORM; OXYGEN; CELLS;
D O I：
10.1002/anie.202300961
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
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页数：7
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