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.

引用

页数：7

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