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

Author:

Singha Roy Soumya Jyoti1,Loynd Conor1,Jewel Delilah1,Canarelli Sarah E.1,Ficaretta Elise D.1,Pham Quan A.1,Weerapana Eranthie1,Chatterjee Abhishek1ORCID

Affiliation:

1. Department of Chemistry Boston College 2609 Beacon Street Chestnut Hill MA 02467 USA

Abstract

AbstractWe 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.

Funder

National Institute of General Medical Sciences

National Science Foundation

Publisher

Wiley

Subject

General Chemistry,Catalysis

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