Light-Controlled Traceless Protein Labeling via Decaging Thio‑o‑naphthoquinone Methide Chemistry

We report the molecular design of a novel multifunctional reagent and its application for light-controlled selective protein labeling. This molecule integrates functions of protein–ligand recognition, bioconjugation, ligand cleavage, and photoactivation by merging the photochemistries of 2-nitrophen...

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Bibliographic Details
Published in:Organic letters 2022-09, Vol.24 (37), p.6816-6821
Main Authors: Yu, Huaibin, Wang, Shuangshuang, Huang, Jianjian, Fu, Yu, Wagner, Manfred, Weil, Tanja, Zhong, Fangrui, Zhao, Weining, Wu, Yuzhou
Format: Article
Language:English
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Summary:We report the molecular design of a novel multifunctional reagent and its application for light-controlled selective protein labeling. This molecule integrates functions of protein–ligand recognition, bioconjugation, ligand cleavage, and photoactivation by merging the photochemistries of 2-nitrophenylpropyloxycarbonyl and 3-hydroxymethyl-2-naphthol with an affinity ligand and fluorescein. Highly electrophilic o-naphthoquinone methide was photochemically released and underwent proximity-driven selective labeling with the protein of interest (e.g., carbonic anhydrases), which retains its native function after labeling.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02742