Journal article
The Bioorthogonal Isonitrile-Chlorooxime Ligation.
- Schäfer RJB Laboratory of Organic Chemistry , ETH Zurich, D-CHAB , Vladimir-Prelog-Weg 3 , Zurich 8093 , Switzerland.
- Monaco MR Laboratory of Organic Chemistry , ETH Zurich, D-CHAB , Vladimir-Prelog-Weg 3 , Zurich 8093 , Switzerland.
- Li M Laboratory of Organic Chemistry , ETH Zurich, D-CHAB , Vladimir-Prelog-Weg 3 , Zurich 8093 , Switzerland.
- Tirla A Laboratory of Organic Chemistry , ETH Zurich, D-CHAB , Vladimir-Prelog-Weg 3 , Zurich 8093 , Switzerland.
- Rivera-Fuentes P Laboratory of Organic Chemistry , ETH Zurich, D-CHAB , Vladimir-Prelog-Weg 3 , Zurich 8093 , Switzerland.
- Wennemers H Laboratory of Organic Chemistry , ETH Zurich, D-CHAB , Vladimir-Prelog-Weg 3 , Zurich 8093 , Switzerland.
- 2019-11-12
Published in:
- Journal of the American Chemical Society. - 2019
English
Bioorthogonal reactions are valuable tools for the selective labeling and imaging of natural products and proteins. Here, we present the reaction between isonitriles and chlorooximes as a ligation that proceeds quickly (k ≈ 1 M-1 s-1) and with high chemoselectivity in an aqueous environment. Imaging of metabolically labeled cell surface glycans underlined the tolerance of the ligation to common functional groups in cellular systems. Live-cell dual-labeling experiments revealed that the isonitrile-chlorooxime ligation is orthogonal to the strain-promoted azide-alkyne cycloaddition.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1021/jacs.9b07632
- PMID 31710811
- Persistent URL
- https://folia.unifr.ch/global/documents/275226
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