ArticleOrganic letters2020
Probing the Mechanism of Photoaffinity Labeling by Dialkyldiazirines through Bioorthogonal Capture of Diazoalkanes.
Article in Organic letters, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 30 citations in OpenAlex.
- Assessment of Protein Conformation via Diazirine-Promoted Oxidation of Methionine and Tryptophan Residues.Analytical chemistry · 2026Article
- Inherent MS-cleavability of diazirine photo-cross-links enables residue-level structural analysis.Nature communications · 2026Article
- Bifunctional Lipid-Protein Cross-linking Efficiency and Reaction Products.Journal of the American Chemical Society · 2026Article
- Development of Second-Generation Acyl Silane Photoaffinity Probes for Cellular Chemoproteomic Profiling.ACS chemical biology · 2025Article
- Dissecting diazirine photo-reaction mechanism for protein residue-specific cross-linking and distance mapping.Nature communications · 2024Article
- Photoproximity Labeling from Single Catalyst Sites Allows Calibration and Increased Resolution for Carbene Labeling of Protein Partners In Vitro and on Cells.ACS central science · 2024Article
- A fluorescent photoaffinity probe for formyl peptide receptor 1 labelling in living cells.RSC chemical biology · 2023Article
- Design and Evaluation of a Cyclobutane Diazirine Alkyne Tag for Photoaffinity Labeling in Cells.Journal of the American Chemical Society · 2022Article
- Developing Photoaffinity Probes for Dopamine Receptor DACS chemical neuroscience · 2022Article
- Inverse Drug Discovery identifies weak electrophiles affording protein conjugates.Current opinion in chemical biology · 2022Review
- Photo-Brook rearrangement of acyl silanes as a strategy for photoaffinity probe design.Chemical science · 2022Article
- Photochemical protein modification in complex biological environments: recent advances and considerations for future chemical methods development.Biological chemistry · 2022Article
- Flipping the Switch: Innovations in Inducible Probes for Protein Profiling.ACS chemical biology · 2021Review
- Photoaffinity labelling strategies for mapping the small molecule-protein interactome.Organic & biomolecular chemistry · 2021Review
- Evaluation of fully-functionalized diazirine tags for chemical proteomic applications.Chemical science · 2021Article
- Labeling Preferences of Diazirines with Protein Biomolecules.Journal of the American Chemical Society · 2021Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
Dialkyldiazirines have emerged as reagents of choice for biological photoaffinity labeling studies. The mechanism of crosslinking has dramatic consequences for biological applications where instantaneous labeling is desirable, as carbene insertions display different chemoselectivity and are much faster than competing mechanisms involving diazo or ylide intermediates. Here, deuterium labeling and diazo compound trapping experiments are employed to demonstrate that both carbene and diazo mechanisms operate in the reactions of a dialkyldiazirine motif that is commonly utilized for biological applications. For the fraction of intermolecular labeling that does involve a carbene mechanism, direct insertion is not necessarily involved, as products derived from a carbonyl ylide are also observed. We demonstrate that a strained cycloalkyne can intercept diazo compound intermediates and serve as a bioorthogonal probe for studying the contribution of the diazonium mechanism of photoaffinity labeling on a model protein under aqueous conditions.
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