ArticleJournal of the American Chemical Society2021
Labeling Preferences of Diazirines with Protein Biomolecules.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 89 papers.
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Who cites it
89 citing papers in PubMed, 194 citations in OpenAlex.
- Chemical reactions for the ligand-directed modification of native proteins.Chemical Society reviews · 2026Review
- Progress and challenges in traceless ligand-directed labelling chemistry.Communications chemistry · 2026Review
- Photosensitizer proximity labeling captures the lipid and protein interactomes.Nature chemical biology · 2026Article
- Small-molecule binding-site discovery using silyl ether-enabled chemoproteomics.Nature chemistry · 2026Article
- Identifying lipid-protein interactomes with functional lipid probes.Nature protocols · 2026Review
- Excited-State Intramolecular Proton Transfer Enables Self-Reporting Fluorescent Photoaffinity Labeling in Live Cells.Journal of the American Chemical Society · 2026Article
- Synthesis and Application of a Suite of 2,5-Aryl Tetrazole Photoaffinity-Based Probes for Profiling Microbial Carbohydrate and Mucin Metabolism in Gut Microbiota.ACS chemical biology · 2026Article
- Covalent Chemical Tagging of Transmembrane Transport Proteins Illuminates the Internalization Pathways of Xenosiderophores.Journal of the American Chemical Society · 2026Article
- Assessment of Protein Conformation via Diazirine-Promoted Oxidation of Methionine and Tryptophan Residues.Analytical chemistry · 2026Article
- Bifunctional Lipid-Protein Cross-linking Efficiency and Reaction Products.Journal of the American Chemical Society · 2026Article
- Lysine Targeting Group-Transfer Chimeras for Proximity Induction.Angewandte Chemie (International ed. in English) · 2026Article
- Photoclick chemistry led to the identification of HELLS as a helicase for DNA G-quadruplexes.Nucleic acids research · 2026Article
- Diazirines Beyond Photoaffinity Labeling: A Comprehensive Overview of Applications in Biological Sciences, Materials Chemistry, and NMR-Spectroscopy.Angewandte Chemie (International ed. in English) · 2026Review
- An Integrated Method for Profiling Lipid-Protein Interactions Using Multifunctional Lipid Probes.bioRxiv : the preprint server for biology · 2026Article
- Mass Spectrometry Proteomics: A Key to Faster Drug Discovery.Journal of medicinal chemistry · 2026Review
- Photoactivatable, Biomimetic Ligand photoMultiTASQ Traps DNA/RNA G‑Quadruplexes and Their Protein Binding Partners.ACS bio & med chem Au · 2025Article
- Energy-transfer photoproximity labelling in live cells using an organic cofactor.Nature chemistry · 2025Article
- All-optical visualization of specific molecules in the ultrastructural context of brain tissue.Nature biotechnology · 2025Article
- Development of Second-Generation Acyl Silane Photoaffinity Probes for Cellular Chemoproteomic Profiling.ACS chemical biology · 2025Article
- Harnessing platinum(IV) prodrugs as versatile photoinitiators and photocrosslinkers for multifunctional hydrogels and protein labeling.Nature communications · 2025Article
29 more citing papers are in PubMed but not listed here.
Corrections and comments
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Authors and funding
7 authors at 3 institutions in 1 country.
Funding
Abstract
Diazirines are widely used in photoaffinity labeling (PAL) to trap noncovalent interactions with biomolecules. However, design and interpretation of PAL experiments is challenging without a molecular understanding of the reactivity of diazirines with protein biomolecules. Herein, we report a systematic evaluation of the labeling preferences of alkyl and aryl diazirines with individual amino acids, single proteins, and in the whole cell proteome. We find that alkyl diazirines exhibit preferential labeling of acidic amino acids in a pH-dependent manner that is characteristic of a reactive alkyl diazo intermediate, while the aryl-fluorodiazirine labeling pattern reflects reaction primarily through a carbene intermediate. From a survey of 32 alkyl diazirine probes, we use this reactivity profile to rationalize why alkyl diazirine probes preferentially enrich highly acidic proteins or those embedded in membranes and why probes with a net positive charge tend to produce higher labeling yields in cells and in vitro. These results indicate that alkyl diazirines are an especially effective chemistry for surveying the membrane proteome and will facilitate design and interpretation of biomolecular labeling experiments with diazirines.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.