ArticleJournal of the American Chemical Society2024
Cu-Catalyzed Azide-Alkyne-Thiol Reaction Forms Ubiquitous Background in Chemical Proteomic Studies.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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14 citing papers in PubMed.
- Advancements and applications of click chemistry in protein labeling and bioconjugation.RSC advances · 2026Review
- A cysteine reactive chloroalkane probe enables HaloTag ligation for downstream chemical proteomics analysis.RSC chemical biology · 2026Article
- Chemical Epigenetics: Small Molecules Targeting Chromatin Modifiers in Disease Modulation.Cell biochemistry and biophysics · 2026Review
- Comprehensive Chemoproteomics Unveils Selective HMG-CoA Synthase 1 Inhibitors for Targeting Mevalonate Metabolism in Cancer.Journal of the American Chemical Society · 2026Article
- Aerobic catabolism of isobutylene byApplied and environmental microbiology · 2026Article
- Article
- Cation-Cation Photosensitization for Protein Ligation and Intracellular Catalysis.Journal of the American Chemical Society · 2026Article
- Article
- One-step labeling with a fluorinated porphyrin-based probe enablesInnovation (Cambridge (Mass.)) · 2025Article
- Identification of Methylglyoxal Reactive Proteins with Photocaged Glycating Agents.Chembiochem : a European journal of chemical biology · 2025Article
- Click-linking: a cell-compatible protein crosslinking method based on click chemistry.Nature communications · 2025Article
- Cation-Cation Photosensitization for Protein Ligation and Intracellular Catalysis.bioRxiv : the preprint server for biology · 2025Article
- Proteome selectivity profiling of photoaffinity probes derived from imidazopyrazine-kinase inhibitors.Communications chemistry · 2025Article
- Improved deconvolution of natural products' protein targets using diagnostic ions from chemical proteomics linkers.Beilstein journal of organic chemistry · 2024Review
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2 authors.
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Abstract
We report here a Cu-catalyzed azide-alkyne-thiol reaction forming thiotriazoles as the major byproduct under widely used bio-orthogonal protein labeling "click" conditions. The development of Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) had a tremendous impact on many biological discoveries. However, the considered chemoselectivity of CuAAC is hampered by the high reactivity of cysteine free thiols, yielding thiotriazole protein conjugates. The reaction byproducts generate false-positive protein hits in functional proteomic studies. The reported detail investigation of conjugates between chemical probes containing terminal alkynes, azide tags, and cell lysates reveals the formation of thiotriazoles, which can be readily detected by in-gel fluorescence scanning or after peptide and protein enrichment by mass spectrometry-based proteomics. In protein level identification and quantification experiments, the produced fluorescent bands or enriched proteins may not result from the important enzymatically driven reaction and can be falsely assigned as hits. This study provides a complete list of the most common background proteins. The knowledge of this previously overlooked reactivity now leads to the introduction of modified CuAAC conditions, which avoids the undesired product formation, diminishes the background, and hence improves the signal-to-noise ratio.
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