ArticleBioconjugate chemistry2014
Monitoring dynamic glycosylation in vivo using supersensitive click chemistry.
Article in Bioconjugate chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
30 citing papers in PubMed, 88 citations in OpenAlex.
- inCu-click: DNA-enhanced ligand enables live-cell, intracellular click chemistry reaction with copper catalyst.Nature communications · 2025Article
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- Bioorthogonal chemistry of polyoxometalates - challenges and prospects.Chemical science · 2024Review
- Incorporating, Quantifying, and Leveraging Noncanonical Amino Acids in Yeast.Methods in molecular biology (Clifton, N.J.) · 2022Article
- Article
- A Not-So-Ancient Grease History: Click Chemistry and Protein Lipid Modifications.Chemical reviews · 2021Review
- Artificial Organelles: Towards Adding or Restoring Intracellular Activity.Chembiochem : a European journal of chemical biology · 2021Review
- Bioorthogonal Reactions in Activity-Based Protein Profiling.Molecules (Basel, Switzerland) · 2020Review
- Differential Labeling of Glycoproteins with Alkynyl Fucose Analogs.International journal of molecular sciences · 2020Article
- Tailored therapeutics based on 1,2,3-1MedChemComm · 2019Review
- Recent progress in enzymatic protein labelling techniques and their applications.Chemical Society reviews · 2018Review
- Achieving Controlled Biomolecule-Biomaterial Conjugation.Chemical reviews · 2018Review
- Chemical glycomics enrichment: imaging the recycling of sialic acid in living cells.Journal of inherited metabolic disease · 2018Article
- A One-Step Chemoenzymatic Labeling Strategy for Probing Sialylated Thomsen-Friedenreich Antigen.ACS central science · 2018Article
- Engineered Glycocalyx Regulates Stem Cell Proliferation in Murine Crypt Organoids.Cell chemical biology · 2018Article
- Sialyltransferase-Based Chemoenzymatic Histology for the Detection of N- and O-Glycans.Bioconjugate chemistry · 2018Article
- Profiling of Protein O-GlcNAcylation in Murine CD8ACS chemical biology · 2017Article
- A Chemoenzymatic Histology Method for O-GlcNAc Detection.Chembiochem : a European journal of chemical biology · 2017Article
- AnThe Journal of biological chemistry · 2017Article
- Visualizing glycans on single cells and tissues-Visualizing glycans on single cells and tissues.Current opinion in chemical biology · 2017Review
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
To monitor the kinetics of biological processes that take place within the minute time scale, simple and fast analytical methods are required. In this article, we present our discovery of an azide with an internal Cu(I)-chelating motif that enabled the development of the fastest protocol for Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) to date, and its application toward following the dynamic process of glycan biosynthesis. We discovered that an electron-donating picolyl azide boosted the efficiency of the ligand-accelerated CuAAC 20-38-fold in living systems with no apparent toxicity. With a combination of this azide and BTTPS, a tris(triazolylmethyl)amine-based ligand for Cu(I), we were able to detect newly synthesized cell-surface glycans by flow cytometry using as low as 1 nM of a metabolic precursor. This supersensitive chemistry enabled us to monitor the dynamic glycan biosynthesis in mammalian cells and in early zebrafish embryogenesis. In live mammalian cells, we discovered that it takes approximately 30-45 min for a monosaccharide building block to be metabolized and incorporated into cell-surface glycoconjugates. In zebrafish embryos, the labeled glycans could be detected as early as the two-cell stage. To our knowledge, this was the first time that newly synthesized glycans were detected at the cleavage period (0.75-2 hpf) in an animal model using bioorthogonal chemistry.
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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.