ArticleACS chemical biology2017
The Small Molecule 2-Azido-2-deoxy-glucose Is a Metabolic Chemical Reporter of O-GlcNAc Modifications in Mammalian Cells, Revealing an Unexpected Promiscuity of O-GlcNAc Transferase.
Article in ACS chemical biology, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed, 43 citations in OpenAlex.
- Unveiling extracellular matrix assembly: Insights and approaches through bioorthogonal chemistry.Materials today. Bio · 2023Review
- Chemical Biology Approaches to Understanding Neuronal O-GlcNAcylation.Israel journal of chemistry · 2023Article
- Investigation of in vitro histone H3 glycosylation using H3 tail peptides.Scientific reports · 2022Article
- Synthesis and mammalian cell compatibility of light-released glycan precursors for controlled metabolic engineering.Bioorganic & medicinal chemistry · 2022Article
- 4-Deoxy-4-fluoro-GalNAz (4FGalNAz) Is a Metabolic Chemical Reporter of O-GlcNAc Modifications, Highlighting the Notable Substrate Flexibility of O-GlcNAc Transferase.ACS chemical biology · 2022Article
- An Augmented Method for Collecting PLGA Nanoparticles and the Fabrication of 1, 3, 4, 6-Tetra-Frontiers in bioengineering and biotechnology · 2022Article
- Article
- Advances in chemical probing of proteinChemical Society reviews · 2021Review
- Chemical reporters to study mammalian O-glycosylation.Biochemical Society transactions · 2021Review
- Design and Synthesis of Metabolic Chemical Reporters for the Visualization and Identification of Glycoproteins.RSC chemical biology · 2021Article
- Chemistry-Assisted Proteomic Profiling of O-GlcNAcylation.Frontiers in chemistry · 2021Review
- The Metabolic Chemical Reporter AcFrontiers in chemistry · 2021Article
- Mass Spectrometric Method for the Unambiguous Profiling of Cellular Dynamic Glycosylation.ACS chemical biology · 2020Article
- Tools for functional dissection of site-specific O-GlcNAcylation.RSC chemical biology · 2020Review
- Metabolic Labeling for the Visualization and Identification of Potentially O-GlcNAc-Modified Proteins.Current protocols in chemical biology · 2020Article
- Click Chemistry in Proteomic Investigations.Cell · 2020Review
- O-Acetylated Chemical Reporters of Glycosylation Can Display Metabolism-Dependent Background Labeling of Proteins but Are Generally Reliable Tools for the Identification of Glycoproteins.Frontiers in chemistry · 2020Article
- Identifying potentially O-GlcNAcylated proteins using metabolic labeling, bioorthogonal enrichment, and Western blotting.Methods in enzymology · 2019Article
- Azide- and Alkyne-Bearing Metabolic Chemical Reporters of Glycosylation Show Structure-Dependent Feedback Inhibition of the Hexosamine Biosynthetic Pathway.Chembiochem : a European journal of chemical biology · 2018Article
- Synthesis of a Novel Fluorescent Ruthenium Complex with an Appended Ac₄GlcNAc Moiety by Click Reaction.Molecules (Basel, Switzerland) · 2018Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Glycans can be directly labeled using unnatural monosaccharide analogs, termed metabolic chemical reporters (MCRs). These compounds enable the secondary visualization and identification of glycoproteins by taking advantage of bioorthogonal reactions. Most widely used MCRs have azides or alkynes at the 2-N-acetyl position but are not selective for one class of glycoprotein over others. To address this limitation, we are exploring additional MCRs that have bioorthogonal functionality at other positions. Here, we report the characterization of 2-azido-2-deoxy-glucose (2AzGlc). We find that 2AzGlc selectively labels intracellular O-GlcNAc modifications, which further supports a somewhat unexpected, structural flexibility in this pathway. In contrast to the endogenous modification N-acetyl-glucosamine (GlcNAc), we find that 2AzGlc is not dynamically removed from protein substrates and that treatment with higher concentrations of per-acetylated 2AzGlc is toxic to cells. Finally, we demonstrate that this toxicity is an inherent property of the small-molecule, as removal of the 6-acetyl-group renders the corresponding reporter nontoxic but still results in protein labeling.
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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.