ArticleChembiochem : a European journal of chemical biology2021
Metabolic Glycoengineering with Azide- and Alkene-Modified Hexosamines: Quantification of Sialic Acid Levels.
Article in Chembiochem : a European journal of chemical biology, 2021. 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, 28 citations in OpenAlex.
- Metabolic Glycoengineering Enables Fluorine-18 Radiolabeling of T Lymphocytes via Dual-Bioorthogonal Chemistry.Bioconjugate chemistry · 2026Article
- Site-specific labelling of native peptides and proteins: chemical and enzymatic strategies.Beilstein journal of organic chemistry · 2026Review
- Self-Assembly of Alkynylplatinum(II) Complexes for Sialic Acid Detection and Differentiation of Cancer Cells from Normal Cells.Journal of the American Chemical Society · 2025Article
- Article
- Metabolic Probing of Sialylated Glycoconjugates with Fluorine-Selenol Displacement Reaction (FSeDR).ACS bio & med chem Au · 2025Article
- Protein oxidation of fucose environments (POFE) reveals fucose-protein interactions.Chemical science · 2024Article
- Selenium-based metabolic oligosaccharide engineering strategy for quantitative glycan detection.Nature communications · 2023Article
- Real-time monitoring of the sialic acid biosynthesis pathway by NMR.Chemical science · 2023Article
- Recombinant mucin biotechnology and engineering.Advanced drug delivery reviews · 2023Review
- Clickable Polysaccharides for Biomedical Applications: A Comprehensive Review.Progress in polymer science · 2022Article
- Metabolic Glycan Labeling of Cancer Cells Using Variably Acetylated Monosaccharides.Bioconjugate chemistry · 2022Article
- An Advanced 'clickECM' That Can be Modified by the Inverse-Electron-Demand Diels-Alder Reaction.Chembiochem : a European journal of chemical biology · 2022Article
- Chemical reporters to study mammalian O-glycosylation.Biochemical Society transactions · 2021Review
- Metabolic Glycoengineering with Azide- and Alkene-Modified Hexosamines: Quantification of Sialic Acid Levels.Chembiochem : a European journal of chemical biology · 2021Article
- Metabolic Glycoengineering in hMSC-TERT as a Model for Skeletal Precursors by Using Modified Azide/Alkyne Monosaccharides.International journal of molecular sciences · 2021Article
- Application of the Inverse-Electron-Demand Diels-Alder Reaction for Metabolic Glycoengineering.Frontiers in chemistry · 2021Review
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Metabolic glycoengineering (MGE) is an established method to incorporate chemical reporter groups into cellular glycans for subsequent bioorthogonal labeling. The method has found broad application for the visualization and isolation of glycans allowing their biological roles to be probed. Furthermore, targeting of drugs to cancer cells that present high concentrations of sialic acids on their surface is an attractive approach. We report the application of a labeling reaction using 1,2-diamino-4,5-methylenedioxybenzene for the quantification of sialic acid derivates after MGE with various azide- and alkene-modified ManNAc, GlcNAc, and GalNAc derivatives. We followed the time course of sialic acid production and were able to detect sialic acids modified with the chemical reporter group - not only after addition of ManNAc derivatives to the cell culture. A cyclopropane-modified ManNAc derivative, being a model for the corresponding cyclopropene analog, which undergoes fast inverse-electron-demand Diels-Alder reactions with 1,2,4,5-tetrazines, resulted in the highest incorporation efficiency. Furthermore, we investigated whether feeding the cells with natural and unnatural ManNAc derivative results in increased levels of sialic acids and found that this is strongly dependent on the investigated cell type and cell fraction. For HEK 293T cells, a strong increase in free sialic acids in the cell interior was found, whereas cell-surface sialic acid levels are only moderately increased.
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