Exploring the Potential of Norbornene-Modified Mannosamine Derivatives for Metabolic Glycoengineering
| Autor: | Ellen Batroff, Anne-Katrin Späte, Oliver R. Baudendistel, Valentin Wittmann, Jeremias E. G. A. Dold, Verena F. Schart, Daniel E. Wieland |
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| Rok vydání: | 2016 |
| Předmět: |
Glycan
Cell Membrane Permeability Stereochemistry Stereoisomerism Bioengineering Phenylenediamines 010402 general chemistry 01 natural sciences Biochemistry chemistry.chemical_compound Polysaccharides Humans carbohydrates Diels–Alder reaction metabolic engineering norbornenes sialic acids Molecular Biology Norbornene Microscopy Confocal biology 010405 organic chemistry Organic Chemistry Mannosamine Hexosamines Flow Cytometry Norbornanes Cycloaddition N-Acetylneuraminic Acid 0104 chemical sciences Sialic acid Kinetics HEK293 Cells chemistry ddc:540 biology.protein Molecular Medicine Bioorthogonal chemistry N-Acetylneuraminic acid |
| Zdroj: | Chembiochem : a European journal of chemical biology. 17(14) |
| ISSN: | 1439-7633 |
| Popis: | Metabolic glycoengineering (MGE) allows the introduction of unnaturally modified carbohydrates into cellular glycans and their visualization through bioorthogonal ligation. Alkenes, for example, have been used as reporters that can react through inverse-electron-demand Diels-Alder cycloaddition with tetrazines. Earlier, norbornenes were shown to be suitable dienophiles; however, they had not previously been applied for MGE. We synthesized two norbornene-modified mannosamine derivatives that differ in the stereochemistry at the norbornene (exo/endo linkage). Kinetic investigations revealed that the exo derivative reacts more than twice as rapidly as the endo derivative. Through derivatization with 1,2-diamino-4,5-methylenedioxybenzene (DMB) we confirmed that both derivatives are accepted by cells and incorporated after conversion to a sialic acid. In further MGE experiments the incorporated sugars were ligated to a fluorophore and visualized through confocal fluorescence microscopy and flow cytometry. published |
| Databáze: | OpenAIRE |
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