2-Acetamido-6-azido-3-fluoro-2,3,6-trideoxy-D-glucopyranose for Glycobiology and Click Chemistry
This fluorinated D-glucose derivative combines a C-3 fluorine substituent with a C-6 azide handle. It is a building block for glycobiology research, molecular probe design, and bioorthogonal conjugation.
2-Acetamido-6-azido-3-fluoro-2,3,6-trideoxy-D-glucopyranose is a functionalized sugar derivative. It combines carbohydrate stereochemistry with the electronic effects of fluorine and the reactivity of an azide group, making it a building block and tool compound for medicinal chemistry and chemical biology.
Chemical information
• Chemical name: 2-acetamido-6-azido-3-fluoro-2,3,6-trideoxy-D-glucopyranose
• Molecular formula: C₈H₁₃FN₄O₄
• Calculated molar mass: 248.21 g/mol
• Classification: Fluorinated compound
Structural features
Fluorine at C-3. Fluorine can affect electron distribution, conformation, and interactions with biomolecules. Its introduction can also change metabolic stability.
Azide at C-6. The azide is a handle for click chemistry. Copper-catalyzed azide–alkyne cycloaddition can join the sugar to alkyne-bearing partners for bioconjugation, probe labeling, or polymer modification.
Modified sugar scaffold. Replacing hydroxyl groups at C-2, C-3, and C-6 changes the polarity and may affect the conformational behavior and binding of the sugar. The C-2 acetamido group can donate and accept hydrogen bonds, retaining features of naturally occurring amino sugars.
Defined stereochemistry. The chiral centers of the D-glucopyranose scaffold help determine how the derivative interacts with biological targets.
Research applications
1. Building block for medicinal chemistry
Fluorination can be used to study how changes in lipophilicity, membrane permeability, metabolism, and target binding affect lead compounds. This derivative provides a starting point for research on glycomimetics, enzyme inhibitor candidates, and carbohydrate-containing analogues.
2. Chemical biology and probe design
The azide enables bioorthogonal attachment of fluorescent groups, biotin, or other affinity tags to suitably designed glycans, nucleosides, or related molecules. These probes can help researchers trace biosynthetic pathways, investigate protein–carbohydrate interactions, or explore live-cell imaging. The fluorine substituent can also serve as a reporter in fluorine-19 NMR experiments.
3. Glycobiology
The compound provides a scaffold for investigating carbohydrate metabolism, recognition, and function. Related analogues can be evaluated in cellular systems to probe the effects of particular glycosylation changes or to study processes that depend on natural sugar substrates.
4. Synthetic intermediate
The azide and acetamido groups offer starting points for further functionalization. Reduction of the azide, followed by reactions such as alkylation or acylation where appropriate, can produce amines, amides, and other derivatives for fluorinated sugar libraries.
Conclusion
This functionalized fluorinated sugar brings together the electronic effects of fluorine, the coupling versatility of an azide, and the biological relevance of a carbohydrate scaffold. It is a tool for molecular probe design, mechanistic studies of carbohydrates, and exploratory medicinal chemistry.
Prepared by KASONS. For research use only.