A Fluorinated Azido Sugar for Chemical Biology and Drug Discovery
2-Acetamido-6-azido-2,3,6-trideoxy-3-fluoro-D-galactopyranose combines a fluorine substituent with an azide handle for studies in glycoengineering, drug design, and bioorthogonal chemistry.
2-Acetamido-6-azido-2,3,6-trideoxy-3-fluoro-D-galactopyranose combines a fluorine substituent with an azide handle for studies in glycoengineering, drug design, and bioorthogonal chemistry.
Chemical information
Chemical name: 2-Acetamido-6-azido-2,3,6-trideoxy-3-fluoro-D-galactopyranose. Common description: Fluorinated azido galactose derivative. Molecular formula: C₈H₁₃FN₄O₄. Molecular weight: 248.21 g/mol. Classification: Fluorinated compound.
Structural features
The C3 fluorine can change conformation, electron distribution, and receptor interactions. The carbon–fluorine bond can also affect metabolic stability. At C6, the azide group provides a handle for bioorthogonal coupling, for example by copper-catalyzed azide–alkyne cycloaddition. The C2 acetamido group is a feature shared with natural amino sugars and may help retain elements of their recognition profile.
Applications
Glycoprotein and glycoconjugate synthesis
This fluorinated analogue can be explored as an intermediate for glycopeptides, glycoproteins, and glycolipids. Fluorine substitution can probe stereoelectronic effects and susceptibility to enzymatic degradation in studies of how glycans influence protein function.
Bioorthogonal labeling and cell-surface engineering
The azide group can be used to attach fluorophores, drugs, or other functional molecules. If incorporation is established in a given metabolic glycoengineering system, click labeling can enable visualization or targeting of cell-surface glycoconjugates.
Enzymology and inhibitor design
As a potential substrate analogue, the compound can be used to investigate glycosidases and glycosyltransferases. The C3 fluorine can help probe enzyme–substrate interactions and guide early inhibitor design.
Drug conjugation and targeted delivery
The azide can provide a conjugation point for linkers or targeting groups in studies of antibody–drug conjugates and other targeted molecules. The galactose scaffold may also be investigated for recognition by particular lectins or carbohydrate-binding receptors.
Conclusion
Combining fluorine with an azide in one sugar provides distinct handles for studying recognition, labeling, conjugation, and enzyme activity.
Prepared by KASONS. For research use only.