CAS 149033-47-6: A Fluorinated Glucose Analogue for Glycosylation Research
2-Acetamido-3-fluoro-2,3-dideoxy-D-glucopyranose is a fluorinated amino sugar for studies of carbohydrate recognition, glycosylation enzymes, and the synthesis of glycoconjugates and other analogues.
2-Acetamido-3-fluoro-2,3-dideoxy-D-glucopyranose is a fluorinated carbohydrate used in research on sugar chemistry and glycobiology. It provides a defined scaffold for investigating interactions between carbohydrates and biomolecules, designing enzyme probes, and exploring carbohydrate-based lead compounds.
Chemical information
• Chemical and common name: 2-acetamido-3-fluoro-2,3-dideoxy-D-glucopyranose
• CAS number: 149033-47-6
• Molecular formula: C₈H₁₄FNO₅
• Molecular weight: 223.20 g/mol
• Classification: Fluorinated compound
Structural features
At C-3, fluorine replaces the hydroxyl group. Fluorine is small and strongly electronegative, making the substitution useful for probing how the steric and electronic properties of this position affect sugar conformation and metabolism.
The sugar is deoxygenated at C-2 and C-3. Its C-2 acetamido group is a feature shared with N-acetylglucosamine (GlcNAc), making this analogue relevant to studies of GlcNAc recognition and metabolism. Fluorine may influence neighboring bonds and weak polar interactions with proteins. These effects can be studied to understand whether a modified sugar acts as a metabolic antagonist or a stable mimic.
Research applications
1. Glycosylation and carbohydrate-processing enzymes
Glycosidases and glycosyltransferases play key roles in biological processes. This analogue can be evaluated as a probe or inhibitor candidate in studies of those enzymes. Comparing its binding and reactivity with those of natural substrates can help clarify enzyme mechanisms and inform research on inhibitors relevant to infection and metabolic disease.
2. Synthesis of carbohydrate-based research compounds
A defined fluorinated building block can be incorporated into more complex carbohydrate analogues, nucleoside analogues, or glycoconjugates. These derivatives can help researchers test how fluorination affects activity, selectivity, metabolic stability, membrane permeability, and pharmacokinetic properties.
3. Chemical glycobiology and molecular probes
The scaffold can be used to explore recognition of glycoproteins and biological functions of the cell-surface glycocalyx. It can also be evaluated as a precursor for metabolic labeling probes that track carbohydrate pathways in cells. The fluorinated structure offers a way to study how resistance to enzymatic hydrolysis affects probe behavior.
Conclusion
This C-3 fluorinated glucose analogue provides a tool for probing glycan recognition and metabolism and for building structurally defined derivatives. It supports basic studies of carbohydrate function as well as exploratory research on carbohydrate-based drug candidates.
Prepared by KASONS. For research use only.