Fluorine-modified acetylgalactosamine derivatives—an emerging tool in glycochemistry 120664-90-6

D-Galactopyranose,2-(acetylamino)-2,4-dideoxy-4-fluoro-, 1,3,6-triacetate is a fluorinated sugar derivative with a precise structure, showing unique value in glycochemistry, medicinal chemistry and chemical biology research. By introducing fluorine atoms and acetyl groups at specific sites on the galactose skeleton, this compound achieves fine control of physical and chemical properties and biological activity, becoming an important building block for exploring the functions of sugars and developing new bioactive molecules.

Chemical Information

Chemical name: D-Galactopyranose,2-(acetylamino)-2,4-dideoxy-4-fluoro-, 1,3,6-triacetate

Common name: 2-acetamido-2,4-dideoxy-4-fluoro-1,3,6-tri-O-acetyl-D-galactopyranose

Chemical formula: C14H20FNO8

Molecular weight: 349.31 g/mol

CAS number: 120664-90-6

Category: Fluorinated Compound

Structural features

The design of this molecule incorporates multiple key strategies for glycosyl modification, forming the basis for its unique properties:

Fixed-site introduction of fluorine atoms: At the C-4 position of the sugar ring, the hydrogen atom is replaced by a fluorine atom. Fluorine atoms have strong electronegativity and small atomic radius. Its introduction can significantly change the electron distribution, conformational preference and stability of adjacent glycosidic bonds of the sugar ring. It can also usually enhance the metabolic stability and membrane permeability of the molecule.

Co-modification of amino group and acyl group: The acetamido group at C-2 position provides an important hydrogen bond donor and acceptor site, simulating the structural characteristics of various natural glycosaminoglycans. At the same time, the hydroxyl groups at positions 1, 3, and 6 are completely acetylated. This protection strategy not only improves the stability and lipid solubility of the intermediate, facilitates synthetic operations, but also lays the foundation for its further regioselective functionalization.

Configuration stability: As a derivative of D-galactose, its pyran ring structure and specific stereochemistry provide a precise three-dimensional template for molecular recognition. The introduction of fluorine atoms and acetyl groups is controlled stereoscopically to ensure the clarity and consistency of the product configuration.

Main applications and value

Key intermediates for the development of carbohydrate drugs and probes

Fluorosaccharide compounds have attracted much attention in the development of new drugs. This molecule can serve as an advanced precursor for the synthesis of more complex fluorinated oligosaccharides, glycosides or glycoconjugates. The fluorine atoms in its structure can be used for preliminary research on 18F labeling and have potential in the development of positron emission tomography (PET) imaging probes. In addition, this structure can be used to simulate or interfere with cell surface sugar-protein interactions, providing new ideas for the development of anti-inflammatory, antiviral or anti-tumor drugs.

Basic research tools on glycobiology

In the field of basic research, this compound is an ideal tool molecule for studying the substrate specificity and inhibition mechanism of sugar metabolism enzymes (such as glycosyltransferases, glycoside hydrolases). The introduction of 4-fluorine can often form transition state analogs or irreversible inhibitors of enzymatic reactions, which can be used to analyze the catalytic mechanism of enzymes. Its acetyl-protected form also facilitates various chemical transformations in solution to construct customized sugar chain structures for studying the fine functions of sugars in cell communication and immune recognition.

Building Blocks of Organic Synthesis and Chemical Biology

As a module with multiple differentially deprotected or functionalized sites, this molecule has practical value in the total synthesis of complex natural products and the construction of combinatorial chemical libraries. Chemists can use it for selective modification and systematically study the contribution of different substituents on the sugar ring to biological activity, thereby establishing a structure-activity relationship model and guiding rational drug design.

Conclusion

D-Galactopyranose, 2-(acetylamino)-2,4-dideoxy-4-fluoro-, 1,3,6-triacetate represents a typical example of high-performance modified molecules obtained through rational design in modern glycochemistry. It combines the unique advantages of fluorine chemistry with the three-dimensional complexity of glycochemistry, providing yet another high-value chemical entity for cutting-edge biomedical research, diagnostic tool development, and innovative drug discovery. Its application prospects in multiple interdisciplinary fields are waiting for researchers to further explore and expand.

The above information is provided by the editor of KASONS and is for scientific research only.