129728-87-6—A key building block in fluorinated sugar chemistry

2-acetamido-2,4-dideoxy-4-fluoro-A-D-glucopyranose is a fluorinated sugar derivative with important research value. As a key structural building block in the fields of glycochemistry and medicinal chemistry, it provides a unique chemical tool for developing new bioactive molecules and exploring the mechanism of carbohydrate metabolism.

Chemical Information

Chemical name: 2-acetamido-2,4-dideoxy-4-fluoro-α-D-glucopyranose

Common name: 2-acetamido-2,4-dideoxy-4-fluoro-α-D-glucose

English name: 2-ACETAMIDO-2,4-DIDEOXY-4-FLUORO-ALPHA-D-GLUCOPYRANOSE

Chemical formula: C8H14FNO5

Molecular weight: 223.2 g/mol

CAS number: 129728-87-6

Category: Fluorinated Compound

Structural features

This molecule is a specifically fluorinated and deoxy-modified derivative of glucose. Its structure has the following salient features:

Fluorine atom substitution: On the carbon atom at position 4 of the sugar ring, the hydrogen atom is replaced by a fluorine atom. The introduction of fluorine atoms, due to its high electronegativity and small atomic radius, can significantly change the electron distribution, conformational stability and interaction mode of the sugar ring with biological targets without causing obvious steric hindrance.

Specific deoxygenation and modification: The molecule is in a deoxygenated state at positions 2 and 4, and an acetylamino group is connected to position 2. This combination of modifications eliminates hydroxyl groups at specific positions, altering the hydrogen-bonding network and hydrophilicity of the molecule, while the acetylamino group provides an amide bond that can serve as a recognition or interaction site.

Clear configuration: The clear configuration of Alpha-D-glucopyranose ensures its specificity in biological system research, allowing it to simulate or interfere with the metabolism and recognition process of natural sugar substances.

Main applications and advantages

Glycosylation inhibitors and metabolic research tools

As a precisely designed sugar analogue, this compound can be used to study sugar metabolic pathways, particularly those involving glucosamine or related amino sugars. The introduction of 4-fluoro often enables it to irreversibly or potently inhibit specific glycosidases or glycosyltransferases, thereby becoming an effective probe for studying complex glycobiological processes, such as protein glycosylation, cell signaling, and pathogen-host interactions.

Lead structures for new drug development

Fluorinated Compound is favored in drug design. The fluorinated sugar structure can be used as a lead compound for the development of antiviral, antibacterial or antitumor drugs. For example, key biological processes such as virus or bacterial cell wall synthesis and glycoprotein processing often rely on specific sugar metabolism enzymes, and such modified sugars can serve as substrate analogs to interfere with these processes. Its unique structure provides a starting point for optimizing pharmacodynamic properties (such as target affinity) and pharmacokinetic properties (such as metabolic stability).

Chemical biology and probe synthesis

In the field of chemical biology, this molecule is a valuable intermediate for the synthesis of active site-directed probes or fluorescently labeled probes. The acetylamino group can serve as a site for further chemical coupling, while the fluorine atom can serve as a natural label for ¹⁹F nuclear magnetic resonance (NMR) studies, which can be used to monitor metabolic fate or target binding in organisms in real time without interference background.

Carbohydrate chemical synthesis building blocks

It is a versatile synthetic building block for synthetic chemists. Can be used to construct more complex oligosaccharides, glycoconjugates or natural product analogs. The presence of fluorine atoms can guide the regioselectivity and stereoselectivity of subsequent reactions, providing new strategies for the synthesis of challenging sugar-containing molecular structures.

Conclusion

2-acetamido-2,4-dideoxy-4-fluoro-A-D-glucopyranose represents a finely designed molecule in fluorinated sugar chemistry. By combining fluorine atoms with specific deoxygenation and amino modifications, a tool molecule with unique physicochemical and biological properties within a biocompatible framework is created. From the elucidation of the mechanism of basic life processes to the discovery and development of new sugar-based drugs, this compound has demonstrated important potential as a core research material and starting point for innovation, continuing to promote the progress of sugar science and related therapeutic fields.

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