CAS: 189225-37-4: Key nucleotide substrates for glycobiology research and glycosylation engineering

UDP-2-fluoro-2-deoxy-D-galactosamine disodium salt is a specifically modified uridine diphosphate sugar derivative and belongs to the important biomolecule category SugarNucleotides. As indispensable active donor substrates in glycosylation reactions catalyzed by glycosyltransferases, these compounds play an irreplaceable role in basic research on glycobiology, biosynthesis of glycoproteins and glycosaminoglycans, and related drug development.

Chemical Information

Chemical name: Uridine-5'-bisphosphate-2-fluoro-2-deoxy-D-galactosamine disodium salt

Common name: UDP-2-F-D-galactosamine disodium salt

Chemical formula: C15H24FN2NaO16P2

Molecular weight: 592.29 g/mol

CAS number: 189225-37-4

Category: Sugar Nucleotides

Structural features

The structure of UDP-2-fluoro-2-deoxy-D-galactosamine disodium salt combines the classic uridine diphosphate sugar skeleton with precise chemical modification. Its characteristics are mainly reflected in:

l Active sugar donor core: The molecule is composed of uridine monophosphate (UMP) connected to the modified sugar moiety through a pyrophosphate bond, forming the standard recognition and utilization structure of glycosyltransferase.

l Key site modification: At position 2 of the sugar ring, a fluorine atom (-F) is introduced and the hydroxyl group (-OH) is removed at the same time to form a 2-fluoro-2-deoxy structure. The introduction of fluorine atoms, with its strong electronegativity and similar atomic radius, can significantly change the electron distribution and conformation of the sugar ring, and often enhances its metabolic stability against enzyme degradation.

l Galactosamine skeleton: The glycosyl part is D-galactosamine, which is the basic building block of a variety of important glycoconjugates (such as heparin, chondroitin sulfate). Its amino group can provide a site for further sulfonation or acetylation modification.

l Sodium salt form: Provided in the form of disodium salt, which ensures good solubility of the compound in an aqueous buffer system and facilitates the application of in vitro biochemical experiments.

Main applications and advantages

1. Key tools for glycosylation mechanism research and enzymatic analysis

As a modified reactive sugar substrate, UDP-2-fluoro-2-deoxy-D-galactosamine disodium salt is a valuable tool for exploring the substrate specificity, catalytic mechanisms, and kinetic parameters of glycosyltransferases, especially enzymes acting on galactosamine or related derived sugars. The substitution of 2-fluorine may make the molecule a mechanism inhibitor of certain glycosyl hydrolases or glycosyltransferases, which can be used to capture enzyme-substrate intermediates and analyze reaction pathways.

2. Research on glycosaminoglycan (GAG) biosynthesis and engineering

This compound is a mimic or probe for studying key steps in the biosynthetic pathway of glycosaminoglycans such as heparin, heparan sulfate, and chondroitin sulfate. By incorporating it into in vitro synthesis systems or cell culture models, the function of specific glycosyl transfer steps can be studied, or through metabolic oligosaccharide engineering strategies, analogues with chemical reporter groups can be introduced into cell surface glycoconjugates to achieve visualization and functional intervention of sugar chains.

3. Potential molecules for the development of novel therapeutic strategies

Based on its structural characteristics, UDP-2-fluoro-2-deoxy-D-galactosamine disodium salt and its derivatives have potential value in drug development. For example, they could serve as lead compounds for designing inhibitors of sugar synthase enzymes that target specific pathogens, such as bacteria or parasites that utilize unique glycosylation pathways. In addition, in cancer or inflammatory diseases, aberrant glycosylation is an important feature, and this compound can be used to explore strategies to modulate specific glycosylation patterns to intervene in disease processes.

4. Special substrate for chemoenzymatic synthesis of complex sugar chains

In the field of chemoenzymatic synthesis, glycosyltransferases are widely used because of their high regio- and stereoselectivity. The modified sugar nucleotide can be used as a stable donor substrate for the efficient and precise synthesis of oligosaccharide chains or glycoconjugates containing 2-deoxy-2-fluoro-galactosamine structures in vitro. These structures may be rare or difficult to obtain in natural products and are crucial for structure-activity relationship studies.

Conclusion

UDP-2-fluoro-2-deoxy-D-galactosamine disodium salt represents an elegant example in the field of chemical modification of sugar nucleotides. Its unique fluorination and deoxy-modified structure not only provides a powerful molecular probe for in-depth understanding of glycosylation, a core process of life, but also provides researchers engaged in glycobiology, enzymology, glycomedicine chemistry and synthetic biology with key building blocks for constructing complex biomolecules and exploring new therapeutic targets. As the understanding of the role of glycoscience in health and disease continues to deepen, such carefully designed tool molecules will continue to promote the advancement and application exploration of related cutting-edge science.

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