UDP-6F-α-D-Galactose - an advanced sugar nucleotide substrate enabling glycosylation research

In the cutting-edge fields of glycobiology and glycoprotein drug development, precise regulation of glycosylation is the key to determining drug efficacy and stability. Uridine 5'-(trihydrogen diphosphate), P'-(6-deoxy-6-fluoro-α-D-galactopyranosyl) ester, as a specifically fluorinated modified sugar nucleotide substrate, is becoming a core chemical tool to promote the development of next-generation biological therapies, especially antibody drugs, vaccines and cell therapies, with its unique chemical properties.

Chemical Information

· Chemical name: Uridine 5'-(trihydrogen diphosphate), P'-(6-deoxy-6-fluoro-α-D-galactopyranosyl) ester

· Common name: UDP-6F-α-D-Galactose; fluorouridine diphosphate galactose

· Chemical formula: C15H23FN2O16P2

· Molecular weight: 568.29 g/mol

· CAS number: 736904-78-2

Structural features

This product is an analog of uridine diphosphate galactose. Its excellence lies in its exquisite fluorine atom modification:

· Precise fluorine atom substitution: At carbon position 6 of the galactosyl group, the hydroxyl group is replaced by a fluorine atom. The van der Waals radius of fluorine atom is similar to that of hydrogen atom, but its strong electronegativity can significantly change the electron distribution and conformation of the sugar ring, and can also simulate certain three-dimensional effects of hydroxyl groups.

· Stable high-energy sugar donor: As a sugar molecule activated by uridine diphosphate, it can be recognized by specific glycosyltransferases and used to accurately transfer 6-fluorogalactose groups to proteins, oligosaccharides or other acceptor molecules.

· Enhanced metabolic stability: The introduction of C-F bonds makes it more stable to certain glycoside hydrolases, reducing the risk of premature degradation in biological systems, thus improving its efficiency in research and applications.

Main applications and advantages

1. Key tools for glycoprotein engineering and antibody drug optimization

· Customized sugar chain structure: Researchers can introduce 6-fluorogalactose into the sugar chain of glycoproteins through glycosyltransferase reactions in vitro or in cell systems. This provides a powerful means to study the effects of specific glycosylation modifications on protein folding, stability, immunogenicity and biological activity.

· Enhance the efficacy of therapeutic antibodies: The glycosylation pattern (such as galactosylation level) of the Fc segment of the antibody directly affects its effector functions such as antibody-dependent cell-mediated cytotoxicity. By introducing fluorinated analogs, novel glycoforms can be explored and optimized to develop next-generation antibody drugs with enhanced efficacy.

2. Research probes for enzymatic mechanism and inhibitor development

· Study on the mechanism of glycosyltransferase: It is an ideal probe for studying the substrate specificity, catalytic mechanism and kinetic parameters of the galactosyltransferase family. The introduction of fluorine atoms may change the interaction between enzymes and substrates, providing clues to reveal key structural domains of enzyme functions.

· Potential enzyme inhibitor: As an analog of a natural substrate, it has the potential to competitively inhibit specific glycosyltransferases, showing potential as a lead compound in basic research and even drug development (such as anti-metastasis, anti-inflammatory drugs).

3. chemoenzymatic synthesis of complex oligosaccharides and glycoconjugates

· Efficient synthesis platform: In chemoenzymatic synthesis, this product can be used as a stable glycosylation donor for the efficient and highly selective construction of complex oligosaccharides, glycopeptides or glycolipids containing 6-fluorogalactose. These structurally unique molecules are indispensable raw materials for the development of new vaccines, diagnostic reagents and cell surface signaling research.

4. Research on cell surface modification and interaction

· Regulating intercellular communication: The glycocalyx on the cell surface plays a central role in cell recognition, adhesion, and signal transduction. Introducing fluorinated sugars to the cell surface through metabolic labeling or enzymatic methods can be used to study the specific functions of glycosylation in physiological and pathological processes such as cancer and immune response.

Conclusion

Uridine 5'-(trihydrogen diphosphate), P'-(6-deoxy-6-fluoro-α-D-galactopyranosyl) ester is not just a chemical reagent, it is a key that can accurately control the "sugar-coated code" of life. From unlocking new properties of glycoprotein drugs to mapping complex intercellular communications, its application prospects are extremely broad.