UDP-6-Azido-6-deoxy-D-galactose Disodium Salt in Glycosylation Research

Uridine-5'-bisphosphate-D-6-triazagalactose disodium salt is a carefully designed sugar nucleotide analogue, known as a "revolutionary probe" in the field of glycobiology and glycoprotein research. It is not only a core tool for exploring glycosylation, a key link in the life process, but also an indispensable high-value raw material for the development of next-generation bioconjugated drugs (such as antibody-drug conjugates ADC).

Chemical Information

· Chemical name: Uridine-5'-diphosphate-D-6-triazagalactose disodium salt; Uridine 5'-(trihydrodiphosphate), P'-(6-azido-6-deoxy-α-D-galactopyranosyl) ester

· English name:UDP-6-azido-6-deoxy-D-Galactose disodium salt

· Chemical formula: C15H21N5O16P2 · xNa

· Molecular weight: 591.32g/mol (calculated as free acid form)

· CAS number: 868208-96-2

Structural features

UDP-6-azidogalactose is a structural analog of the natural sugar donor UDP-galactose. Its unique features are:

· Highly biocompatible azide group: At carbon position 6 of the galactosyl group, the hydroxyl group is replaced by an azide group. This small and precise modification allows it to retain good recognition and binding capabilities with specific glycosyltransferases while introducing unique chemical reactivity.

· The perfect substrate for "click chemistry": The azide group carried by this molecule can undergo an efficient, specific and rapid [3+2] cycloaddition reaction with molecules containing alkynyl groups (through DBCO, BCN, etc.), which is "click chemistry". This reaction can be performed under mild biocompatible conditions with minimal background interference.

Main applications and advantages

1. Core tools for labeling and tracing glycoproteins and glycans

o Traceless labeling: Utilizing the specificity of glycosyltransferases, azide-tagged galactosyl groups are precisely introduced into specific sites on target glycoproteins or cell surface glycans. Subsequently, highly sensitive fluorescent labeling, biotin labeling, or affinity purification of specific glycoforms is achieved through click chemical reactions with alkyne probes bearing reporter groups.

o Revealed function: Ideal tool for studying the role of galactosylation in cell recognition, signal transduction, immune response, and disease development.

2. Key building blocks for the development of new bioconjugated drugs

o Fixed-site coupling of ADC drugs: In the development of ADC drugs, achieving fixed-site and uniform coupling of small molecule toxins on antibodies is the key to pursuing a higher therapeutic index. By enzymatically introducing galactose azide into the specific sugar chain of the antibody, and then using click chemistry to connect the toxin molecules, precise control of the DAR value can be achieved, significantly improving the stability and efficacy of the ADC.

o Improved pharmacokinetics: The coupling strategy based on click chemistry is highly efficient and has fewer side reactions, which helps to develop biologics with better stability and targeting.

3. Chemical glycobiology and synthetic biology research

o Synthesis of artificial sugar chains: As a sugar donor, it is used to enzymatically synthesize non-natural oligosaccharides or polysaccharides containing azide groups, and is used to construct new biological materials or study the relationship between sugar structure and function.

o Cell surface engineering: Through metabolic sugar engineering technology or enzymatic modification, azide tags are displayed on the surface of living cells, and new functional molecules are installed through click chemistry to achieve precise regulation of cell behavior and provide new strategies for cell therapy.

Conclusion

Uridine-5'-bisphosphate-D-6-triazagalactose disodium salt is not just a chemical molecule, it is a bridge connecting biological discovery and drug innovation. From deciphering complex glycobiological mechanisms to promoting the development of cutting-edge therapies such as ADC and cell therapy, its value has become increasingly prominent.