UDP-4-azido-4-deoxy-D-Glc.2Na

UDP-4-azido-4-deoxy-D-Glc.2Na (Uridine Diphosphate 4-Azido-4-deoxy-D-glucose disodium salt) is a modified nucleotide sugar used in glycosylation research. The incorporation of an azido group at the 4th position of the glucose molecule allows for bioorthogonal labeling techniques and metabolic engineering, particularly in the study of glycan biosynthesis and function.

Structure & Properties:

• Molecular Weight (MW): Approximately 594 g/mol (depending on the specific form)
• Chemical Formula: C15H22N5Na2O16P2 (approximate)
• Synonyms: UDP-4-N3-Glc, UDP-4-azido-4-deoxyglucose disodium salt
• Functional Groups: Features an azido group (-N3) at the 4-position of the glucose ring, making it reactive for click chemistry.

Biological Role:

• Modified Sugar Donor: UDP-4-azido-4-deoxy-D-Glc.2Na acts as a donor of azido-modified glucose in glycosylation processes. The azido group enables selective labeling of glycans in biological systems through bioorthogonal reactions, without affecting native biological functions.
• Role in Glycosylation: This compound is utilized in metabolic labeling to incorporate azido-modified glucose into glycan structures, which can be tagged with reporter molecules for visualization.

Applications:

• Bioorthogonal Chemistry: The azido group in UDP-4-azido-4-deoxy-D-Glc.2Na participates in copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, commonly known as “click chemistry.” This allows for precise labeling and tracking of glycans in cells and tissues.
• Metabolic Labeling of Glycans: The azido-modified glucose can be metabolized by cells and incorporated into glycoproteins and glycolipids, enabling glycan tracking through bioorthogonal reactions.

Significance in Research:

• Glycan Tracking: UDP-4-azido-4-deoxy-D-Glc.2Na is used to study the biosynthesis, function, and turnover of glycans in living systems, providing insights into cellular processes, disease progression, and glycan-mediated interactions.
• Proteomics and Glycomics: This compound aids in research on glycoprotein and glycolipid structures, which are critical for understanding cellular signaling, immune responses, and disease mechanisms.

Key Roles:

• Glycan Labeling: As a metabolic label, UDP-4-azido-4-deoxy-D-Glc.2Na is used for tagging glycans in complex biological environments, facilitating their study in vitro and in vivo.
• Cellular Imaging: It enables live-cell imaging experiments by tagging glycans with fluorescent or other reporter molecules for visualization in biological samples.

Storage and Stability:

• Storage: Store at -20°C in a moisture-free environment.
• Stability: The compound remains stable under proper storage conditions but can degrade if exposed to heat, moisture, or light.

Research Applications:

• Glycobiology: UDP-4-azido-4-deoxy-D-Glc.2Na is widely used in glycan research to label, visualize, and study glycan structures and their biological roles.
• Synthetic Biology: It is also applied in the engineering of synthetic glycans for research, diagnostics, and therapeutic applications, helping to advance the field of glycoscience.

Potential Impact:

• Therapeutic Development: UDP-4-azido-4-deoxy-D-Glc.2Na could be employed in therapeutic strategies targeting glycosylation pathways, which are implicated in diseases such as cancer, immune disorders, and infectious diseases.
• Bioorthogonal Labeling: Its use in click chemistry facilitates the selective labeling of glycan structures, improving the ability to study their biological roles and interactions.

Key Research Areas:

• Cellular Glycosylation: This compound helps researchers investigate glycan biosynthesis and its impact on cellular functions and diseases.
• Glycan Engineering: It is used in the creation of synthetic glycans, offering potential for new therapeutic or diagnostic tools.

Conclusion:

UDP-4-azido-4-deoxy-D-Glc.2Na is a valuable tool in glycobiology research, enabling precise labeling and tracking of glycans in biological systems through bioorthogonal chemistry. It contributes significantly to the understanding of glycan structures, functions, and dynamics, with potential applications in therapeutic development and synthetic biology.