UDP-6-azido-6-deoxy-D-Glc.2Na

UDP-6-azido-6-deoxy-D-Glc.2Na (Uridine Diphosphate 6-Azido-6-deoxy-D-glucose disodium salt) is a modified nucleotide sugar that plays a crucial role in glycosylation research, particularly in the development of bioorthogonal labeling and metabolic engineering of glycans. The introduction of an azido group at the 6th position of the glucose ring makes this compound an important tool in studying carbohydrate functions and interactions.

Structure & Properties:

• Molecular Weight (MW): Approximately 594 g/mol (depending on the specific form)
• Chemical Formula: C15H22N5Na2O15P2 (approximate)
• Synonyms: UDP-6-N3-Glc, UDP-6-azido-6-deoxyglucose disodium salt
• Functional Groups: It contains an azido group (-N3) at the 6-position of the glucose ring, which is reactive and can participate in click chemistry reactions.

Biological Role:

• Modified Sugar Donor: UDP-6-azido-6-deoxy-D-Glc.2Na serves as a donor of azido-modified glucose in glycosylation reactions. The azido group enables selective and covalent modifications through bioorthogonal reactions, without interfering with native biological processes.
• Role in Glycosylation: This compound is widely used in metabolic labeling experiments to track and study glycans in living cells and tissues.

Applications:

• Bioorthogonal Chemistry: The azido group on UDP-6-azido-6-deoxy-D-Glc.2Na reacts selectively with alkyne-containing molecules in copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. This reaction, commonly referred to as “click chemistry,” allows for the precise labeling and visualization of glycans in cells.
• Metabolic Labeling of Glycans: Cells can metabolize UDP-6-azido-6-deoxy-D-Glc.2Na into glycoproteins and glycolipids, incorporating the azido-modified sugar into their glycan structures. These modified glycans can then be labeled with fluorescent or other reporter molecules via click chemistry.

Significance in Research:

• Glycan Tracking: The azido group in UDP-6-azido-6-deoxy-D-Glc.2Na enables specific labeling and tracking of glycans in living cells, providing insights into glycan function and turnover in various biological processes, including cell signaling, development, and disease.
• Proteomics and Glycomics: This compound is used in glycoprotein and glycolipid research, facilitating the study of glycosylation patterns and their role in cellular processes and diseases such as cancer, inflammation, and immune responses.

Key Roles:

• Glycan Labeling: UDP-6-azido-6-deoxy-D-Glc.2Na is integral to the metabolic labeling of glycans, enabling researchers to selectively tag and study glycosylated proteins and lipids in complex biological systems.
• Cellular Imaging: It is commonly used in live-cell imaging experiments, allowing for the visualization of glycan distribution and dynamics within cells and tissues.

Storage and Stability:

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

Research Applications:

• Glycobiology: UDP-6-azido-6-deoxy-D-Glc.2Na is extensively used in glycobiology research for labeling and tracking glycan structures in vivo.
• Synthetic Biology: It is employed in the engineering of cells and organisms for the study and manipulation of glycosylation pathways, with potential therapeutic and diagnostic applications.

Potential Impact:

• Therapeutic Development: The ability to modify and track glycans with UDP-6-azido-6-deoxy-D-Glc.2Na could lead to new therapeutic approaches targeting glycosylation pathways in diseases such as cancer, infectious diseases, and autoimmune disorders.
• Bioorthogonal Labeling: This compound facilitates the development of advanced labeling techniques for studying glycan function in real-time, which could improve our understanding of cellular processes and disease mechanisms.

Key Research Areas:

• Cellular Glycosylation: UDP-6-azido-6-deoxy-D-Glc.2Na is critical in studying the glycosylation of proteins and lipids, revealing their roles in cellular signaling, development, and disease.
• Glycan Engineering: Research into the use of azido-modified sugars helps to develop engineered glycans for therapeutic or diagnostic purposes.

Conclusion:

UDP-6-azido-6-deoxy-D-Glc.2Na is a powerful tool in glycosylation research, enabling the precise labeling and tracking of glycans through bioorthogonal chemistry. Its role in the study of glycan functions, interactions, and dynamics in living cells is critical for advancing our understanding of complex biological processes and developing novel therapeutic approaches.