UDP-6-azido-6-deoxy-N-acetyl-D-glucosamine Disodium Salt

UDP-6-azido-6-deoxy-N-acetyl-D-glucosamine Disodium Salt is a synthetic nucleotide sugar derivative commonly used in glycobiology and biochemistry. Here’s a detailed breakdown:

Structure & Properties:

• Molecular Weight (MW): Approximately 676 g/mol (depending on the specific form)
• Chemical Formula: C17H25N6Na2O16P2
• Synonyms: UDP-6-N3-GlcNAc
• Functional Groups: The structure includes an azido group (-N3) at the 6th position of the glucosamine ring, a modification from the hydroxyl group (-OH), and an acetyl group (-COCH3) on the amino group at position 2.

Biological Role:

• Biosynthesis Pathway: UDP-6-azido-6-deoxy-GlcNAc is synthesized by modifying UDP-N-acetylglucosamine (UDP-GlcNAc) through enzymatic or chemical processes, replacing the hydroxyl group at the 6-position with an azido group.
• Function: This molecule serves as a sugar donor in glycosylation reactions, particularly in metabolic labeling and bioorthogonal chemistry. The azido group allows for site-specific modifications via click chemistry reactions, enabling the attachment of fluorescent tags, biotin, or other molecules.

Applications:

• Glycan Labeling: The azido group allows for the incorporation of UDP-6-N3-GlcNAc into glycans for metabolic labeling and detection.
• Bioorthogonal Chemistry: It enables site-specific conjugation through azide-alkyne cycloaddition (“click chemistry”) for downstream applications in proteomics, glycomics, and diagnostics.
• Cellular Glycan Engineering: Used in glycobiology research to manipulate and visualize glycan structures within cells.

Significance in Research:

• Glycan Imaging: UDP-6-N3-GlcNAc is used in experiments aimed at visualizing glycosylation patterns in cells through metabolic labeling followed by azide-specific detection.
• Synthetic Glycan Development: It helps in the synthesis of modified glycans with applications in vaccine development, drug delivery systems, and targeted therapies.

Storage and Stability:

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

Research Applications:

• Glycan Metabolic Labeling: UDP-6-N3-GlcNAc is a powerful tool for tracking and analyzing glycan biosynthesis and modification in live cells.
• Therapeutic Research: Investigating the role of azido-modified glycans in immunomodulation and targeted drug delivery.

Potential Impact:

• Glycan Engineering: The ability to modify glycans site-specifically has broad implications for synthetic biology, enabling the design of glycoproteins with tailored functions.
• Therapeutics and Diagnostics: The use of click chemistry with UDP-6-N3-GlcNAc in therapeutic targeting and diagnostics is being explored for its potential in treating diseases like cancer and autoimmune disorders.

This synthetic nucleotide sugar is a versatile tool in both basic and applied research, particularly in fields involving glycosylation and carbohydrate chemistry