UDP -2-alkyne-GalNAc

UDP-2-Alkyne-GalNAc (Uridine Diphosphate 2-Alkyne-N-Acetylgalactosamine) is a modified nucleotide sugar that plays a significant role in bioorthogonal chemistry and glycosylation research. It consists of uridine diphosphate (UDP) linked to N-acetylgalactosamine (GalNAc), where the 2-position of the sugar ring is modified with an alkyne group. This modification makes it particularly useful in click chemistry applications.

Structure & Properties:

• Molecular Weight (MW): Approximately 645 g/mol (depending on specific modifications)
• Chemical Formula: C18H29N3O17P2 (approximate)
• Synonyms: UDP-2-Alkyne-N-Acetylgalactosamine
• Functional Groups: The key functional group in UDP-2-Alkyne-GalNAc is the alkyne moiety at the 2-position of the GalNAc sugar, which enables bioorthogonal reactions such as click chemistry.

Biological Role:

• Biosynthesis Pathway: UDP-2-Alkyne-GalNAc is synthetically derived and used as a glycosyl donor in various biochemical reactions. It mimics natural UDP-GalNAc but contains the alkyne modification for special applications.
• Function: This modified sugar nucleotide is used in glycosylation reactions where the alkyne group can be conjugated to azide-labeled molecules using click chemistry. It is especially useful in labeling and tracking glycoproteins and glycoconjugates in living systems.

Applications:

• Click Chemistry: UDP-2-Alkyne-GalNAc is widely used in bioorthogonal click chemistry reactions, allowing for specific and efficient labeling of glycoconjugates without interfering with biological processes.
• Glycoprotein Labeling: It enables the tagging of glycoproteins with fluorescent dyes, biotin, or other probes for visualization, isolation, or further study in biochemical and cellular contexts.

Significance in Research:

• Bioorthogonal Labeling: The alkyne group in UDP-2-Alkyne-GalNAc allows for selective, bioorthogonal labeling of glycans, which can then be detected and quantified through azide-alkyne cycloaddition (a click chemistry reaction).
• Glycosylation Studies: This molecule is valuable for studying glycosylation patterns in cells and tissues, helping researchers understand glycan functions in health and disease.

Key Roles:

• Bioconjugation: UDP-2-Alkyne-GalNAc enables bioconjugation through click chemistry, allowing for the study of glycan-protein interactions, tracking of glycosylated molecules, and other glycomics-related research.
• Metabolic Labeling: It is also used in metabolic labeling experiments, where cells incorporate the alkyne-modified sugar into glycoconjugates, which can then be detected via click chemistry.

Storage and Stability:

• Storage: UDP-2-Alkyne-GalNAc should be stored at -20°C in a moisture-free environment for optimal stability.
• Stability: The compound remains stable under these conditions but may degrade when exposed to heat, moisture, or light.

Research Applications:

• Glycomics: UDP-2-Alkyne-GalNAc is extensively used in glycomics for labeling and studying glycan structures, particularly in complex glycoproteins and glycolipids.
• Synthetic Biology: In synthetic biology, it is employed to engineer cells that produce labeled glycans, aiding in the visualization and study of cellular glycosylation pathways.

Potential Impact:

• Therapeutic Glycoconjugates: The ability to label and modify glycans with UDP-2-Alkyne-GalNAc opens up avenues for the development of therapeutic glycoconjugates that can be tracked or targeted within biological systems.
• Diagnostics: This molecule is also useful in the development of diagnostic tools, where glycan structures are labeled and detected in various diseases, including cancer and immune disorders.

Key Research Areas:

• Bioorthogonal Chemistry: Research using UDP-2-Alkyne-GalNAc focuses on developing and optimizing bioorthogonal labeling techniques for studying glycoconjugates.
• Glycoproteomics: This molecule contributes to advances in glycoproteomics, where the goal is to map and understand the glycosylation patterns of proteins in health and disease.

Conclusion:

UDP-2-Alkyne-GalNAc is a modified nucleotide sugar that plays a pivotal role in glycosylation research and bioorthogonal chemistry. Its ability to participate in click chemistry reactions makes it an invaluable tool for labeling and studying glycoproteins, glycolipids, and other glycoconjugates. This molecule is widely used in research applications ranging from metabolic labeling to the development of therapeutic glycans and diagnostic tools, contributing significantly to advances in glycomics and synthetic biology