CMP-Neu5Az

CMP-Neu5Az (Cytidine Monophosphate N-Azidoacetylneuraminic Acid) is a modified sialic acid nucleotide commonly used in glycosylation research, particularly for bioorthogonal labeling and metabolic engineering of sialic acids. It contains an azido group (-N3) in place of the acetyl group at the N-acyl position of the Neu5Ac (N-acetylneuraminic acid), allowing for selective tagging in biological systems.

Structure & Properties:

• Molecular Weight (MW): Approximately 634 g/mol (depending on the specific form)
• Chemical Formula: C20H29N6O15P2 (approximate)
• Synonyms: CMP-Neu5Az, CMP-N-azidoacetylneuraminic acid
• Functional Groups: The azido group (-N3) at the N-acyl position of Neu5Ac allows for bioorthogonal reactions such as click chemistry.

Biological Role:

• Modified Sialic Acid Donor: CMP-Neu5Az acts as a donor of azido-modified sialic acid in sialylation reactions, incorporating Neu5Az into glycans, including glycoproteins and glycolipids.
• Role in Glycosylation: This molecule participates in the modification of glycan structures via sialylation, especially in cells engineered to metabolically incorporate Neu5Az into glycosylated proteins and lipids.

Applications:

• Bioorthogonal Labeling: CMP-Neu5Az’s azido group enables specific labeling of sialylated glycans using bioorthogonal click chemistry techniques, aiding in the visualization of sialylated molecules.
• Metabolic Glycoengineering: CMP-Neu5Az is used in metabolic glycoengineering to introduce azide-functionalized sialic acids into cell surface glycans, facilitating studies of glycan dynamics and function.

Significance in Research:

• Glycan Labeling and Visualization: CMP-Neu5Az enables the tracking and study of sialylated glycans in cells and tissues, making it a valuable tool in understanding cellular glycosylation patterns.
• Sialylation Dynamics: Researchers use CMP-Neu5Az to explore the role of sialylation in various biological processes, such as cancer, immune modulation, and pathogen interactions.

Key Roles:

• Sialylation Tracking: CMP-Neu5Az facilitates the incorporation of azido-modified sialic acids into glycans, allowing for the detection and visualization of sialylated glycoconjugates.
• Cellular Imaging: CMP-Neu5Az is widely used in live-cell imaging to study the distribution and function of sialylated glycans in real time.

Storage and Stability:

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

Research Applications:

• Glycobiology: CMP-Neu5Az is used to study glycan structure, biosynthesis, and function, particularly sialylation and its role in cellular communication and immune responses.
• Synthetic Biology: It is applied in synthetic biology to generate modified sialylated glycans for therapeutic, diagnostic, or research purposes.

Potential Impact:

• Therapeutic Development: The bioorthogonal properties of CMP-Neu5Az make it a valuable tool in developing therapies targeting sialylated structures, such as cancer cell glycans or viral glycoproteins.
• Glycosylation Studies: CMP-Neu5Az is a key tool in understanding the role of sialylation in health and disease, particularly in cancer metastasis, immune evasion, and microbial pathogenesis.

Key Research Areas:

• Cancer Biology: Sialylation plays a significant role in cancer biology, making CMP-Neu5Az useful for exploring cancer cell surface glycan alterations.
• Immunology: CMP-Neu5Az is used to investigate the role of sialylated glycans in immune modulation and pathogen-host interactions.

Conclusion:

CMP-Neu5Az is an essential tool in glycosylation research, enabling the specific labeling and tracking of sialylated glycans in biological systems. Its application in bioorthogonal chemistry makes it invaluable for studying sialic acid biology, with potential implications in therapeutic development, synthetic biology, and glycobiology research.