CMP-Neu5Gc, Cytidine-5-monophospho-N-glycolylneuraminic acid disodium salt
CMP-Neu5Gc.2Na (Cytidine Monophosphate N-glycolylneuraminic acid disodium salt) is a nucleotide sugar involved in the biosynthesis of sialic acids, specifically N-glycolylneuraminic acid (Neu5Gc). Neu5Gc is a sialic acid derivative commonly found in non-human mammals and plays critical roles in various biological processes, including cell-cell interactions, immune response, and pathogen recognition.
Structure & Properties:
- Molecular Weight (MW): Approximately 638 g/mol (depending on specific form and substitutions)
- Chemical Formula: C20H32N3Na2O17P2 (approximate)
- Synonyms: CMP-N-glycolylneuraminic acid disodium salt, Cytidine monophosphate N-glycolylneuraminic acid
- Functional Groups: Contains a glycolyl group (-CH2OH) attached to the amino group at the 5-position of the sialic acid backbone, distinguishing Neu5Gc from Neu5Ac (N-acetylneuraminic acid).
Biological Role:
- Biosynthesis Pathway: CMP-Neu5Gc is synthesized from CMP-Neu5Ac through a hydroxylation reaction catalyzed by the enzyme CMP-Neu5Ac hydroxylase, which adds a glycolyl group to the amino group of Neu5Ac, converting it into Neu5Gc.
- Function: It serves as a sugar donor in the glycosylation of glycoconjugates, such as glycoproteins and glycolipids, where Neu5Gc residues are incorporated into terminal positions of oligosaccharides.
Applications:
- Sialic Acid Research: CMP-Neu5Gc is essential for studying sialic acid biology, particularly in understanding the differences between Neu5Ac and Neu5Gc in glycosylation and their functional implications.
- Pathogen Interaction Studies: Neu5Gc is recognized by various pathogens and immune cells, making it a key molecule in studying host-pathogen interactions, immune response, and xenotransplantation.
Research Significance:
- Comparative Glycobiology: Neu5Gc is absent in humans due to a gene mutation, making its study important for understanding the immunological differences between humans and other mammals. Neu5Gc incorporation into human tissues via diet (e.g., red meat) has been linked to inflammation and certain diseases.
- Cancer Research: CMP-Neu5Gc is used in cancer research to explore the accumulation of Neu5Gc in human tumors, which may contribute to tumor progression and immune system evasion.
Storage and Stability:
- Storage: CMP-Neu5Gc should be stored at -20°C in a moisture-free environment to maintain stability.
- Stability: The compound is stable under these storage conditions but may degrade when exposed to heat, moisture, or light.
Research Applications:
- Immunology: CMP-Neu5Gc is employed in studies investigating the human immune response to Neu5Gc, particularly in the context of xenoantigenicity (immune reactions to non-human sugars).
- Glycosylation Pathways: Researchers use CMP-Neu5Gc to study glycosylation processes in non-human mammalian cells and tissues, as well as in synthetic biology applications.
Key Research Areas:
- Xenoantigenicity and Diet: Research focuses on how Neu5Gc from dietary sources (like red meat) is incorporated into human tissues and the resulting immune reactions, which may contribute to chronic inflammation and diseases such as cancer.
- Sialic Acid Diversity: CMP-Neu5Gc is important in studying the diversity of sialic acids across species, contributing to insights into evolutionary biology and pathogen specificity.
Conclusion:
CMP-Neu5Gc.2Na plays a significant role in sialic acid biology, particularly in the study of Neu5Gc’s function in glycosylation processes and immune interactions. Its importance extends to research on diet-induced inflammation, cancer, and xenoantigenicity, making it a valuable tool in glycobiology and biomedical research
