CMP-Neu5,9Ac2 ammonium salt - the key building block to unlock sialic acid glycosylation engineering

β-Neuraminic acid, N-acetyl-, 9-acetate 2-(hydrogen5'-cytidylate), ammonium salt (1:2) is a highly pure, biologically active sialic acid nucleoside monophosphate (CMP-sialic acid) derivative. It is not only a crucial glycosyl donor in enzymatic synthesis, but also an indispensable advanced intermediate in chemical-enzymatic synthesis, specifically used to introduce sialic acid with specific modifications at the end of the sugar chain. In the fields of glycobiology, drug development and diagnostic reagent research and development, it is an "enabling" molecule for constructing complex sugar structures and optimizing the efficacy of biopharmaceuticals.

Chemical Information

· Chemical name: β-Neuraminicacid, N-acetyl-, 9-acetate 2-(hydrogen 5'-cytidylate), ammonium salt (1:2)

· Common name/abbreviation: CMP-Neu5,9Ac₂ ammonium salt

· Chemical formula: C22H36N5O17P

· Molecular weight: 673.52g/mol

· CAS number: 1045785-97-4

Structural features

The structural essence of CMP-Neu5,9Ac₂ ammonium salt lies in its precise "activation" design:

· Activated glycosyl donor: Sialic acid (Neu5Ac) is linked to cytidine-5'-monophosphate (CMP) through its α-configuration glycosidic bond, forming a natural CMP-sialic acid analogue. This structure is the only substrate form recognized by sialyltransferases in all organisms, ensuring efficient biocatalysis.

· Specific 9-O-acetylation modification: Compared with ordinary CMP-Neu5Ac, it introduces an acetyl group on the 9th hydroxyl group of sialic acid. This modification is a key "switch" in regulating the biological function of sialic acid and can significantly change its interaction with receptors (such as selectins, sialic acid-binding immunoglobulin-like lectins Siglecs), thereby affecting cell recognition, adhesion and immune response.

· Stable ammonium salt form: Provided in the form of diammonium salt with high solubility, easy storage and use, ensuring its excellent stability and reaction efficiency in biochemical reaction systems.

Main applications and advantages

1. Development of new glycoconjugate drugs and vaccines

o Optimize therapeutic antibodies: Use sialyltransferase to introduce 9-O-acetylated sialic acid into the Fc segment or Fab segment sugar chain of therapeutic antibodies (such as monoclonal antibodies). This modification can regulate the immunogenicity, half-life and ADCC/CDC effect of the antibody, and is the core technology for the development of "biosimilars" and "biobetter" drugs.

o Designing tumor vaccines: The sialic acid modification pattern on tumor-associated antigens (e.g., glycopeptides, gangliosides) is an important marker for immune system recognition. Using CMP-Neu5,9Ac₂ as a substrate, these antigens can be precisely synthesized or reshaped for the development of therapeutic vaccines against cancer.

2. chemoenzymatic synthesis of complex oligosaccharides and sugar complexes

o Overcoming the bottleneck of chemical synthesis: The chemical synthesis of sialic acid is extremely challenging because of its multiple sites and difficult to control three-dimensional configuration. As an "activation module" for enzymatic synthesis, it is seamlessly connected with chemical synthesis. It can efficiently and highly stereoselectively introduce modified sialic acid into specific positions of oligosaccharide chains, glycolipids or glycoproteins, greatly simplifying the preparation process of complex sugar molecules.

o Construction of well-defined glycan libraries: Is an ideal tool to construct uniform oligosaccharide libraries containing specific sialic acid modifications (such as 9-O-Ac) for high-throughput screening to discover new drug targets or diagnostic markers.

3. Basic research and development of diagnostic tools

o Research on glycobiological mechanisms: 9-O-acetylated sialic acid plays a key role in cell signal transduction, pathogen infection (such as influenza virus, coronavirus), inflammatory response and immune regulation. This product is an essential probe molecule for studying its specific functions and mechanisms of action.

o Highly sensitive diagnostic reagents: Certain diseases (such as specific cancers, autoimmune diseases) can cause abnormal changes in the levels of 9-O-acetylated sialic acid in body fluids or cell surfaces. The detection methods or capture probes developed based on this product are expected to become a new generation of highly specific and sensitive in vitro diagnostic (IVD) tools.

Conclusion

Today, with the rapid development of precision medicine and glycoscience, precise manipulation of sugar chain structures has become the next frontier of drug innovation. CMP-Neu5,9Ac₂ ammonium salt is your passport to this frontier. From designing the next generation of smart antibodies, to deciphering the sugar code of disease, to developing innovative diagnostics, its potential is waiting for you to discover.