N-Acetylneuraminicacid2, 4, 7, 8, 9-pentaacetate, CAS:4887-11-0

2,4,7,8,9-Penta-O-acetyl N-acetylneuraminic acid (commonly known as Neu5Ac5 or PANA) is an important sialic acid molecule found in a variety of glycoconjugates present in biological systems. It is a nine-carbon acidic sugar that is added to the end of a range of cell surface molecules, called glycans. Glycans are involved in many biological processes, including cell-to-cell communication, cell adhesion, and immune recognition. Sialic acids like Neu5Ac play a critical role in many of these processes. Synthesis and Characterization: Neu5Ac is synthesized in a variety of ways, including enzymatic and chemical methods. For example, one common method involves the enzymatic synthesis of Neu5Ac from N-acetylmannosamine (ManNAc) using the enzyme CMP-Neu5Ac synthetase. This reaction produces CMP-Neu5Ac (CMP = cytidine monophosphate), which can then be converted to Neu5Ac by the enzyme CMP-Neu5Ac hydrolase. Analytical Methods: There are several analytical methods developed for the detection, quantification, and characterization of Neu5Ac. Chromatography-based techniques such as HPLC (High-Performance Liquid Chromatography), TLC (Thin-Layer Chromatography), and GC-MS (Gas Chromatography-Mass Spectrometry) are commonly used to analyze Neu5Ac. Other methods include electrophoresis, NMR (Nuclear Magnetic Resonance) spectroscopy, and FT-IR (Fourier-Transform Infrared) spectroscopy. Biological Properties: As mentioned earlier, Neu5Ac is involved in many biological processes, including cell adhesion, immune recognition, and pathogen-host interactions. Studies have shown that sialic acids like Neu5Ac can modulate immune responses, alter cell surface receptor function, and affect the pathogenicity of certain viruses and bacteria. Toxicity and Safety in Scientific Experiments: Studies have assessed the potential toxicity and safety of Neu5Ac in scientific experiments. Neu5Ac has been found to be safe and non-toxic in animal studies when administered orally or via injection. However, more research is needed to confirm its safety in human subjects. Applications in Scientific Experiments: Neu5Ac has several applications in scientific experiments, including its use as a substrate for sialyltransferases (enzymes that transfer sialic acids to glycan structures) and in the synthesis of sialylated compounds. It also serves as a starting material for the synthesis of CMP-Neu5Ac, which is used in the enzymatic synthesis of sialylated glycans. Current State of Research: Research on Neu5Ac is ongoing, with several studies investigating its role in various biological processes and its potential therapeutic applications. Recent studies have shown that Neu5Ac can modulate innate immune responses and improve the efficacy of cancer immunotherapy. Potential Implications in Various Fields of Research and Industry: Neu5Ac has potential implications in various fields of research and industry, including immunology, glycoscience, and biotechnology. Its ability to modulate immune responses and its involvement in cell adhesion and receptor function make it an important target for drug development. Limitations and Future Directions: Despite the significant advances made in the understanding of Neu5Ac, there are still limitations and future directions that need to be addressed. For example, more research is needed to elucidate the mechanisms by which Neu5Ac modulates immune responses and its role in cancer immunotherapy. Additionally, the development of more efficient methods for the synthesis of sialylated compounds and CMP-Neu5Ac is needed to facilitate further research in this area. Future Directions: - Development of novel sialyltransferases with improved efficiency and specificity - Investigation of the role of Neu5Ac in other disease states, such as autoimmune disorders and neurodegenerative diseases - Synthesis of sialylated compounds with potential therapeutic applications - Development of new methodologies for the detection and quantification of Neu5Ac in biological samples - Study of the effects of Neu5Ac on the gut microbiome - Exploration of Neu5Ac as a potential therapeutic target in the treatment of viral infections - Investigation of the effects of Neu5Ac on neuronal signaling and cognitive function - Development of more efficient methods for the synthesis of CMP-Neu5Ac and sialylated glycans - Exploration of the role of Neu5Ac in the development and progression of cancer - Investigation of the effects of Neu5Ac on the host immune system in the context of infectious diseases. CAS Number 4887-11-0 Product Name 2,4,7,8,9-Penta-O-acetyl N-acetylneuraminic acid IUPAC Name (2R,4S,5R,6R)-5-acetamido-2,4-diacetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid Molecular Formula C21H29NO14 Molecular Weight 519.45 g/mol InChI InChI=1S/C21H29NO14/c1-9(23)22-17-15(32-11(3)25)7-21(20(29)30,35-14(6)28)36-19(17)18(34-13(5)27)16(33-12(4)26)8-31-10(2)24/h15-19H,7-8H2,1-6H3,(H,22,23)(H,29,30)/t15-,16+,17+,18+,19+,21-/m0/s1 InChI Key MYVACZVKCHHJHJ-JSNLTNBWSA-N SMILES CC(=O)NC1C(CC(OC1C(C(COC(=O)C)OC(=O)C)OC(=O)C)(C(=O)O)OC(=O)C)OC(=O)C Canonical SMILES CC(=O)NC1C(CC(OC1C(C(COC(=O)C)OC(=O)C)OC(=O)C)(C(=O)O)OC(=O)C)OC(=O)C Isomeric SMILES CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](COC(=O)C)OC(=O)C)OC(=O)C)(C(=O)O)OC(=O)C)OC(=O)C CAS No: 4887-11-0 Synonyms: N-Acetylneuraminic acid 2,4,7,8,9-pentaacetate MDL No: MFCD18643103 Chemical Formula: C21H29NO14 Molecular Weight: 519.45