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84380-10-9 , N-Acetylneuraminic acid methyl ester 4,7,8,9-tetraacetate, CAS:84380-10-9

84380-10-9, N-Acetylneuraminic acid methyl ester 4,7,8,9-tetraacetate,
CAS:84380-10-9
C20H29NO13 / 491.44
MFCD08276266

4,7,8,9-Tetra-O-acetyl-N-acetyl-D-neuraminic acid methyl ester

N-乙酰神经氨酸甲酯-4,7,8,9-四乙酸酯,

4,7,8,9-Tetra-O-acetyl-N-acetyl-D-neuraminic acid methyl ester is a modified form of sialic acid. This compound is a glycosylation product that has been modified with methyl groups and fluorine atoms. The fluorination of the molecule increases its stability and prevents it from being hydrolyzed by enzymes such as β-galactosidase. 4,7,8,9-Tetra-O-acetyl-N-acetyl-D-neuraminic acid methyl ester is often used in the synthesis of polysaccharides and oligosaccharides for medical purposes. This compound can be custom synthesized for research purposes or to meet special requirements.

4,7,8,9-Tetra-O-acetyl-N-acetylneuraminic Acid Methyl Ester, also known as Neu5Ac4Ac, is a sialic acid derivative and an important biochemical compound. It is a synthetic disaccharide derivative of sialic acid, which is a common component of cell membranes and important for cell-to-cell communication.

Definition and Background

Sialic acids are a family of sugars that are found on the cell surface of many organisms, including humans. They play a crucial role in a wide range of cellular processes, including cellular recognition, signaling, and adhesion. Sialic acids are synthesized in the cell and are typically attached to glycoproteins and glycolipids in the cell membrane. Neu5Ac4Ac is a synthetic derivative of sialic acid and is used in many research applications.

Synthesis and Characterization

Neu5Ac4Ac can be synthesized from sialic acid through a series of chemical reactions. The most commonly used method involves the sialylation of a glucosamine derivative with a sialyl donor, followed by acetylation of the resulting disaccharide. The compound is then purified and characterized using a range of analytical techniques, including nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and high-performance liquid chromatography (HPLC).

Analytical Methods

Analytical methods such as NMR spectroscopy, MS, and HPLC are used to characterize Neu5Ac4Ac and to ensure its purity. The purity of the compound is important for research applications, as impurities can interfere with experimental results.

Biological Properties

Neu5Ac4Ac is involved in a wide range of biological processes, including cellular recognition and immune response. It is a key component of the influenza virus receptor and is also involved in the attachment of bacteria to host cells. Neu5Ac4Ac has been shown to inhibit the replication of some viruses, including the respiratory syncytial virus.

Toxicity and Safety in Scientific Experiments

The toxicity of Neu5Ac4Ac has not been extensively studied, but it is generally considered to be safe at low concentrations. However, caution should be taken when working with any chemical compound.

Applications in Scientific Experiments

Neu5Ac4Ac has a wide range of applications in scientific experiments. It is commonly used in glycoconjugate synthesis, where it is attached to a protein or lipid to create a glycoprotein or glycolipid. It is also used in the study of viruses, bacteria, and other pathogens, as well as in the study of cellular processes and immune responses.

Current State of Research

Neu5Ac4Ac continues to be an important area of research, with new applications and uses being explored. Researchers are investigating its potential use in vaccine development, as well as its role in immune evasion by pathogens. In addition, the synthesis of new sialic acid analogs is an active area of research.

Potential Implications in Various Fields of Research and Industry

Neu5Ac4Ac has potential implications in a wide range of fields, including vaccine development, the study of microbial pathogenesis, and the development of new therapeutics. It may also have applications in the food industry, where it could be used as an additive to improve the taste and nutritional value of certain foods.

Limitations and Future Directions

One limitation of Neu5Ac4Ac is its relatively high cost and the difficulty of synthesizing it in large quantities. Future research may focus on developing less expensive and more efficient methods of synthesis. Other areas of research may investigate the use of Neu5Ac4Ac in drug development, as well as its potential as a biomarker for disease diagnosis.

In summary, Neu5Ac4Ac is an important biochemical compound with a wide range of applications in scientific research. Its synthesis and characterization have been well-established, and its biological properties and potential implications in various fields of research and industry continue to be explored. Further research is needed to fully understand its potential benefits and limitations, and to develop new and more efficient methods of synthesis.

CAS Number84380-10-9
Product Name4,7,8,9-Tetra-O-acetyl-N-acetylneuraminic Acid Methyl Ester
IUPAC Namemethyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-hydroxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
Molecular FormulaC20H29NO13
Molecular Weight491.44 g/mol
InChIInChI=1S/C20H29NO13/c1-9(22)21-16-14(31-11(3)24)7-20(28,19(27)29-6)34-18(16)17(33-13(5)26)15(32-12(4)25)8-30-10(2)23/h14-18,28H,7-8H2,1-6H3,(H,21,22)/t14-,15+,16+,17+,18+,20-/m0/s1
InChI KeyCAKDMYCBPKFKCV-DCDDNHAVSA-N
SMILESCC(=O)NC1C(CC(OC1C(C(COC(=O)C)OC(=O)C)OC(=O)C)(C(=O)OC)O)OC(=O)C
Canonical SMILESCC(=O)NC1C(CC(OC1C(C(COC(=O)C)OC(=O)C)OC(=O)C)(C(=O)OC)O)OC(=O)C
Isomeric SMILESCC(=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)OC)O)OC(=O)C

CAS No: 84380-10-9 Synonyms: Methyl 5-Acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-b-D-glycero-D-galacto-2-nonulopyranosylonate 

 MDL No: MFCD08276266 Chemical Formula: C20H29NO13 Molecular Weight: 491.44


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