N-Acetyl-alpha-neuraminic acid

Base Information

• Chemical Name: N-Acetyl-alpha-neuraminic acid
• CAS No.: 131-48-6
• Molecular Formula: C11H19NO9
• Molecular Weight: 309.273
• Hs Code.: 29329970
• European Community (EC) Number: 205-023-1
• UNII: 04A90EXP8V
• DSSTox Substance ID: DTXSID201309514
• Nikkaji Number: J614.853K
• Wikipedia: N-Acetylneuraminic_acid
• Wikidata: Q310828
• Metabolomics Workbench ID: 37419
• ChEMBL ID: CHEMBL1234621
• Mol file: 131-48-6.mol

Synonyms:Mulkine

Chemical Property of N-Acetyl-alpha-neuraminic acid

Chemical Property:

• Appearance/Colour: Crystalline
• Vapor Pressure: 5.5E-30mmHg at 25°C
• Melting Point: 184-186 °C
• Refractive Index: -32 ° (C=1, H2O)
• Boiling Point: 395.6 °C at 760 mmHg
• PKA: 2.41±0.54(Predicted)
• Flash Point: 193 °C
• PSA: 176.78000
• Density: 1.727 g/cm³
• LogP: -3.48090
• Storage Temp.: −20°C
• Sensitive.: Air Sensitive
• Solubility.: 50 g/L (20°C)
• Water Solubility.: 50 g/L (20 ºC)
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 309.10598118
• Heavy Atom Count: 21
• Complexity: 403

Purity/Quality:

98% up ^*data from raw suppliers

Neu5Ac ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• Canonical SMILES: CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H](C[C@@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O)O
• Recent EU Clinical Trials: A Phase 2 Open-label study to Evaluate the Safety of Aceneuramic Acid Extended
• Description: N-acetylneuraminic acid is an N-acyl derivative of neuraminic or acid amino sugar derivative, derived from N-acetylmannosamine and pyruvic acid. It is an important constituent of glycoproteins and glycolipids. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria.
• Physical properties: The numbering of the sialic acid structure begins at the carboxylate carbon and continues around the chain. The configuration which places the carboxylate in the axial position is the alpha-anomer. The alpha-anomer is the form that is found when sialic acid is bound to glycans, however, in solution it is mainly (over 90 %) in the beta-anomeric form. A bacterial enzyme with sialic acid mutarotase activity, NanM, has been discovered which is able to rapidly equilibrate solutions of sialic acid to the resting equilibrium position of around 90 % beta 10 % alpha.
• Uses: N-Acetylneuraminic acid is an integral part of sialic acids (SAs), important functional sugars that play an important role in maintaining and improving brain health, detoxification, antibacterial, and immune enhancement. n-Acetylneuraminic acid is biologically useful for neurotransmission, leukocyte extravasation, viral or bacterial infection, and carbohydrate-protein recognition. n- Acetylneuraminic acid is used to study its biochemistry, metabolism and absorption in vivo and in vitro.
• Biological Functions: Sialic acid-rich glycoproteins (sialoglycoproteins) bind selectin in humans and other organisms. Metastatic cancer cells often express a high density of sialic acid-rich glycoproteins. This overexpression of sialic acid on surfaces creates a negative charge on cell membranes. This creates repulsion between cells (cell opposition) and helps these late-stage cancer cells enter the blood stream. Sialic acid also plays an important role in human influenza infections. Many bacteria also use sialic acid in their biology, although this is usually limited to bacteria that live in association with higher animals (deuterostomes). Many of these incorporate sialic acid into cell surface features like their lipopolysaccharide and capsule, which helps them evade the innate immune response of the host.[6] Other bacteria simply use sialic acid as a good nutrient source, as it contains both carbon and nitrogen and can be converted to fructose-6- phosphate, which can then enter central metabolism. Sialic acid-rich oligo saccharides on the glyco conjugates ( glyco lipids, glyco proteins, proteoglycans) found on surface membranes help keep water at the surface of cells . The sialic acid - rich regions contribute to creating a negative charge on the cells' surfaces. Since water is a polar molecule with partial positive charges on both hydrogen atoms, it is attracted to cell surfaces and membranes. This also contributes to cellular fluid uptake. Sialic acid can "hide" mannose antigens on the surface of host cells or bacteria from mannose - binding lectin . This prevents activation of complement. Sialic acid in the form of poly sialic acid is an unusual posttranslational modification that occurs on the neural cell adhesion molecules (NCAMs). In the synapse, the strong negative charge of the polysialic acid prevents NCAM cross-linking of cells.

Technology Process of N-Acetyl-alpha-neuraminic acid

There total 11 articles about N-Acetyl-alpha-neuraminic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

→ N-Acetylneuraminic acid (131-48-6,14752-56-8,5977-25-3,6225-16-7,6918-20-3)

Guidance literature:

Reference yield:

5-(1-acetylamino-2,3,4,5-tetrahydroxy-pentyl)-2-tert-butyl-isoxazolidine-3-carboxylic acid ethyl ester → N-Acetylneuraminic acid (131-48-6,14752-56-8,5977-25-3,6225-16-7,6918-20-3)

Guidance literature:

5-(1-acetylamino-2,3,4,5-tetrahydroxy-pentyl)-2-tert-butyl-isoxazolidine-3-carboxylic acid ethyl ester; With sodium methylate; In methanol; at 20 ℃;

With water; for 24h;

DOI:10.1002/anie.200601555

Reference yield:

5-amino-hept-6-ene-1,2,3,4-tetraol → N-Acetylneuraminic acid (131-48-6,14752-56-8,5977-25-3,6225-16-7,6918-20-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydrogen carbonate / methanol / 1 h

2.1: dioxane / 336 h / 30 °C

3.1: NaOMe / methanol / 20 °C

3.2: water / 24 h

With sodium methylate; sodium hydrogencarbonate; In 1,4-dioxane; methanol;

DOI:10.1002/anie.200601555

upstream raw materials:

Oxalacetic acid

2-acetamido-2-deoxy-D-glucose

D-glucose

piruvate

Downstream raw materials:

N-acetyl-neuraminic acid methyl ester

O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic-acid)-(2-3)-O-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-β-D-galactopyranose

O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic-acid)-(2-3)-O-β-D-galactopyranosyl-(1-3)-2-acetamido-2-deoxy-α-D-galactopyranose

N-acetyl-D-mannosamine

Refernces

• 1、 Xu, Ping,Qiu, Jian Hua,Zhang, Yi Nan,Chen, Jing,Wang, Peng George,Yan, Bing,Song, Jing,Xi, Ri Mo,Deng, Zi Xin,Ma, Cui Qing. "Efficient whole-cell biocatalytic synthesis of N-Acetyl-D-neuraminic acid". . p. 1614 - 1618. Retrieved 2007.
• 2、 Hamamoto, Tomoki,Takeda, So,Noguchi, Toshitada. "Enzymatic synthesis of cytidine 5′-monophospho-N-acetylneuraminic acid". . p. 1944 - 1950. Retrieved 2005.
• 3、 Hong, Zhangyong,Liu, Lei,Hsu, Che-Chang,Wong, Chi-Huey. "Three-step synthesis of sialic acids and derivatives". . p. 7417 - 7421. Retrieved 2007/10/03.