N-Acetyl-alpha-neuraminic acid

Base Information

• Chemical Name: N-Acetyl-alpha-neuraminic acid
• CAS No.: 21646-00-4
• Molecular Formula: C₁₁H₁₉NO₉
• Molecular Weight: 309.273
• 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: 21646-00-4.mol

Synonyms:Mulkine

Chemical Property of N-Acetyl-alpha-neuraminic acid

Chemical Property:

• Boiling Point: 805°Cat760mmHg
• PKA: 2.31±0.70(Predicted)
• Flash Point: 440.7°C
• PSA: 176.78000
• Density: 1.64g/cm³
• LogP: -3.48090
• 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:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

Technology Process of N-Acetyl-alpha-neuraminic acid

There total 19 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:

N-[(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate]-3',4'-dimethylpyridinium (300595-03-3) → 3,4-Lutidin (583-58-4) + N-acetyl neuraminic acid (6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,489-46-3,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9)

Guidance literature:

With influenza viral α-sialidase (A/Tokyo/3/67); at 37 ℃; pH=6.0; Further Variations:; pH-values; Enzyme kinetics;

DOI:10.1021/ja001641x

Reference yield:

(2S,4S,5R,6R)-5-Acetylamino-4-hydroxy-2-(3-nitro-phenoxy)-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid → sialic acid (489-46-3,6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) + meta-nitrophenol (554-84-7)

Guidance literature:

With sodium perchlorate; water; at 50 ℃; Rate constant; ionic strength 0.300 M; var. pH and temp.;

DOI:10.1021/ja00052a011

Reference yield:

cytidine-5'-monophosphono-N-acetylneuraminic acid (3063-71-6) → N-acetyl neuraminic acid (6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,489-46-3,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) + sialic acid (489-46-3,6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) + cytidine monophosphate (63-37-6,30811-80-4) + (2S,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid (202343-12-2) + (2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid (202343-12-2)

Guidance literature:

With sodium azide; acetate buffer; at 37 ℃; Rate constant; Product distribution; Mechanism; also in D₂O and in absence of azide; also in the presence of MeOH; solvent deuterium kinetic isotope effect;

DOI:10.1021/ja972503j

upstream raw materials:

cytidine-5'-monophosphono-N-acetylneuraminic acid

N-[(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate]pyridinium

N-[(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate]-3'-methylpyridinium

N-[(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate]-4'-methylpyridinium

Downstream raw materials:

N-acetylneuraminic acid methyl ester

N-Acetyl-β-D-neuraminylsaeure-methyl-methylglycosid

N-acetylneuraminic acid methyl ester

N-acetyl-D-mannosamine

Refernces

• 1、 Reyes Martinez, Juana Elizabeth,Sardzik, Robert,Voglmeir, Josef,Flitsch, Sabine L.. "Enzymatic synthesis of colorimetric substrates to determine α-2,3- and α-2,6-specific neuraminidase activity". . p. 21335 - 21338. Retrieved 2013/11/06.
• 2、 Blume, Astrid,Neubacher, Bjoern,Thiem, Joachim,Peters, Thomas. "Donor substrate binding to trans-sialidase of Trypanosoma cruzi as studied by STD NMR". . p. 1904 - 1909. Retrieved 2008/03/11.