4887-11-0

Basic information

• Product Name: N-Acetylneuraminicacid2,4,7,8,9-pentaacetate
• Synonyms: N-Acetylneuraminicacid2,4,7,8,9-pentaacetate;2,4,7,8,9-Penta-O-acetyl N-acetylneuraminic acid;Zanamivir intermediate Ds;(2R,4S,5R,6R)-5-acetamido-2,4-diacetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylic acid
• CAS NO: 4887-11-0
• Molecular Formula: C21H29NO14
• Molecular Weight: 519.46
• Mol File: 4887-11-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: N-Acetylneuraminicacid2,4,7,8,9-pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetylneuraminicacid2,4,7,8,9-pentaacetate(4887-11-0)
• EPA Substance Registry System: N-Acetylneuraminicacid2,4,7,8,9-pentaacetate(4887-11-0)

Safety Data

• Hazardous Substances Data: 4887-11-0(Hazardous Substances Data)

Usage

Description

N-Acetylneuraminicacid2,4,7,8,9-pentaacetate is a derivative of neuraminic acid, a crucial component of various biological molecules such as glycoproteins and glycolipids. N-Acetylneuraminicacid2,4,7,8,9-pentaacetate is characterized by the presence of five acetate groups attached to its structure, which play a significant role in its functionality and applications.

Uses

Used in Pharmaceutical Industry:
N-Acetylneuraminicacid2,4,7,8,9-pentaacetate is used as a therapeutic agent for the treatment of sialic acid-deficient myopathy, a rare genetic disorder characterized by progressive muscle weakness and atrophy. As a derivative of neuraminic acid, it efficiently rescues the muscle phenotype and biochemical defects in mouse models of the disease, offering potential therapeutic benefits for patients suffering from this condition.
Used in Research and Development:
In addition to its pharmaceutical applications, N-Acetylneuraminicacid2,4,7,8,9-pentaacetate is also utilized in research and development for the study of sialic acid-related biological processes and the development of novel therapeutic strategies targeting sialic acid metabolism. Its unique structure and properties make it a valuable tool for investigating the role of sialic acid in various cellular and molecular pathways.

Upstream product

• 6813-81-6 N-acetyl neuraminic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 50669-91-5 (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid 
• 202194-39-6 (2R,4S,5R,6R)-5-Acetylamino-2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester 

Relevant articles and documents

Synthesis of sialic acid derivatives having a C{double bond, long}C double bond substituted at the C-5 position and their glycopolymers

Glycomonomers of sialic acid in which the acetamide group at C-5 was converted into two kinds of C{double bond, long}C double bond substituents were prepared and the fully protected glycomonomers were directly polymerized before deprotection steps. Radical polymerization with acrylamide in DMF in the presence of ammonium persulfate and N,N,N',N'-tetramethylethylenediamine proceeded smoothly and gave corresponding sialopolymers. Interestingly glycomonomers had hemagglutination inhibitory activities not only for H1N1 but also for H3N2 of human influenza virus strains.

Determination of the absolute configuration of sialic acids in gangliosides from the sea cucumber Cucumaria echinata

Enantiomeric pairs of sialic acid, D- and L-NeuAc (N-acetylneuraminic acid), were converted to D- and L-arabinose, respectively, by chemical degradation. Using this method, the absolute configuration of the sialic acid residues, NeuAc and NeuGc (N-glycolylneuraminic acid), in the gangliosides from the sea cucumber Cucumaria echinata was determined to be the D-form. Although naturally occurring sialic acids have been believed to be the D-form on the basis of biosynthetic evidence, this is the first report of the determination of the absolute configuration of the sialic acid residues in gangliosides using chemical methods.

Design and synthesis of a water-soluble taxol analogue: Taxol-sialyl conjugate

Glycosidation, using the methylthio derivative of N-acetylneuraminic acid 3, of linker alcohol 4 in DME with 'long-range participation' produced the α-glycosyl linkage with high stereoselectivity. The α-linked sialic acid 2 was introduced in taxol without protection of the alcohol functionality in sialic acid.