24967-27-9

Basic information

• Product Name: N-ACETYLNEURAMINIC ACID, 2,3-DEHYDRO-2-DEOXY-, SODIUM SALT
• Synonyms: 2-deoxy-2,3-dehydro-n-acetylneuraminicacid;N-ACETYLNEURAMINIC ACID, 2,3-DEHYDRO-2-DEOXY-, SODIUM SALT;N-ACETYL-2,3-DEHYDRO-2-DEOXYNEURAMINIC ACID;N-ACETYL-2,3-DEHYDRO-2-DEOXYNEURAMINIC ACID SODIUM SALT;1,3-DEHYDRO-2-DEOXY-N-ACETYLNEURAMINIC ACID;2,3-DEHYDRO-2-DEOXY-N-ACETYLNEURAMINIC ACID;N-acetyl-2,3-didehydro-2-deoxyneuraminic acid;N-ACETYL-2 3-DEHYDRO-2-DEOXYNEURAMINIC &
• CAS NO: 24967-27-9
• Molecular Formula: C₁₁H₁₇NO₈
• Molecular Weight: 291.25
• EINECS: 246-550-7
• Product Categories: Pharm intermediate
• Mol File: 24967-27-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 227-228
• Boiling Point: 773.4ºC at 760 mmHg
• Flash Point: 421.6ºC
• Appearance: /
• Density: 1.58g/cm3
• Vapor Pressure: 1.27E-27mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: −20°C
• Solubility: H2O: soluble50mg/mL, clear, colorless
• PKA: 3.90±0.70(Predicted)
• BRN: 8722455
• CAS DataBase Reference: N-ACETYLNEURAMINIC ACID, 2,3-DEHYDRO-2-DEOXY-, SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYLNEURAMINIC ACID, 2,3-DEHYDRO-2-DEOXY-, SODIUM SALT(24967-27-9)
• EPA Substance Registry System: N-ACETYLNEURAMINIC ACID, 2,3-DEHYDRO-2-DEOXY-, SODIUM SALT(24967-27-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 24967-27-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 24967-27-9 differently. You can refer to the following data:
1. Neuraminidase (sialidase) inhibitor
2. N-Acetylneuraminic Acid, 2,3-Dehydro-2-deoxy-, Sodium Salt is a bacterial, viral, and mammalian neuraminidase inhibitor. It can be used in biological study of knockdown of Neu4 and injection of sialidase inhibitor such as DANA resulted in impairment of long-term potentiation at mossy fiber-CA3 synapses and hippocampus-dependent spatial memory in rats.

Definition

ChEBI: N-Acetylneuraminic acid reduced across the 2,3-bond with loss of the hydroxy group at C-2; it is a minor component of body fluids although abundant in sialuria.

InChI:InChI=1/C11H17NO8/c1-4(14)12-8-5(15)2-7(11(18)19)20-10(8)9(17)6(16)3-13/h2,5-6,8-10,13,15-17H,3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,8+,9+,10+/m0/s1

Upstream product

• 72-87-7 N-acetyl-D-mannosamine 
• 18409-13-7 3'-sialyllactose 
• 64-17-5 ethanol 
• 26112-88-9 2-O-(p-nitrophenyl)-5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranusonic acid 
• 28079-86-9 4-nitrophenyl (5-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonic acid) 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 25875-99-4 methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate 
• 3063-71-6 cytidine-5'-monophosphono-N-acetylneuraminic acid 
• 909103-75-9 methyl 5-acetamido-2,6-anhydro-4-O-(2-thiocarbamoylethyl)-3,5-dideoxy-7,8,9-tri-O-acetyl-D-glycero-D-galacto-non-2-enonate 
• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 

Downstream Products

• 6730-42-3 Neu5AcαOMe 
• 39937-91-2 2,6-anhydro-3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-D-galacto-non-2-enoic acid 
• 22900-11-4 (2R,3R,4S)-3-acetamido-4-hydroxy-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid 
• 116096-68-5 O--(2->6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose 
• 116096-69-6 (2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 116096-67-4 methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-phenylseleno-D-erythro-α-L-gluco-nonulopyranosate 
• 116180-63-3 methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-(phenylseleno)-D-erythro-β-L-manno-2-nonulopyranosonate 
• 125288-70-2 methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylseleno-D-erythro-β-L-gluco-2-nonulopyranosonate 
• 125288-70-2 (3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-hydroxy-3-phenylselanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 116113-10-1 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 125288-74-6 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 116181-93-2 O--(2->6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose 
• 116096-64-1 (3R,4R,5S,6R)-2-Acetoxy-5-acetylamino-4-benzyloxy-3-phenylselanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 116096-63-0 methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 

Relevant articles and documents

A glycal-based photoaffinity probe that enriches sialic acid binding proteins

To identify sialic acid binding proteins from complex proteomes, three photocrosslinking affinity-based probes were constructed using Neu5Ac (5 and 6) and Neu5Ac2en (7) scaffolds. Kinetic inhibition assays and Western blotting revealed the Neu5Ac2en-based 7 to be an effective probe for the labeling of a purified gut microbial sialidase (BDI_2946) and a purified human sialic acid binding protein (hCD33). Additionally, LC–MS/MS affinity-based protein profiling verified the ability of 7 to enrich a low-abundance sialic acid binding protein (complement factor H) from human serum thus validating the utility of this probe in a complex context.

Synthesis and chemical characterization of several perfluorinated sialic acid glycals and evaluation of their: In vitro antiviral activity against Newcastle disease virus

Newcastle Disease Virus (NDV), belonging to the Paramyxoviridae family, causes a serious infectious disease in birds, resulting in severe losses in the poultry industry every year. Haemagglutinin neuraminidase glycoprotein (HN) has been recognized as a key protein in the viral infection mechanism, and its inhibition represents an attractive target for the development of new drugs based on sialic acid glycals, with the 2-deoxy-2,3-didehydro-d-N-acetylneuraminic acid (Neu5Ac2en) as their backbone. Herein we report the synthesis of several Neu5Ac2en glycals and of their perfluorinated C-5 modified derivatives, including their respective stereoisomers at C-4, together with evaluation of their in vitro antiviral activity. While all synthesized compounds were found to be active HN inhibitors in the micromolar range, we found that their potency was influenced by the chain-length of the C-5 perfluorinated acetamido functionality. Thus, the binding modes of the inhibitors were also investigated by performing a docking study. Moreover, the perfluorinated glycals were found to be more active than the corresponding normal C-5 acylic derivatives. Finally, cell-cell fusion assays on NDV infected cells revealed that the addition of a newly synthesized C-4α heptafluorobutyryl derivative almost completely inhibited NDV-induced syncytium formation.

INHIBITORS OF SIALIDASE OR SIALIDASE-LIKE ENZYMES

The present invention describes compounds of Formula I or a pharmaceutically acceptable salts or derivatives thereof. Compositions comprising compounds of Formula I are also described. The present invention further relates to a method of producing non-2-enonate compounds.