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

Description

N-Acetylneuraminic Acid, 2,3-Dehydro-2-deoxy-, Sodium Salt is a compound derived from the modification of N-Acetylneuraminic acid, where the hydroxy group at C-2 is removed, and the 2,3-bond is reduced. It is a minor component of body fluids but is abundant in sialuria. This sodium salt form of the compound has potential applications in various fields due to its neuraminidase inhibitory properties.

Uses

Used in Pharmaceutical Industry:
N-Acetylneuraminic Acid, 2,3-Dehydro-2-deoxy-, Sodium Salt is used as a neuraminidase (sialidase) inhibitor for the development of antiviral and antibacterial drugs. It targets neuraminidase enzymes, which are crucial for the replication and transmission of certain viruses and bacteria, thus helping in the treatment and prevention of infections.
Used in Biological Research:
In the field of biological research, N-Acetylneuraminic Acid, 2,3-Dehydro-2-deoxy-, Sodium Salt is used as a tool to study the effects of neuraminidase inhibition on various biological processes. For instance, it can be employed in the study of knockdown of Neu4 and the impact of sialidase inhibitor injection on long-term potentiation at mossy fiber-CA3 synapses and hippocampus-dependent spatial memory in rats. This helps researchers understand the role of neuraminidase in cognitive functions and neurological disorders.
Used in Diagnostic Applications:
N-Acetylneuraminic Acid, 2,3-Dehydro-2-deoxy-, Sodium Salt can also be utilized in the development of diagnostic tools and tests for detecting and monitoring the levels of neuraminidase enzymes in biological samples. This can aid in the early diagnosis and prognosis of diseases associated with abnormal neuraminidase activity.

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

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

Downstream Products

• 125288-69-9 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid 
• 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 
• 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 
• 116181-93-2 O--(2->6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose 
• 125288-74-6 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 116113-10-1 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 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 
• 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 
• 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 
• 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 
• 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 
• 116096-68-5 O--(2->6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose 
• 6730-42-3 Neu5AcαOMe 
• 39937-91-2 2,6-anhydro-3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-D-galacto-non-2-enoic acid 

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.