Synonyms:Mulkine
98.0%, *data from raw suppliers
Neu5Ac *data from reagent suppliers
Xi
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:
Reference yield: 85.0%
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The research focuses on the Perfluoroaryl Azide-Staudinger Reaction, a fast and bioorthogonal chemical reaction between perfluoroaryl azides (PFAAs) and aryl phosphines. The study reports a high reaction rate constant of 18 M-1 s-1 under ambient conditions, leading to the formation of stable iminophosphorane products that are resistant to hydrolysis and aza-Wittig reactions. The experiments involved mixing PFAA 1a and phosphine 2a in acetonitrile, observing the immediate color change and subsequent release of nitrogen gas, and confirming the product structure through single crystal X-ray crystallography. Kinetic analyses were performed to determine the reaction order and rate constants, with solvent effects and substituent effects on the PFAA core and phosphine structures being investigated. The bioorthogonality of the reaction was tested using the N-acetylneuraminic acid metabolic pathway, with PFAA-derivatized sugars being taken up by A549 cells and successfully labeled with phosphine-derivatized fluorescent bovine serum albumin. The experiments utilized techniques such as 1H NMR for monitoring reaction progress, flow cytometry for analyzing cell labeling, and fluorescence microscopy for visualizing labeled cells.
The research focuses on the synthesis of fluorescent 4-methyl-7-thiocoumaryl S-glycosides of sialic acid, which serve as fluorogenic substrates for tracing and quantifying sialidase activity in biological systems. The purpose of this study is to develop new tools for investigating the biological functions of sialic acid in glycoconjugates on bacterial and viral outer membranes. The researchers successfully synthesized three new fluorogenic substrates: 4-methylcoumarin-7-yl S-glycosides of N-acetylneuraminic acid, N-glycolylneuraminic acid, and 3-deoxy-D-glucose-D-galacto-2-nonulopyranosonic acid (KDN). They also developed a method for the preparation of a key intermediate, benzyl 5-amino-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosidonic acid (7), which is crucial for the synthesis of N-glycolylneuraminic acid. The synthesis involved various chemicals, including 4-methyl-7-thiocoumarin sodium salt, methyl 5-N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-D-glycero-D-galacto-2-nonulopyranosonate, and other related compounds, with the process utilizing Williamson reaction conditions and deprotection steps to yield the final products. The structures of the synthesized materials were confirmed using proton nuclear magnetic resonance (1H-NMR) and carbon-13 nuclear magnetic resonance (13C-NMR) spectroscopy.
The research details a novel synthesis of N-acetylneuraminic acid (Neu5Ac) and its deuterated analog [6-2H]-Neu5Ac from N-acetyl-D-glucosamine. The purpose of this study was to develop a straightforward and general method for synthesizing these compounds, which are crucial components of many glycoconjugates and are essential for studying the relationship between the structure of sialic acid residues and the function of glycoconjugates, as well as the mode of action of enzymes involved in their biosynthesis and transformation. The synthesis involves several key steps, including the Henry reaction of a 1-deoxy-1-nitro derivative of N-acetyl-D-glucosamine (protected 1-C-nitroanhydro-D-glucitol) with cyclohexylidene-α-glyceraldehyde, followed by acetylation, reductive denitration with Bu3SnH, debenzylation, catalytic oxidation, hydrolysis, esterification, and final acetylation. The study concludes that this method provides a convenient route for synthesizing Neu5Ac and its derivatives, allowing for modifications at various positions (C-1 to C-9) of the molecule, which can be useful for further studies and applications in glycobiology.
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