202343-12-2

Basic information

• Product Name: (2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
• CAS NO: 202343-12-2
• Molecular Weight: 334.286
• Mol File: 202343-12-2.mol

Chemical Properties

• CAS DataBase Reference: (2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (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)
• EPA Substance Registry System: (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)

Safety Data

• Hazardous Substances Data: 202343-12-2(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
(2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid is used as a pharmaceutical candidate for the development of new drugs due to its unique structure and functional groups, which may exhibit specific biological activities and interactions with biological targets.
Used in Biochemistry:
In biochemistry, (2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid may be utilized as a research tool to study enzyme mechanisms, protein interactions, or other biochemical processes, given its complex structure and functional groups.
Used in Organic Synthesis:
(2R,4S,5R,6R)-5-Acetylamino-2-azido-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid is used as a synthetic intermediate or building block in the synthesis of more complex organic compounds, taking advantage of its reactivity and structural features to create novel molecules with potential applications in various fields.

Upstream product

• 3063-71-6 cytidine-5'-monophosphono-N-acetylneuraminic acid 
• 189237-35-2 methyl [5-acetamido-3,5-dideoxy-2-azido-D-glycero-α-D-galacto-non-2-ulopyranoside]onate 

Relevant articles and documents

Synthesis and biological evaluation of non-hydrolyzable 1,2,3-triazole-linked sialic acid derivatives as neuraminidase inhibitors

αa-Sialic acid, azide 1 has been used as a substrate for the efficient preparation of 1,2,3-triazole derivatives of sialic acid using the copper-catalyzed azide-alkyne Huisgen cycloaddition ("click chemistry"). Our approach is to generate nonnatural N-glycosides of sialic acid, that are resistant to neuraminidase-catalyzed hydrolysis as opposed, to the natural Oglycosides. These N-glycosides would act as neuraminidase inhibitors to prevent the release of new virions. As a preliminary study, a small library of 1,2,3-triazole-linked sialic acid, derivatives has been synthesized in 71-89% yield. A. disaccharide mimic of sialic acid, has also been prepared using the α-sialic acid azide 1 and a C-8 propargyl sialic acid acceptor in 68 % yield. A model sialic acid coated dendrimer was also synthesized from a perpropargylated pentaerythritol acceptor. These novel sialic acid derivatives were then evaluated, as potential neuraminidase inhibitors using a 96-well plate fluorescence assay; micromolar IC50 values were observed, comparable to the known sialidase inhibitor Neu5Ac2en.

The N-acetyl neuraminyl oxecarbenium ion is an intermediate in the presence of anionic nucleophiles

Solvolysis of CMP N-acetyl neuraminate (CMP-NeuAc) in 1.8 M acetate buffer at pH 5 containing 0.9 M azide results in the formation of both anomers of 2-deoxy-2-azido N-acetyl neuraminic acid in addition to N-acetyl neuraminic acid as determined by 1H-NMR product analysis. A rate dependence on [azide] was observed with an apparent bimolecular rate constant of (2.1 ± 0.30) x 10-3 M-1 min-1 which could only account for half of the azido- NeuAc formed. Comparison of rate, product ratio, and stereochemical data indicate that concurrent pathways for formation of N3-NeuAc are operative, with 17% of product forming from reaction of azide and the tight ion pair. 12% via the solvent separated ion pair, and 6% from the free NeuAc oxocarbenium ion. From the corrected product ratio data, the lifetime of the oxocarbenium ion was estimated to be ≤ 3 x 10-11 s. Solvolysis of CMP- NeuAc at pL. = 5.0 afforded an observed solvent deuterium isotope effect (SDIE) k(H2O)/k(D2O) = 0.45, consistent with specific acid catalysis of glycosidic bond cleavage. A SDIE of 0.66 for the apparent bimolecular azide trapping pathway was also observed. An apparent isotope effect of ~1.1 for trapping of the N-acetyl neuraminyl oxocarbenium ion by water was determined by product analysis of azide trapping in H2O and D2O. An ab initio transition state for attack of water on an N-acetyl neuraminyl oxocarbenium ion model was located which featured a hydrogen bond between the oxocarbenium ion carboxylate and water; proton transfer was not part of the reaction coordinate. It is proposed that the N-acetyl neuraminate carboxylate group stabilizes an intermediate oxocarbenium ion, but the barrier for capture by water is lowered by a transition state hydrogen bond.