Cas no 23755-35-3 (2-O-Methyl-beta-D-N-acetylneuraminic Acid)

2-O-Methyl-beta-D-N-acetylneuraminic Acid is a modified sialic acid derivative widely used in glycobiology and medicinal chemistry research. Its key advantage lies in the methylation at the 2-O position, which enhances metabolic stability and resistance to enzymatic degradation compared to unmodified sialic acids. This modification makes it valuable for studying sialidase-resistant glycoconjugates, cell-surface interactions, and glycan-based therapeutics. The compound serves as a critical intermediate in synthesizing structurally defined oligosaccharides and glycoproteins. Its high purity and well-characterized structure ensure reproducibility in experimental applications, particularly in probing sialic acid-dependent biological processes such as cell signaling, pathogen recognition, and immune modulation.
2-O-Methyl-beta-D-N-acetylneuraminic Acid structure
23755-35-3 structure
Product Name:2-O-Methyl-beta-D-N-acetylneuraminic Acid
CAS No:23755-35-3
MF:C12H21NO9
MW:323.296444654465
CID:254119
PubChem ID:14160669
Update Time:2025-06-08

2-O-Methyl-beta-D-N-acetylneuraminic Acid Chemical and Physical Properties

Names and Identifiers

    • b-Neuraminicacid, N-acetyl-2-O-methyl- (9CI)
    • 2-O-METHYL-ALPHA-D-N-ACETYLNEURAMINIC ACID
    • 2-O-METHYL-B-D-N-ACETYLNEURAMINIC ACID
    • 2-O-Methyl-β-D-N-ace
    • 2-O-Methyl-β-D-N-acetylneuraminic Acid
    • 2-O-METHYL-α-D-N-ACETYLNEURAMINIC ACID
    • NJRVVFURCKKXOD-AGNBLMTLSA-N
    • 23755-35-3
    • 2-O-Methyl-beta-D-N-acetylneuraminic Acid
    • W-201998
    • (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
    • SCHEMBL7066109
    • methyl 5-acetamido-3,5-dideoxy-D-glycero-beta-D-galacto-2-nonulopyranosidonic acid
    • b-Neuraminicacid,N-acetyl-2-O-methyl-(9ci)
    • Inchi: 1S/C12H21NO9/c1-5(15)13-8-6(16)3-12(21-2,11(19)20)22-10(8)9(18)7(17)4-14/h6-10,14,16-18H,3-4H2,1-2H3,(H,13,15)(H,19,20)/t6-,7+,8+,9+,10+,12-/m0/s1
    • InChI Key: NJRVVFURCKKXOD-AGNBLMTLSA-N
    • SMILES: O1[C@](C(=O)O)(C[C@@H]([C@H]([C@@H]1[C@@H]([C@@H](CO)O)O)NC(C)=O)O)OC

Computed Properties

  • Exact Mass: 323.12200
  • Monoisotopic Mass: 323.12163125g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 6
  • Hydrogen Bond Acceptor Count: 9
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 6
  • Complexity: 417
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 6
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -2.9
  • Topological Polar Surface Area: 166?2

Experimental Properties

  • Melting Point: 162-165°C
  • Stability/Shelf Life: Moisture, Temperature sensitive
  • PSA: 165.78000
  • LogP: -2.82680

2-O-Methyl-beta-D-N-acetylneuraminic Acid Security Information

  • WGK Germany:3

2-O-Methyl-beta-D-N-acetylneuraminic Acid Pricemore >>

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Additional information on 2-O-Methyl-beta-D-N-acetylneuraminic Acid

Introduction to 2-O-Methyl-beta-D-N-acetylneuraminic Acid (CAS No. 23755-35-3)

2-O-Methyl-beta-D-N-acetylneuraminic Acid, with the chemical identifier CAS No. 23755-35-3, is a specialized glycoside derivative that has garnered significant attention in the field of medicinal chemistry and biochemistry. This compound is a modified form of sialic acid, a crucial component in numerous biological processes, and its unique structural properties make it a subject of extensive research and development. The introduction of a methyl group at the 2-O position and the presence of an N-acetyl moiety endow this molecule with distinct functionalities that are exploited in various therapeutic applications.

The significance of 2-O-Methyl-beta-D-N-acetylneuraminic Acid lies in its role as a natural analog and potential prodrug for more complex sialic acid derivatives. Sialic acids, or N-acetylneuraminic acids (NANA), are ubiquitously found on the surfaces of bacteria, viruses, and mammalian cells, playing pivotal roles in cell signaling, adhesion, and immune responses. The modification of sialic acid to produce 2-O-Methyl-beta-D-N-acetylneuraminic Acid enhances its stability and bioavailability, making it an attractive candidate for pharmaceutical formulations.

Recent advancements in synthetic chemistry have enabled the efficient production of 2-O-Methyl-beta-D-N-acetylneuraminic Acid, facilitating its incorporation into drug candidates targeting infectious diseases and inflammatory conditions. The compound’s ability to mimic natural sialic acid residues has been leveraged in the development of vaccines and antiviral agents. For instance, studies have demonstrated its potential in inhibiting viral entry by blocking receptor binding, particularly relevant in the context of influenza viruses where sialic acids serve as primary receptors.

The structural modifications introduced in 2-O-Methyl-beta-D-N-acetylneuraminic Acid contribute to its enhanced pharmacokinetic properties. Unlike free sialic acid, which is rapidly metabolized and excreted, the methylated derivative exhibits prolonged circulation time and reduced susceptibility to enzymatic degradation. This characteristic is particularly advantageous for therapeutic applications requiring sustained biological activity. Furthermore, the N-acetyl group at the 2-position imparts additional stability, preventing unwanted hydrolysis and improving shelf life.

Research into the pharmacological effects of 2-O-Methyl-beta-D-N-acetylneuraminic Acid has revealed promising results in modulating immune responses. Preclinical studies indicate that this compound can enhance antibody-dependent cellular cytotoxicity (ADCC) and natural killer (NK) cell activity, suggesting its potential use in immunotherapeutic strategies. Additionally, its ability to interfere with bacterial biofilm formation has been explored as a novel approach to combat antibiotic-resistant pathogens.

The synthesis of 2-O-Methyl-beta-D-N-acetylneuraminic Acid involves multi-step organic transformations that require precise control over reaction conditions to ensure high yield and purity. Advances in enzymatic catalysis have further refined these processes, allowing for greener and more sustainable production methods. The availability of scalable synthetic routes has made it feasible to incorporate this compound into clinical trials for various indications.

In conclusion, 2-O-Methyl-beta-D-N-acetylneuraminic Acid (CAS No. 23755-35-3) represents a significant advancement in glycoscience with broad implications for medicine and biotechnology. Its unique structural features enable diverse applications ranging from antiviral therapies to immunomodulation. As research continues to uncover new therapeutic potentials, this compound is poised to play an increasingly vital role in addressing global health challenges.

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