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N-Acetylneuraminic Acid Methyl Ester (CAS 22900-11-4)

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Alternate Names:
Methyl 5-Acetamido-3,5-dideoxy-beta-D-glycero-D-galacto-2-nonulopyranosylonate
Application:
N-Acetylneuraminic Acid Methyl Ester is derivative of Neuraminic Acid
CAS Number:
22900-11-4
Molecular Weight:
323.30
Molecular Formula:
C12H21NO9
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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N-Acetylneuraminic Acid Methyl Ester is a methylated derivative of N-acetylneuraminic acid (Neu5Ac), a predominant form of sialic acid involved in numerous biological functions, particularly in cell surface glycoconjugates. This modified compound is extensively utilized in biochemical research to study sialic acid biology without the complications of managing the highly polar and reactive carboxyl group found in native sialic acids. The methyl ester modification at the carboxylic acid group enhances the compound′s stability and makes it more lipophilic, facilitating its use in various experimental settings, including enzymatic assays and synthetic chemistry applications. Researchers employ N-Acetylneuraminic Acid Methyl Ester to investigate the enzymatic pathways involved in the catabolism and anabolism of sialic acids, which are crucial for understanding cellular recognition, viral infection mechanisms, and intercellular communication. This chemical is particularly valuable in the synthesis of sialylated oligosaccharides in a more controlled manner, enabling studies on how these complex sugars influence biological processes such as immune response and cell adhesion. The insights gained from such research are critical for advancing our understanding of glycoscience.


N-Acetylneuraminic Acid Methyl Ester (CAS 22900-11-4) References

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  2. Determination of sialic acids by liquid chromatography-mass spectrometry.  |  Shaw, CJ., et al. 2001. J Chromatogr A. 913: 365-70. PMID: 11355834
  3. Separation methods for sialic acids and critical evaluation of their biologic relevance.  |  Lamari, FN. and Karamanos, NK. 2002. J Chromatogr B Analyt Technol Biomed Life Sci. 781: 3-19. PMID: 12450650
  4. A simple synthesis of N-perfluoroacylated and N-acylated glycals of neuraminic acid with a cyclic aminic substituent at the 4α position as possible inhibitors of sialidases.  |  Rota, P., et al. 2012. Org Biomol Chem. 10: 2885-94. PMID: 22395901
  5. Quantitative determination and confirmatory analysis of N-acetylneuraminic and N-glycolylneuraminic acids in serum and urine by solid-phase extraction on-line coupled to liquid chromatography-tandem mass spectrometry.  |  Priego-Capote, F., et al. 2014. J Chromatogr A. 1346: 88-96. PMID: 24800968
  6. 2,3-Dehydro-4-epi-N-acetylneuraminic acid; a neuraminidase inhibitor.  |  Kumar, V., et al. 1981. Carbohydr Res. 94: 123-30. PMID: 7273035
  7. Synthesis of transition-state analogues as potential inhibitors of sialidase from Influenza virus.  |  Driguez, PA., et al. 1994. Carbohydr Res. 262: 297-310. PMID: 7982221
  8. The crystal structure of N-acetylneuraminic acid methyl ester monohydrate.  |  O'Connell, A. M. 1973. Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 29.11: 2320-2328.
  9. Structural variations on N‐acetylneuraminic acid, 16. A convenient approach to 3‐deoxy‐d‐glycero‐d‐galacto‐nonulosonic acid (KDN), 5‐azido‐5‐deoxy‐KDN and 5‐deoxy‐KDN, and their 4‐methylumbelliferyl 2α‐glycosides.  |  Schreiner, et al. 1990. Liebigs Annalen der Chemie. 1990.6: 581-586.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

N-Acetylneuraminic Acid Methyl Ester, 250 mg

sc-212110
250 mg
$290.00