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CAS 22900-11-4

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β-Neuraminic acid, N-acetyl-, methyl ester

Description:
β-Neuraminic acid, N-acetyl-, methyl ester, commonly referred to as a sialic acid derivative, is a naturally occurring compound that plays a significant role in cellular recognition and signaling processes. This compound is characterized by its structure, which includes a nine-carbon backbone with a carboxylic acid group, an acetamido group, and a methyl ester functional group. It is typically found in glycoproteins and glycolipids on the surfaces of cells, contributing to various biological functions, including immune response and pathogen recognition. The methyl ester form enhances its solubility and stability, making it useful in biochemical research and applications. β-Neuraminic acid derivatives are also important in the study of viral infections, as many viruses exploit sialic acids for cell entry. In terms of physical properties, it is generally a white to off-white solid, soluble in polar solvents, and exhibits characteristic UV absorbance. Its reactivity is influenced by the presence of functional groups, allowing for further chemical modifications in synthetic applications.
Formula:C12H21NO9
InChI:InChI=1/C12H21NO9/c1-5(15)13-8-6(16)3-12(20,11(19)21-2)22-10(8)9(18)7(17)4-14/h6-10,14,16-18,20H,3-4H2,1-2H3,(H,13,15)/t6-,7+,8+,9+,10+,12-/m0/s1
InChI key:InChIKey=BKZQMWNJESHHSA-AGNBLMTLSA-N
SMILES:[C@H]([C@@H](CO)O)(O)[C@]1([C@H](NC(C)=O)[C@@H](O)C[C@](C(OC)=O)(O)O1)[H]
Synonyms:
  • <span class="text-smallcaps">D</smallcap>-glycero-<smallcap>D</span>-galacto-Nonulopyranosonic acid, 5-acetamido-3,5-dideoxy-, methyl ester, β-
  • <span class="text-smallcaps">D</smallcap>-glycero-β-<smallcap>D</span>-galacto-2-Nonulopyranosonic acid, 5-(acetylamino)-3,5-dideoxy-, methyl ester
  • Methyl (6R)-5-acetamido-3,5-dideoxy-6-[(2R)-1,2,3-trihydroxypropyl]-alpha-L-threo-hex-2-ulopyranosonate
  • Methyl N-acetyl-β-neuraminate
  • N-Acetyl-β-neuraminic acid methyl ester
  • β-Neuraminic acid, N-acetyl-, methyl ester
  • D-glycero-β-D-galacto-2-Nonulopyranosonic acid, 5-(acetylamino)-3,5-dideoxy-, methyl ester
  • D-glycero-D-galacto-Nonulopyranosonic acid, 5-acetamido-3,5-dideoxy-, methyl ester, β-
  • -1,2,3-trihydroxypropyl)
  • (2S,4S,5R,6R)-Methyl 5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylate
  • See more synonyms
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