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CAS 10597-89-4

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N-Acetylmuramic acid

Description:
N-Acetylmuramic acid is a key component of bacterial cell walls, specifically found in peptidoglycan, which provides structural integrity to the cell. It is an amino sugar derivative of muramic acid, characterized by the presence of an acetyl group attached to the nitrogen atom of the amino group. This compound typically exists as a white to off-white crystalline powder and is soluble in water, reflecting its polar nature due to the presence of hydroxyl and amino groups. N-Acetylmuramic acid plays a crucial role in the biosynthesis of peptidoglycan, contributing to the rigidity and shape of bacterial cells. Its structure includes a lactyl group, which is essential for cross-linking with peptide chains, thereby enhancing the mechanical strength of the cell wall. In addition to its biological significance, N-acetylmuramic acid is of interest in research related to antibiotic development and the study of bacterial resistance mechanisms. Its CAS number, 10597-89-4, is used for identification in chemical databases and regulatory contexts.
Formula:C11H19NO8
InChI:InChI=1S/C11H19NO8/c1-5(11(18)19)20-10(9(17)8(16)4-14)7(3-13)12-6(2)15/h3,5,7-10,14,16-17H,4H2,1-2H3,(H,12,15)(H,18,19)/t5-,7+,8-,9-,10-/m1/s1
InChI key:InChIKey=SOARVSUSWULNDI-TVVSKHENSA-N
SMILES:[C@@H]([C@@H](NC(C)=O)C=O)([C@@H]([C@@H](CO)O)O)O[C@@H](C(O)=O)C
Synonyms:
  • N-Acetylmuramic acid
  • (+)-N-Acetylmuramic acid
  • Muramic acid, N-acetyl-
  • D-Glucose, 2-(acetylamino)-3-O-(1-carboxyethyl)-2-deoxy-, (R)-
  • D-Glucose, 2-acetamido-3-O-(D-1-carboxyethyl)-2-deoxy-
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