N-Acetylmuramic acid

Not to be confused with N-Acetylneuraminic acid.
N-Acetylmuramic acid
Identifiers
10597-89-4 YesY
ChEBI CHEBI:21615 N
ChemSpider 4575341 N
Jmol 3D model Interactive image
PubChem 5462244
Properties
C11H19NO8
Molar mass 293.27 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

N-Acetylmuramic acid, or MurNAc, is the ether of lactic acid and N-acetylglucosamine with a chemical formula of C11H19NO8. It is part of a biopolymer in the bacterial cell wall, built from alternating units of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. This layered structure is called peptidoglycan.

MurNAc is a monosaccharide derivative of N-acetylglucosamine.

Clinical significance

N-Acetylmuramic acid (MURNAc) is part of the peptidoglycan polymer of Gram-positive bacterial cell walls. MURNAc is covalently linked to N-acetylglucosamine and may also be linked through the hydroxyl on carbon number 4 to the carbon of L-alanine (Figure 9.26). A pentapeptide composed of L-alanyl-d--isoglutaminyl-L-lysyl-D-alanine-D-alanine is added to the MURNAc in the process of making the peptidoglycan strands of the cell wall.

Synthesis is inhibited by fosfomycin.[1]

References

  1. ↑ Grif K, Dierich MP, Pfaller K, Miglioli PA, Allerberger F (August 2001). "In vitro activity of fosfomycin in combination with various antistaphylococcal substances". Journal of antimicrobial chemotherapy 48 (2): 209–17. doi:10.1093/jac/48.2.209. PMID 11481290.

See also

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