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N-Acetylmuramic acid: Wikis

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N-Acetylmuramic acid
N-Acetylmuramic acid.svg
Identifiers
CAS number 10597-89-4
Properties
Molecular formula C11H19NO8
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

Chlamydial cell wall lacks muramic acid. This is relevant because it is an exception, most bacteria have muramic acid in their cell walls. It is also clinically relevant. This is the reason penicillin is not very effective in treating chlamydial infection, a protein synthesis blocker like doxocyxline or azithromycin are used instead.

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". The Journal of antimicrobial chemotherapy 48 (2): 209–17. PMID 11481290. http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11481290.  

See also

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