N-Acetylmuramic acid

N-Acetylmuramic acid
Identifiers
CAS number 10597-89-4 Y
PubChem 12917652
Properties
Molecular formula C11H19NO8
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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

Unlike most bacterial cell walls, Chlamydial cell wall lacks muramic acid. For this reason penicillin is not very effective in treating chlamydial infection. Protein synthesis blockers like doxycycline 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. doi:10.1093/jac/48.2.209. PMID 11481290. http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11481290. 

See also

Pathogenic bacteria
Human flora
Substrate preference
Oxygen preference
Structures
Outside envelope
Composite
Shapes

M: BAC

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)