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N-Acetylmuramic acid 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 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 ^ 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.  See also Amino sugar Glucosamine v · d · eMicrobiology: Bacteria Pathogenic bacteria Bacterial disease · Coley's Toxins · Exotoxin · Lysogenic cycle Human flora Gut flora · Skin flora · Vaginal flora Substrate preference Lipophilic · Saccharophilic Oxygen preference Aerobic (Obligate) · Anaerobic (Facultative, Obligate) · Microaerophile · Nanaerobe · Aerotolerant Structures Cell envelope Cell membrane Cell wall: Peptidoglycan (NAM, NAG, DAP) Gram-positive bacteria only: Teichoic acid · Lipoteichoic acid · Endospore Gram-negative bacteria only: Bacterial outer membrane (Porin, Lipopolysaccharide) · Periplasmic space Mycobacteria only: Arabinogalactan · Mycolic acid Outside envelope Bacterial capsule · Slime layer · S-layer · Glycocalyx Pilus · Fimbria Composite Biofilm Shapes Bacterial cellular morphologies · L-form bacteria · Coccus (Diplococcus)  · Bacillus · Coccobacillus M: BAC bact (clas) gr+f/gr+a(t)/gr-p(c)/gr-o drug(J1p, w, n, m, vacc)