N-Acetylmuramic acid 1110450 224438775 2008-07-08T21:06:35Z Arcadian 104523 /* Clinical significance */ wik {{Chembox new | ImageFile = MurNAc.gif | ImageSize = | IUPACName = | OtherNames = | Section1 = {{Chembox Identifiers | CASNo = 10597-89-4 | PubChem = | SMILES = }} | Section2 = {{Chembox Properties | Formula = C<sub>11</sub>H<sub>19</sub>NO<sub>8</sub> | MolarMass = | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | Autoignition = }} }} '''N-Acetylmuramic acid''', or '''MurNAc''', is the [[ether]] of [[lactic acid]] and [[N-acetylglucosamine]] with a [[chemical formula]] of [[Carbon|C]]<sub>11</sub>[[Hydrogen|H]]<sub>19</sub>[[Nitrogen|N]][[Oxygen|O]]<sub>8</sub>. 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== [[Chlamydia (bacterium)|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 chalmydial infection, a [[protein synthesis blocker]] like [[doxocyxline]] or [[azithromycin]] are used instead. ==See also== *[[Amino sugar]] *[[Glucosamine]] {{DEFAULTSORT:Acetylmuramic acid, N-}} [[Category:Amino sugars]] [[Category:Monosaccharide derivatives]] [[Category:Monosaccharides]] [[Category:Membrane biology]] {{orgchem-stub}} [[cs:Kyselina muramová]] [[ja:N-アセチルムラミン酸]]