N-Acetylmuramic acid
1110450
224438775
2008-07-08T21:06:35Z
Arcadian
104523
/* Clinical significance */ wik
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| CASNo = 10597-89-4
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| Section2 = {{Chembox Properties
| Formula = C<sub>11</sub>H<sub>19</sub>NO<sub>8</sub>
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'''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]]