N-Acetylmuramic acid

2023-09-09T18:00:11Z

94.191.136.50: Removed sentence that did not make any sense

{{short description|Chemical compound}}
{{distinguish|N-Acetylneuraminic acid}}
{{DISPLAYTITLE:''N''-Acetylmuramic acid}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443215358
| Name=''N''-Acetylmuramic acid
| ImageFile = N-Acetylmuramic acid.svg
| ImageSize = 200 px
| IUPACName = ''N''-Acetylmuramic acid
| SystematicName = (2''R'')-2-<nowiki/>{[(2''R'',3''R'',4''R'',5''R'')-2-Acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxy}propanoic acid
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 10597-89-4
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 246FXU111L
| PubChem = 5462244
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4575341
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 21615
| SMILES = O=C(O)[C@H](O[C@H]1[C@H](O)[C@H](OC(O)[C@@H]1NC(=O)C)CO)C
| InChI = 1/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1
| InChIKey = MNLRQHMNZILYPY-MKFCKLDKBR
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = MNLRQHMNZILYPY-MKFCKLDKSA-N
}}
|Section2={{Chembox Properties
| C=11 | H=19 | N=1 | O=8
| MolarMass =
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}

'''''N''-Acetylmuramic acid''' ('''NAM''' or '''MurNAc''') is an organic compound with the chemical formula {{chem|C|11|H|19|N|O|8}}. It is a monomer of [[peptidoglycan]] in most [[bacteria]]l [[cell wall]]s, which is built from alternating units of [[N-Acetylglucosamine|''N''-acetylglucosamine]] (GlcNAc) and ''N''-acetylmuramic acid, cross-linked by [[oligopeptide]]s at the [[lactic acid]] residue of MurNAc.

==Formation of NAM==
NAM is an addition product of [[phosphoenolpyruvate]] and ''N''-acetylglucosamine. This addition happens exclusively in the cell [[cytoplasm]].

==Clinical significance==
''N''-Acetylmuramic acid (MurNAc) is part of the peptidoglycan polymer of bacterial cell walls. MurNAc is covalently linked to ''N''-acetylglucosamine and may also be linked through the hydroxyl on carbon number 4 to the carbon of [[L-alanine]]. A pentapeptide composed of L-alanyl-D-isoglutaminyl-L-lysyl-D-alanyl-D-alanine is added to the MurNAc in the process of making the peptidoglycan strands of the cell wall.

Synthesis of NAM is inhibited by [[fosfomycin]].<ref name="pmid11481290">{{cite journal |vauthors=Grif K, Dierich MP, Pfaller K, Miglioli PA, Allerberger F |title=''In vitro'' activity of fosfomycin in combination with various antistaphylococcal substances |journal=[[Journal of Antimicrobial Chemotherapy]] |volume=48 |issue=2 |pages=209–217 |year=2001 |pmid=11481290 |doi= 10.1093/jac/48.2.209|doi-access=free }}</ref>

NAG and NAM cross-linking can be inhibited by [[Antibiotic|antibiotics]] to inhibit pathogens from growing within the body. Therefore, both NAG and NAM are valuable polymers in medicinal research.

==References==
{{reflist}}

==See also==
*[[Amino sugar]]
*[[Glucosamine]]

{{Bacteria}}

{{DEFAULTSORT:Acetylmuramic acid, N-}}
[[Category:Amino sugars]]
[[Category:Monosaccharide derivatives]]
[[Category:Monosaccharides]]
[[Category:Membrane biology]]

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N-Acetylmuramic acid