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{{short description|Chemical compound}} |
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{{distinguish|N-Acetylneuraminic acid}} |
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{{DISPLAYTITLE:''N''-Acetylmuramic acid}} |
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{{DISPLAYTITLE:''N''-Acetylmuramic acid}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 376306537 |
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| verifiedrevid = 443215358 |
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| Name=''N''-Acetylmuramic acid |
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| Name=''N''-Acetylmuramic acid |
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| ImageFile = N-Acetylmuramic acid.svg |
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| ImageFile = N-Acetylmuramic acid.svg |
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| ImageSize = 200 px |
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| ImageSize = 200 px |
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| IUPACName = |
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| IUPACName = ''N''-Acetylmuramic acid |
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| SystematicName = (2''R'')-2-<nowiki/>{oxy}propanoic acid |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 10597-89-4 |
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| PubChem = 12917652 |
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| CASNo = 10597-89-4 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| SMILES = |
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| UNII = 246FXU111L |
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| PubChem = 5462244 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4575341 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 21615 |
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| SMILES = O=C(O)(O1(O)(OC(O)1NC(=O)C)CO)C |
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| 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 |
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| InChIKey = MNLRQHMNZILYPY-MKFCKLDKBR |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = MNLRQHMNZILYPY-MKFCKLDKSA-N |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=11 | H=19 | N=1 | O=8 |
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| Formula = C<sub>11</sub>H<sub>19</sub>NO<sub>8</sub> |
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| MolarMass = |
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| MolarMass = |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPt = |
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| BoilingPt = |
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| Solubility = |
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| Solubility = |
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}} |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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| AutoignitionPt = |
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}} |
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}} |
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}} |
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}} |
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'''''N''-Acetylmuramic acid''', or '''MurNAc''', is the ] of ] and ] with a ] of ]<sub>11</sub>]<sub>19</sub>]]<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 ] residue of MurNAc. This layered structure is called ]. |
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'''''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 ] in most ]l ]s, which is built from alternating units of ] (GlcNAc) and ''N''-acetylmuramic acid, cross-linked by ]s at the ] residue of MurNAc. |
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==Formation of NAM== |
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MurNAc is a ] derivative of ]. |
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NAM is an addition product of ] and ''N''-acetylglucosamine. This addition happens exclusively in the cell ]. |
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==Clinical significance== |
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==Clinical significance== |
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''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 ]. 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. |
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Unlike most bacterial cell walls, ] cell wall lacks ]. For this reason ] is not very effective in treating chlamydial infection. ]s like ] or ] are used instead. |
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Synthesis is inhibited by ].<ref name="pmid11481290">{{cite journal |author=Grif K, Dierich MP, Pfaller K, Miglioli PA, Allerberger F |title=In vitro activity of fosfomycin in combination with various antistaphylococcal substances |journal=The Journal of antimicrobial chemotherapy |volume=48 |issue=2 |pages=209–17 |year=2001 |month=August |pmid=11481290 |doi= 10.1093/jac/48.2.209|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11481290}}</ref> |
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Synthesis of NAM is inhibited by ].<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=] |volume=48 |issue=2 |pages=209–217 |year=2001 |pmid=11481290 |doi= 10.1093/jac/48.2.209|doi-access=free }}</ref> |
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NAG and NAM cross-linking can be inhibited by ] to inhibit pathogens from growing within the body. Therefore, both NAG and NAM are valuable polymers in medicinal research. |
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==References== |
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==References== |
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