N-Acetylmuramic acid
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| IUPAC name
N-Acetylmuramic acid
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| Systematic IUPAC name
(2R)-2-{[(2R,3R,4R,5R)-2-Acetamido-4,5,6-trihydroxy-1-oxohexan-3-yl]oxy}propanoic acid | |
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3D model (JSmol)
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| ECHA InfoCard | 100.031.092 Edit this at Wikidata |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C11H19NO8 | |
| Molar mass | 293.272 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Acetylmuramic acid (NAM or MurNAc) is an organic compound with the chemical formula C
11H
19NO
8. It is a monomer of peptidoglycan in most bacterial cell walls, which is built from alternating units of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid, cross-linked by oligopeptides at the lactic acid residue of MurNAc.
Formation of NAM
[edit ]NAM is an addition product of phosphoenolpyruvate and N-acetylglucosamine. This addition happens exclusively in the cell cytoplasm.
Clinical significance
[edit ]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.[1]
NAG and NAM cross-linking can be inhibited by antibiotics to inhibit pathogens from growing within the body. Therefore, both NAG and NAM are valuable polymers in medicinal research.
References
[edit ]- ^ Grif K, Dierich MP, Pfaller K, Miglioli PA, Allerberger F (2001). "In vitro activity of fosfomycin in combination with various antistaphylococcal substances". Journal of Antimicrobial Chemotherapy . 48 (2): 209–217. doi:10.1093/jac/48.2.209 . PMID 11481290.