N-Acetylmuramic acid (NAMorMurNAc) 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.
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| Names | |
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| IUPAC name
N-Acetylmuramic acid | |
| 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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| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.031.092 
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PubChem CID |
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| UNII | |
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). | |
NAM is an addition product of phosphoenolpyruvate and N-acetylglucosamine. This addition happens exclusively in the cell cytoplasm.
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.
