N-Acetylmuramic acid
Names
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
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.031.092
UNII
  • InChI=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 ☒N
    Key: MNLRQHMNZILYPY-MKFCKLDKSA-N ☒N
  • 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
    Key: MNLRQHMNZILYPY-MKFCKLDKBR
  • O=C(O)[C@H](O[C@H]1[C@H](O)[C@H](OC(O)[C@@H]1NC(=O)C)CO)C
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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Infobox references

N-Acetylmuramic acid (NAM or MurNAc) is an organic compound with the chemical formula C
11
H
19
NO
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

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.[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

  1. 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.

See also

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