N-Acetylmuramic acid

N-Acetylmuramic acid, "NAM" or MurNAc, is the addition of phosphoenolpyruvate and N-acetylglucosamine with the chemical formula C
11H
19NO
8. It is a key builder of peptidoglycan in the bacterial cell wall, which is built from alternating units of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc), cross-linked by oligopeptides at the lactic acid residue of MurNAc.

Not to be confused with N-Acetylneuraminic acid.
N-Acetylmuramic acid
Names
Preferred IUPAC name
(2R)-2-{[(2R,3R,4R,5S,6R)-3-Acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-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

MurNAc is a monosaccharide derivative of N-acetylglucosamine.

Formation of NAM

NAM is a combination of N-acetylglucosamine and phosphoenolpyruvate (PEP). 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 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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