N-Acetylmuramic acid

N-Acetylmuramic acid, or MurNAc, is the ether of lactic acid and N-acetylglucosamine with the chemical formula C
₁₁H
₁₉NO
₈. It is part of a biopolymer in the bacterial cell wall, which is built from alternating units of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. This layered structure is called peptidoglycan.

Not to be confused with N-Acetylneuraminic acid.

N-Acetylmuramic acid

Identifiers
CAS Number	10597-89-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:21615^N
ChemSpider	4575341^N
ECHA InfoCard	100.031.092
PubChem CID	5462244
UNII	246FXU111L^N
CompTox Dashboard (EPA)	DTXSID70893663
InChI 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
SMILES O=C(O)[C@H](O[C@H]1[C@H](O)[C@H](OC(O)[C@@H]1NC(=O)C)CO)C
Properties
Chemical formula	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).
N verify (what is ^YN ?)
Infobox references

MurNAc is a monosaccharide derivative of N-acetylglucosamine.

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]

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

• Amino sugar
• Glucosamine