N-Acetylmuramic acid

N-Acetylmuramic acid

Identifiers
CAS Number	10597-89-4 Y
ChEBI	CHEBI:21615 N
ChemSpider	4575341 N
Jmol interactive 3D	Image
PubChem	5462244
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
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, or MurNAc, is the ether of lactic acid and N-acetylglucosamine with a chemical formula of C₁₁H₁₉NO₈. It is part of a biopolymer in the bacterial cell wall, 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.

MurNAc is a monosaccharide derivative of N-acetylglucosamine.

Clinical significance

Unlike most bacterial cell walls, Chlamydial cell wall lacks muramic acid. For this reason penicillin is not very effective in treating chlamydial infection. Protein synthesis blockers like doxycycline or azithromycin are used instead.

N-Acetylmuramic acid (MURNAc) is part of the peptidoglycan polymer of Gram-positive 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 (Figure 9.26). A pentapeptide composed of L-alanyl-d--isoglutaminyl-L-lysyl-D-alanine-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

See also

• Amino sugar
• Glucosamine