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N-Acetylmuramic acid

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Chemical compound

Not to be confused withN-Acetylneuraminic acid.

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
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 theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

N-Acetylmuramic acid (NAM orMurNAc) is an organic compound with the chemical formulaC
₁₁H
₁₉NO
₈. It is a monomer ofpeptidoglycan in mostbacterial cell walls, which is built from alternating units ofN-acetylglucosamine (GlcNAc) andN-acetylmuramic acid, cross-linked byoligopeptides at thelactic acid residue of MurNAc.

Formation of NAM

[edit]

NAM is an addition product ofphosphoenolpyruvate andN-acetylglucosamine. This addition happens exclusively in the cellcytoplasm.

Clinical significance

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N-Acetylmuramic acid (MurNAc) is part of the peptidoglycan polymer of bacterial cell walls. MurNAc is covalently linked toN-acetylglucosamine and may also be linked through the hydroxyl on carbon number 4 to the carbon ofL-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 byfosfomycin.^[1]

NAG and NAM cross-linking can be inhibited byantibiotics to inhibit pathogens from growing within the body. Therefore, both NAG and NAM are valuable polymers in medicinal research.

References

[edit]

^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.

Oxygen preference	Aerobic Obligate Facultative Anaerobic Facultative Obligate Microaerophile Nanaerobe Aerotolerant
Other	Extremophile Human microbiome Gut Lung Mouth Skin Vaginal (in pregnancy) Placental Uterine Salivary Microbial metabolism Nitrogen fixation Microbial ecology Primary nutritional groups Substrate preference Lipophilic Saccharophilic

Shape

Structure

Cell envelope	Cell membrane Cell wall:Peptidoglycan NAM NAG DAP Gram-positive bacteria only:Teichoic acid Lipoteichoic acid Endospore Gram-negative bacteria only:Bacterial outer membrane Porin Lipopolysaccharide Periplasmic space Mycobacteria only:Arabinogalactan Mycolic acid
Outside envelope	Bacterial capsule Slime layer S-layer Glycocalyx Pilus Fimbria Non-motile bacteria
Composite	Biofilm

Taxonomy
andevolution

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Formation of NAM

Clinical significance

References

See also