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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

^ Grif K, Dierich MP, Pfaller K, Miglioli PA, Allerberger F (August 2001). "In vitro activity of fosfomycin in combination with various antistaphylococcal substances". Journal of antimicrobial chemotherapy 48 (2): 209–17. doi:10.1093/jac/48.2.209. PMID 11481290.

English Journal

Glycan sequence-dependent nod2 activation investigated by using a chemically synthesized bacterial peptidoglycan fragment library.

Wang N, Huang CY, Hasegawa M, Inohara N, Fujimoto Y, Fukase K.SourceDepartment of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043 (Japan).
Chembiochem : a European journal of chemical biology.Chembiochem.2013 Mar 4;14(4):482-8. doi: 10.1002/cbic.201200655. Epub 2013 Jan 29.
Nucleotide oligomerization domain-containing protein 2 (Nod2), an innate immune receptor, recognizes bacterial cell-wall peptidoglycan (PGN), the minimum ligand of which is muramyl dipeptide (MDP). Enzymatic digestion of PGN appears to be important for Nod2 recognition. PGN is degraded by muramidase
PMID 23362105

The biosynthesis of caprazamycins and related liponucleoside antibiotics: new insights.

Gust B, Eitel K, Tang X.SourceDepartment of Pharmceutical Biology, Pharmaceutical Institute, Eberhard Karls University Tübingen, Auf der Morgenstelle 8, D-72076 Tübingen, Germany. bertolt.gust@uni-tuebingen.de
Biological chemistry.Biol Chem.2013 Feb;394(2):251-9. doi: 10.1515/hsz-2012-0274.
The first step in the membrane cycle of reactions during peptidoglycan biosynthesis is the transfer of phospho-MurNAc-pentapeptide from UDP-MurNAc-pentapeptide to undecaprenyl phosphate, catalyzed by the integral membrane protein MraY translocase. Different MraY inhibitors are known and can be subdi
PMID 23104838

Efficient access to peptidyl-RNA conjugates for picomolar inhibition of non-ribosomal FemX(Wv) aminoacyl transferase.

Fonvielle M, Mellal D, Patin D, Lecerf M, Blanot D, Bouhss A, Santarem M, Mengin-Lecreulx D, Sollogoub M, Arthur M, Ethève-Quelquejeu M.SourceCentre de Recherche des Cordeliers, LRMA, Equipe 12, Université Pierre et Marie Curie - Paris 6, UMR S 872, Paris 75006, France.
Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2013 Jan 21;19(4):1357-63. doi: 10.1002/chem.201201999. Epub 2012 Nov 29.
Peptidyl-RNA conjugates have various applications in studying the ribosome and enzymes participating in tRNA-dependent pathways such as Fem transferases in peptidoglycan synthesis. Herein a convergent synthesis of peptidyl-RNAs based on Huisgen-Sharpless cycloaddition for the final ligation step is
PMID 23197408

Japanese Journal

Identification and Characterization of a Novel Polysaccharide Deacetylase C (PdaC) from Bacillus subtilis

Kobayashi Kaori,Sudiarta I. Putu,Kodama Takeko,Fukushima Tatsuya,Ara Katsutoshi,Ozaki Katsuya,Sekiguchi Junichi
JOURNAL OF BIOLOGICAL CHEMISTRY 287(13), 9765-9776, 2012-03-23
… subtilis peptidoglycan and its polymer, (-GlcNAc-MurNAc[-L-Ala-D-Glu]-)(n). … Surprisingly, RP-HPLC and ESI-MS/MS analyses showed that the enzyme deacetylates N-acetylmuramic acid (MurNAc) not GlcNAc from the polymer. … Therefore, PdaC has GlcNAc deacetylase activity toward GlcNAc oligomers and MurNAc deacetylase activity toward B. …
NAID 120005147954

抗メチシリン耐性黄色ブドウ球菌薬の開発研究

橋爪秀樹
YAKUGAKU ZASSHI 132(1), 59-67, 2012
… Studies of incorporation of radioactive macromolecular precursors and accumulation of UDP-MurNAc-pentapeptide in the cytoplasm in S. …
NAID 130001871963

The functional effect of Gly209 and Ile213 substitutions on lysozyme activity of family 19 chitinase encoded by cyanophage Ma-LMM01

Hosoda Naohiko,Kurokawa Yoichi,Sako Yoshihiko,Nagasaki Keizo,Yoshida Takashi,Hiroishi Shingo
Fisheries Science 77(4), 665-670, 2011-07
… whereas lysozymes hydrolyzes peptidoglycan, alternating β-1, 4-linked copolymers of N-acetylmuramic acid (MurNAc) and GlcNAc. … The data suggest the Ile213 residue is involved in recognizing the substrate MurNAc; …
NAID 80021849888

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★リンクテーブル★

リンク元	「ペプチドグリカン」

「ペプチドグリカン」

N-Acetylmuramic acid
Identifiers
CAS number	10597-89-4
PubChem	5462244
ChemSpider	4575341
ChEBI	CHEBI:21615
Jmol-3D images	Image 1
	SMILES O=C(O)[C@H](O[C@H]1[C@H](O)[C@H](OC(O)[C@@H]1NC(=O)C)CO)C ;
	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 ; Key: MNLRQHMNZILYPY-MKFCKLDKSA-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 ;
Properties
Molecular formula	C11H19NO8
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

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英: peptidoglycan
同: ムレイン murein
関

細菌の細胞壁成分
グラム陽性菌には厚く、グラム陰性菌には薄く存在する
N-アセチルグルコサミン(NAG, GlcNAc)、N-アセチルムラミン酸(NAM, MurNAc)が直鎖状に連結。この鎖にNAM+L-Ala+D-Glu+L-Lys+D-Ala+NAM?

[pmid11481290-1] Grif K, Dierich MP, Pfaller K, Miglioli PA, Allerberger F (August 2001). "In vitro activity of fosfomycin in combination with various antistaphylococcal substances". Journal of antimicrobial chemotherapy 48 (2): 209–17. doi:10.1093/jac/48.2.209. PMID 11481290.

匿名

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案内

案内

MurNAc