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Chemical Compound Review

CHEBI:47970     (2R)-2-[(2R,3R,4R,5R)-2- amino-4,5,6...

Synonyms: AC1L3OZV, Ambap1114-41-6, EINECS 214-214-9
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Disease relevance of Muramic acid


Psychiatry related information on Muramic acid


High impact information on Muramic acid

  • The sensitivity of GC-MS to detect muramic acid was 2 pg/injected amount (227 pg muramic acid/mg ST), and that of the pan-bacterial PCR was 2-20 bacteria colony forming units/reaction [4].
  • To identify the pattern recognition domains of CCF, deletion mutants were tested for their ability to reconstitute the prophenoloxidase cascade in E. foetida coelomic fluid depleted of endogenous CCF in the presence of LPS, beta-1,3-glucans, N,N'-diacetylchitobiose, and muramic acid [2].
  • Muramic acid from the synovial fluid was studied by gas chromatography-mass spectrometry [7].
  • Mass spectrometric quantitation of muramic acid, a bacterial cell wall component, in septic synovial fluids [3].
  • We report that in both peptidoglycans, the minimal structure needed to activate the Toll pathway is a muropeptide dimer and that the free reducing end of the N-acetyl muramic acid residues of the muropeptides is essential for activity [8].

Chemical compound and disease context of Muramic acid


Biological context of Muramic acid

  • Unlike endotoxin, muramic acid was inversely associated with wheezing rather than with atopic sensitization [14].
  • The 6-O acetylation of muramic acid enhanced the somnogenic effects of certain monomeric MPs relative to their non-O-acetylated (but otherwise identical) counterparts [15].
  • Muramic acid as a measure of microbial biomass in estuarine and marine samples [16].
  • A reproducible assay involving acid hydrolysis, preparative thin-layer chromatographic purification, and colorimetric analysis of lactate released from muramic acid by alkaline hydrolysis is described [16].
  • Strain IAM 14817(T) (=NCIMB 9991(T)) has the following characteristics: the predominant menaquinones are MK-9 and MK-10, the DNA G+C content is 68 mol%, the diamino acid in the cell wall is 2,4-l-diaminobutyric acid and the muramic acid in the peptidoglycan is of an acetyl type [17].

Anatomical context of Muramic acid


Associations of Muramic acid with other chemical compounds


Gene context of Muramic acid


Analytical, diagnostic and therapeutic context of Muramic acid


  1. Chimeric phage-bacterial enzymes: a clue to the modular evolution of genes. Díaz, E., López, R., García, J.L. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  2. Distinct carbohydrate recognition domains of an invertebrate defense molecule recognize Gram-negative and Gram-positive bacteria. Bilej, M., De Baetselier, P., Van Dijck, E., Stijlemans, B., Colige, A., Beschin, A. J. Biol. Chem. (2001) [Pubmed]
  3. Mass spectrometric quantitation of muramic acid, a bacterial cell wall component, in septic synovial fluids. Christensson, B., Gilbart, J., Fox, A., Morgan, S.L. Arthritis Rheum. (1989) [Pubmed]
  4. Bacterial components in the synovial tissue of patients with advanced rheumatoid arthritis or osteoarthritis: analysis with gas chromatography-mass spectrometry and pan-bacterial polymerase chain reaction. Chen, T., Rimpiläinen, M., Luukkainen, R., Möttönen, T., Yli-Jama, T., Jalava, J., Vainio, O., Toivanen, P. Arthritis Rheum. (2003) [Pubmed]
  5. Muramic acid is not detectable in Chlamydia psittaci or Chlamydia trachomatis by gas chromatography-mass spectrometry. Fox, A., Rogers, J.C., Gilbart, J., Morgan, S., Davis, C.H., Knight, S., Wyrick, P.B. Infect. Immun. (1990) [Pubmed]
  6. Bacterial peptidoglycans as modulators of sleep. II. Effects of muramyl peptides on the structure of rabbit sleep. Krueger, J.M., Davenne, D., Walter, J., Shoham, S., Kubillus, S.L., Rosenthal, R.S., Martin, S.A., Biemann, K. Brain Res. (1987) [Pubmed]
  7. Salmonella-triggered reactive arthritis: use of polymerase chain reaction, immunocytochemical staining, and gas chromatography-mass spectrometry in the detection of bacterial components from synovial fluid. Nikkari, S., Rantakokko, K., Ekman, P., Möttönen, T., Leirisalo-Repo, M., Virtala, M., Lehtonen, L., Jalava, J., Kotilainen, P., Granfors, K., Toivanen, P. Arthritis Rheum. (1999) [Pubmed]
  8. Requirements of peptidoglycan structure that allow detection by the Drosophila Toll pathway. Filipe, S.R., Tomasz, A., Ligoxygakis, P. EMBO Rep. (2005) [Pubmed]
  9. Structural analysis of Bacillus megaterium KM spore peptidoglycan and its dynamics during germination. Atrih, A., Bacher, G., Körner, R., Allmaier, G., Foster, S.J. Microbiology (Reading, Engl.) (1999) [Pubmed]
  10. Thermobaculum terrenum gen. nov., sp. nov.: a non-phototrophic gram-positive thermophile representing an environmental clone group related to the Chloroflexi (green non-sulfur bacteria) and Thermomicrobia. Botero, L.M., Brown, K.B., Brumefield, S., Burr, M., Castenholz, R.W., Young, M., McDermott, T.R. Arch. Microbiol. (2004) [Pubmed]
  11. Association between exposure to farming, allergies and genetic variation in CARD4/NOD1. Eder, W., Klimecki, W., Yu, L., von Mutius, E., Riedler, J., Braun-Fahrländer, C., Nowak, D., Holst, O., Martinez, F.D. Allergy (2006) [Pubmed]
  12. Structure of a muramic acid containing capsular polysaccharide from the pathogenic strain of Vibrio vulnificus ATCC 27562. Gunawardena, S., Reddy, G.P., Wang, Y., Kolli, V.S., Orlando, R., Morris, J.G., Bush, C.A. Carbohydr. Res. (1998) [Pubmed]
  13. Use of mass spectrometry for characterising microbial communities in bioaerosols. Szponar, B., Larsson, L. Annals of agricultural and environmental medicine : AAEM. (2001) [Pubmed]
  14. Microbial exposure of rural school children, as assessed by levels of N-acetyl-muramic acid in mattress dust, and its association with respiratory health. van Strien, R.T., Engel, R., Holst, O., Bufe, A., Eder, W., Waser, M., Braun-Fahrländer, C., Riedler, J., Nowak, D., von Mutius, E. J. Allergy Clin. Immunol. (2004) [Pubmed]
  15. Somnogenic activity of O-acetylated and dimeric muramyl peptides. Johannsen, L., Rosenthal, R.S., Martin, S.A., Cady, A.B., Obal, F., Guinand, M., Krueger, J.M. Infect. Immun. (1989) [Pubmed]
  16. Muramic acid as a measure of microbial biomass in estuarine and marine samples. King, J.D., White, D.C. Appl. Environ. Microbiol. (1977) [Pubmed]
  17. Plantibacter auratus sp. nov., in the family Microbacteriaceae. Lin, Y.C., Yokota, A. Int. J. Syst. Evol. Microbiol. (2006) [Pubmed]
  18. Failure To detect muramic acid in normal rat tissues but detection in cerebrospinal fluids from patients with Pneumococcal meningitis. Kozar, M.P., Krahmer, M.T., Fox, A., Gray, B.M. Infect. Immun. (2000) [Pubmed]
  19. Muramic acid in peripheral blood leukocytes of healthy human subjects. Lehtonen, L., Eerola, E., Oksman, P., Toivanen, P. J. Infect. Dis. (1995) [Pubmed]
  20. Detection of muramic acid in a carbohydrate fraction of human spleen. Hoijer, M.A., Melief, M.J., van Helden-Meeuwsen, C.G., Eulderink, F., Hazenberg, M.P. Infect. Immun. (1995) [Pubmed]
  21. Isolation and characterization of the outer membrane and lipopolysaccharide from Eikenella corrodens. Progulske, A., Holt, S.C. Infect. Immun. (1984) [Pubmed]
  22. Chemical composition and biological functions of Listeria monocytogenes cell wall preparations. Hether, N.W., Campbell, P.A., Baker, L.A., Jackson, L.L. Infect. Immun. (1983) [Pubmed]
  23. Elimination of group A streptococcal cell walls from mammalian tissues. Gilbart, J., Fox, A. Infect. Immun. (1987) [Pubmed]
  24. On-line sample preconcentration with chemical derivatization of bacterial biomarkers by capillary electrophoresis: a dual strategy for integrating sample pretreatment with chemical analysis. Ptolemy, A.S., Le Bihan, M., Britz-McKibbin, P. Electrophoresis (2005) [Pubmed]
  25. Electrospray tandem mass spectrometry for analysis of native muramic acid in whole bacterial cell hydrolysates. Black, G.E., Fox, A., Fox, K., Snyder, A.P., Smith, P.B. Anal. Chem. (1994) [Pubmed]
  26. Why are pathogenic staphylococci so lysozyme resistant? The peptidoglycan O-acetyltransferase OatA is the major determinant for lysozyme resistance of Staphylococcus aureus. Bera, A., Herbert, S., Jakob, A., Vollmer, W., Götz, F. Mol. Microbiol. (2005) [Pubmed]
  27. The Staphylococcus aureus receptor for fibronectin. Bibel, D.J., Aly, R., Shinefield, H.R., Maibach, H.I. J. Invest. Dermatol. (1983) [Pubmed]
  28. Biochemical properties of the outer membrane of Treponema denticola. Yotis, W.W., Sharma, V.K., Gopalsami, C., Chegini, S., McNulty, J., Hoerman, K., Keene, J., Simonson, L.G. J. Clin. Microbiol. (1991) [Pubmed]
  29. Amperometric detection of muramic acid in high-performance liquid chromatography with a post-column reaction. Watanabe, N. J. Chromatogr. (1984) [Pubmed]
  30. Mucin secretion in germfree rats fed fiber-free and psyllium diets and bacterial mass and carbohydrate fermentation after colonization. Cabotaje, L.M., Shinnick, F.L., Lopéz-Guisa, J.M., Marlett, J.A. Appl. Environ. Microbiol. (1994) [Pubmed]
  31. Analysis of peptidoglycan structure from vegetative cells of Bacillus subtilis 168 and role of PBP 5 in peptidoglycan maturation. Atrih, A., Bacher, G., Allmaier, G., Williamson, M.P., Foster, S.J. J. Bacteriol. (1999) [Pubmed]
  32. A urinary marker for occult systemic coccal disease. Hyman, E.S. Nephron (1994) [Pubmed]
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