2.02012-05-31 14:31:32 -06002015-06-03 17:19:28 -0600ECMDB20176M2MDB001023N-Acetyl-D-muramoateN-acetyl-D-muramoate is a member of the chemical class known as Sugar Acids and Derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group. UDP-N-acetylmuramic acid (UDP-MurNAc) is a precursor for peptidoglycan biosynthesis in bacteria. (PMID 14659546) Peptidoglycan is the major constituent of the cell wall, which is comprised of backbone repeats of N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM). (PMID 18700763) UDP-N-acetylmuramic acid (UDP-MurNAc) is a potent inhibitor of MurA (enolpyruvyl-UDP-GlcNAc synthase). (PMID 15751977) The bacterial cell wall is a polymer consisting of alternating N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) units, cross-linked via peptides appended to MurNAc. (PMID 12369847). The peptidoglycan synthesis pathway starts at the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-alpha-D-glucosamine, yielding the complete monomeric unit a lipid , also known as lipid . This final lipid intermediate is transferred through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks.N-Acetyl-D-muramoic acidN-AcetylmuramateN-Acetylmuramic acidC11H19NO8293.2705293.111066589(2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid(2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid61633-75-8[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(O)[C@]1([H])N=C(C)O)C(O)=OInChI=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/s1MNLRQHMNZILYPY-MKFCKLDKSA-NExtra-organismPeriplasmlogp-1.75logs-0.74solubility5.36e+01 g/llogp-1.7pka_strongest_acidic3.55pka_strongest_basic1.39iupac(2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acidaverage_mass293.2705mono_mass293.111066589smiles[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(O)[C@]1([H])N=C(C)O)C(O)=OformulaC11H19NO8inchiInChI=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/s1inchikeyMNLRQHMNZILYPY-MKFCKLDKSA-Npolar_surface_area149.04refractivity62.88polarizability27.39rotatable_bond_count5acceptor_count9donor_count5physiological_charge-1formal_charge0Amino sugar and nucleotide sugar metabolismec00520Phosphotransferase system (PTS)ec02060Specdb::CMs35568Specdb::CMs48249Specdb::CMs169125Specdb::NmrOneD59292Specdb::NmrOneD59293Specdb::NmrOneD59294Specdb::NmrOneD59295Specdb::NmrOneD59296Specdb::NmrOneD59297Specdb::NmrOneD59298Specdb::NmrOneD59299Specdb::NmrOneD59300Specdb::NmrOneD59301Specdb::NmrOneD59302Specdb::NmrOneD59303Specdb::NmrOneD59304Specdb::NmrOneD59305Specdb::NmrOneD59306Specdb::NmrOneD59307Specdb::NmrOneD59308Specdb::NmrOneD59309Specdb::NmrOneD59310Specdb::NmrOneD59311Specdb::MsMs24461Specdb::MsMs24462Specdb::MsMs24463Specdb::MsMs31019Specdb::MsMs31020Specdb::MsMs31021Specdb::MsMs437304Specdb::MsMs437305Specdb::MsMs437306Specdb::MsMs437307Specdb::MsMs437308Specdb::MsMs445746Specdb::MsMs445747Specdb::MsMs445748Specdb::MsMs445749Specdb::MsMs445750Specdb::MsMs2236330Specdb::MsMs2237071Specdb::MsMs2238460Specdb::MsMs2239098Specdb::MsMs2240588Specdb::MsMs2241130Specdb::MsMs2242621Specdb::MsMs2243211Specdb::MsMs224880154622444575341C0271321615Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Suvorov, M., Lee, M., Hesek, D., Boggess, B., Mobashery, S. (2008). "Lytic transglycosylase MltB of Escherichia coli and its role in recycling of peptidoglycan strands of bacterial cell wall." J Am Chem Soc 130:11878-11879.18700763Mizyed, S., Oddone, A., Byczynski, B., Hughes, D. W., Berti, P. J. (2005). "UDP-N-acetylmuramic acid (UDP-MurNAc) is a potent inhibitor of MurA (enolpyruvyl-UDP-GlcNAc synthase)." Biochemistry 44:4011-4017.15751977Schwartz, B., Markwalder, J. A., Seitz, S. P., Wang, Y., Stein, R. L. (2002). "A kinetic characterization of the glycosyltransferase activity of Eschericia coli PBP1b and development of a continuous fluorescence assay." Biochemistry 41:12552-12561.12369847Raymond, J. B., Price, N. P., Pavelka, M. S. Jr (2003). "A method for the enzymatic synthesis and HPLC purification of the peptidoglycan precursor UDP-N-acetylmuramic acid." FEMS Microbiol Lett 229:83-89.14659546Phosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlN-acetylmuramoyl-L-alanine amidase AmiBP26365AMIB_ECOLIamiBhttp://ecmdb.ca/proteins/P26365.xmlProbable N-acetylmuramoyl-L-alanine amidase AmiAP36548AMIA_ECOLIamiAhttp://ecmdb.ca/proteins/P36548.xmlN-acetylmuramoyl-L-alanine amidase AmiCP63883AMIC_ECOLIamiChttp://ecmdb.ca/proteins/P63883.xmlGlucose-specific phosphotransferase enzyme IIA componentP69783PTGA_ECOLIcrrhttp://ecmdb.ca/proteins/P69783.xmlPTS system N-acetylmuramic acid-specific EIIBC componentP77272PTYBC_ECOLImurPhttp://ecmdb.ca/proteins/P77272.xmlPhosphocarrier protein HPrP0AA04PTHP_ECOLIptsHhttp://ecmdb.ca/proteins/P0AA04.xmlPTS system N-acetylmuramic acid-specific EIIBC componentP77272PTYBC_ECOLImurPhttp://ecmdb.ca/proteins/P77272.xmlSugar efflux transporter CP31436SETC_ECOLIsetChttp://ecmdb.ca/proteins/P31436.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlPhosphoenolpyruvic acid + N-Acetyl-D-muramoate > N-Acetylmuramic acid 6-phosphate + Pyruvic acidN-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-AlanineR04112N-Acetyl-D-muramoate + Protein N(pi)-phospho-L-histidine <> N-Acetylmuramic acid 6-phosphate + Protein histidineR08559N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-AlanineN-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine