2.0 2012-05-31 14:31:32 -0600 2015-06-03 17:19:28 -0600 ECMDB20176 M2MDB001023 N-Acetyl-D-muramoate N-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 acid N-Acetylmuramate N-Acetylmuramic acid C11H19NO8 293.2705 293.111066589 (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 acid 61633-75-8 [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)=O 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 MNLRQHMNZILYPY-MKFCKLDKSA-N Extra-organism Periplasm logp -1.75 ALOGPS logs -0.74 ALOGPS solubility 5.36e+01 g/l ALOGPS logp -1.7 ChemAxon pka_strongest_acidic 3.55 ChemAxon pka_strongest_basic 1.39 ChemAxon iupac (2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid ChemAxon average_mass 293.2705 ChemAxon mono_mass 293.111066589 ChemAxon smiles [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)=O ChemAxon formula C11H19NO8 ChemAxon 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 ChemAxon inchikey MNLRQHMNZILYPY-MKFCKLDKSA-N ChemAxon polar_surface_area 149.04 ChemAxon refractivity 62.88 ChemAxon polarizability 27.39 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Amino sugar and nucleotide sugar metabolism ec00520 Phosphotransferase system (PTS) ec02060 Specdb::CMs 35568 Specdb::CMs 48249 Specdb::CMs 169125 Specdb::NmrOneD 59292 Specdb::NmrOneD 59293 Specdb::NmrOneD 59294 Specdb::NmrOneD 59295 Specdb::NmrOneD 59296 Specdb::NmrOneD 59297 Specdb::NmrOneD 59298 Specdb::NmrOneD 59299 Specdb::NmrOneD 59300 Specdb::NmrOneD 59301 Specdb::NmrOneD 59302 Specdb::NmrOneD 59303 Specdb::NmrOneD 59304 Specdb::NmrOneD 59305 Specdb::NmrOneD 59306 Specdb::NmrOneD 59307 Specdb::NmrOneD 59308 Specdb::NmrOneD 59309 Specdb::NmrOneD 59310 Specdb::NmrOneD 59311 Specdb::MsMs 24461 Specdb::MsMs 24462 Specdb::MsMs 24463 Specdb::MsMs 31019 Specdb::MsMs 31020 Specdb::MsMs 31021 Specdb::MsMs 437304 Specdb::MsMs 437305 Specdb::MsMs 437306 Specdb::MsMs 437307 Specdb::MsMs 437308 Specdb::MsMs 445746 Specdb::MsMs 445747 Specdb::MsMs 445748 Specdb::MsMs 445749 Specdb::MsMs 445750 Specdb::MsMs 2236330 Specdb::MsMs 2237071 Specdb::MsMs 2238460 Specdb::MsMs 2239098 Specdb::MsMs 2240588 Specdb::MsMs 2241130 Specdb::MsMs 2242621 Specdb::MsMs 2243211 Specdb::MsMs 2248801 5462244 4575341 C02713 21615 Kanehisa, 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. 22080510 van 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. 17765195 Suvorov, 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. 18700763 Mizyed, 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. 15751977 Schwartz, 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. 12369847 Raymond, 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. 14659546 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml N-acetylmuramoyl-L-alanine amidase AmiB P26365 AMIB_ECOLI amiB http://ecmdb.ca/proteins/P26365.xml Probable N-acetylmuramoyl-L-alanine amidase AmiA P36548 AMIA_ECOLI amiA http://ecmdb.ca/proteins/P36548.xml N-acetylmuramoyl-L-alanine amidase AmiC P63883 AMIC_ECOLI amiC http://ecmdb.ca/proteins/P63883.xml Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml PTS system N-acetylmuramic acid-specific EIIBC component P77272 PTYBC_ECOLI murP http://ecmdb.ca/proteins/P77272.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml PTS system N-acetylmuramic acid-specific EIIBC component P77272 PTYBC_ECOLI murP http://ecmdb.ca/proteins/P77272.xml Sugar efflux transporter C P31436 SETC_ECOLI setC http://ecmdb.ca/proteins/P31436.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Phosphoenolpyruvic acid + N-Acetyl-D-muramoate > N-Acetylmuramic acid 6-phosphate + Pyruvic acid N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine R04112 N-Acetyl-D-muramoate + Protein N(pi)-phospho-L-histidine <> N-Acetylmuramic acid 6-phosphate + Protein histidine R08559 N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine