2.0 2012-05-31 13:58:14 -0600 2015-09-17 15:41:46 -0600 ECMDB03266 M2MDB000485 UDP-N-Acetylmuraminate UDP-N-acetylmuaminate is nucleoside diphosphate sugar which is formed from UDP-N-acetylglucosamine and phosphoenolpyruvate. It is a key component of peptidoglycan synthesis. 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-Acetylmuramoyl-UDP UDP-N-acetyl-D-muramate UDP-N-acetylmuramic acid UDP-N-acetylmuramoyl UDP-MurNaAcA UDP-MurNAc UDP-N-Acetyl-D-muramate UDP-N-Acetyl-D-muramic acid UDP-N-Acetylmuramate UDP-N-Acetylmuramic acid UDP-N-Acetylmuraminic acid UDP-N-Acetylmuramoyl Uridine diphosphate N-acetylmuramic acid Uridine diphosphate N-acetylmuramate Uridine diphosphate N-acetylmuramic acid Uridine diphosphoric acid n-acetylmuramic acid Uridine diphosphoric acid N-acetylmuramic acid C20H31N3O19P2 679.4164 679.102698849 (2R)-2-{[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid (2R)-2-{[(3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid CC(OC1C(O)C(CO)OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=CC(=O)NC2=O)C1NC(C)=O)C(O)=O InChI=1S/C20H31N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,7,9-10,12-17,19,24,27-29H,5-6H2,1-2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32) NQBRVZNDBBMBLJ-UHFFFAOYSA-N Solid Cytosol logp -1.58 ALOGPS logs -1.65 ALOGPS solubility 1.53e+01 g/l ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (2R)-2-{[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid ChemAxon average_mass 679.4164 ChemAxon mono_mass 679.102698849 ChemAxon smiles CC(OC1C(O)C(CO)OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=CC(=O)NC2=O)C1NC(C)=O)C(O)=O ChemAxon formula C20H31N3O19P2 ChemAxon inchi InChI=1S/C20H31N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,7,9-10,12-17,19,24,27-29H,5-6H2,1-2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32) ChemAxon inchikey NQBRVZNDBBMBLJ-UHFFFAOYSA-N ChemAxon polar_surface_area 333.69 ChemAxon refractivity 133.73 ChemAxon polarizability 57.36 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 18 ChemAxon donor_count 9 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Amino sugar and nucleotide sugar metabolism ec00520 Peptidoglycan biosynthesis ec00550 D-Glutamine and D-glutamate metabolism L-glutamine is transported into the cytoplasm through a glutamine ABC transporter. Once inside, L-glutamine is metabolized with glutaminase to produce an L-glutamic acid. This process can be reversed through a glutamine synthetase resulting in L-glutamine. L-glutamic acid can also be transported into the cytoplasm through various methods: a glutamate/aspartate:H+ symporter GltP, a glutamate: sodium symporter or a glutamate/aspartate ABC transporter. L-glutamic acid can proceed to L-glutamate metabolism or it can undergo a reversible reaction through a glutamate racemase resulting in D-glutamic acid. This compound can also be obtained from D-glutamine interacting with a glutaminase. D-glutamic acid reacts with UDP-N-acetylmuramoyl-L-alanine through an ATP driven UDP-N-acetylmuramoylalanine-D-glutamate ligase resulting in a UDP-N-acetylmuramoyl-L-alanyl-D-glutamate which is then integrated into the peptidoglycan biosynthesis UDP-N-acetylmuramoyl-L-alanine comes from the amino sugar and nucleotide sugar metabolism product, UDP-N-acetylmuraminate which reacts with L-alanine through an ATP-driven UDP-N-acetylmuramate-L-alanine ligase. PW000769 ec00471 Metabolic Metabolic pathways eco01100 UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-DAP-containing) PWY-6387 Specdb::MsMs 26354 Specdb::MsMs 26355 Specdb::MsMs 26356 Specdb::MsMs 32912 Specdb::MsMs 32913 Specdb::MsMs 32914 HMDB11720 1169 1136 C01050 17882 UDP-N-ACETYLMURAMATE Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 UDP-N-acetylenolpyruvoylglucosamine reductase P08373 MURB_ECOLI murB http://ecmdb.ca/proteins/P08373.xml UDP-N-acetylmuramate--L-alanine ligase P17952 MURC_ECOLI murC http://ecmdb.ca/proteins/P17952.xml UDP-N-acetylmuramate:L-alanyl-gamma-D-glutamyl-meso-diaminopimelate ligase P37773 MPL_ECOLI mpl http://ecmdb.ca/proteins/P37773.xml L-Alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanine R03193 UDP-NACMUR-ALA-LIG-RXN Hydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine <> NADP + UDP-N-Acetylmuraminate R03192 UDPNACETYLMURAMATEDEHYDROG-RXN L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate > ADP + Hydrogen ion + Phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate-D-alanine L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + Adenosine triphosphate + UDP-N-Acetylmuraminate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate UDP-N-Acetylmuraminate + NAD <> UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADH + Hydrogen ion R03191 UDP-N-Acetylmuraminate + NADP <> UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADPH + Hydrogen ion R03192 Adenosine triphosphate + UDP-N-Acetylmuraminate + L-Alanine <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanine R03193 UDP-N-Acetylmuraminate + L-Ala-D-Glu-meso-A2pm + Adenosine triphosphate > Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + ADP + Phosphate RXN0-2361 NADP + UDP-N-Acetylmuraminate < Hydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine UDPNACETYLMURAMATEDEHYDROG-RXN UDP-N-Acetylmuraminate + NADP > UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADPH Adenosine triphosphate + UDP-N-Acetylmuraminate + L-Alanine > ADP + Inorganic phosphate + UDP-N-Acetylmuramoyl-L-alanine UDP-N-acetylmuraminate + Adenosine triphosphate + L-Alanine + UDP-N-Acetylmuraminate + L-Alanine > UDP-N-Acetylmuramoyl-L-alanine + Adenosine diphosphate + Phosphate + ADP PW_R002517 Hydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine <> NADP + UDP-N-Acetylmuraminate UDP-N-Acetylmuraminate + NAD <> UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADH + Hydrogen ion L-Alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanine Hydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine <> NADP + UDP-N-Acetylmuraminate L-Alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanine