2.02012-05-31 13:58:14 -06002015-09-17 15:41:46 -0600ECMDB03266M2MDB000485UDP-N-AcetylmuraminateUDP-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-UDPUDP-<i>N</i>-acetyl-D-muramateUDP-<i>N</i>-acetylmuramic acidUDP-<i>N</i>-acetylmuramoylUDP-MurNaAcAUDP-MurNAcUDP-N-Acetyl-D-muramateUDP-N-Acetyl-D-muramic acidUDP-N-AcetylmuramateUDP-N-Acetylmuramic acidUDP-N-Acetylmuraminic acidUDP-N-AcetylmuramoylUridine diphosphate <i>N</i>-acetylmuramic acidUridine diphosphate N-acetylmuramateUridine diphosphate N-acetylmuramic acidUridine diphosphoric acid n-acetylmuramic acidUridine diphosphoric acid N-acetylmuramic acidC20H31N3O19P2679.4164679.102698849(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 acidCC(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)=OInChI=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-NSolidCytosollogp-1.58logs-1.65solubility1.53e+01 g/llogp-3.4pka_strongest_acidic1.73pka_strongest_basic-3.6iupac(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 acidaverage_mass679.4164mono_mass679.102698849smilesCC(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)=OformulaC20H31N3O19P2inchiInChI=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)inchikeyNQBRVZNDBBMBLJ-UHFFFAOYSA-Npolar_surface_area333.69refractivity133.73polarizability57.36rotatable_bond_count13acceptor_count18donor_count9physiological_charge-2formal_charge0Amino sugar and nucleotide sugar metabolismec00520Peptidoglycan biosynthesisec00550D-Glutamine and D-glutamate metabolismL-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.
PW000769ec00471MetabolicMetabolic pathwayseco01100UDP-<i>N</i>-acetylmuramoyl-pentapeptide biosynthesis III (<i>meso</i>-DAP-containing)PWY-6387Specdb::MsMs26354Specdb::MsMs26355Specdb::MsMs26356Specdb::MsMs32912Specdb::MsMs32913Specdb::MsMs32914HMDB1172011691136C0105017882UDP-N-ACETYLMURAMATEKeseler, 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-D590.21097882Kanehisa, 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064UDP-N-acetylenolpyruvoylglucosamine reductaseP08373MURB_ECOLImurBhttp://ecmdb.ca/proteins/P08373.xmlUDP-N-acetylmuramate--L-alanine ligaseP17952MURC_ECOLImurChttp://ecmdb.ca/proteins/P17952.xmlUDP-N-acetylmuramate:L-alanyl-gamma-D-glutamyl-meso-diaminopimelate ligaseP37773MPL_ECOLImplhttp://ecmdb.ca/proteins/P37773.xmlL-Alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanineR03193UDP-NACMUR-ALA-LIG-RXNHydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine <> NADP + UDP-N-AcetylmuraminateR03192UDPNACETYLMURAMATEDEHYDROG-RXNL-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-alanineL-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-diaminoheptanedioateUDP-N-Acetylmuraminate + NAD <> UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADH + Hydrogen ionR03191UDP-N-Acetylmuraminate + NADP <> UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADPH + Hydrogen ionR03192Adenosine triphosphate + UDP-N-Acetylmuraminate + L-Alanine <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanineR03193UDP-N-Acetylmuraminate + L-Ala-D-Glu-meso-A2pm + Adenosine triphosphate > Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + ADP + PhosphateRXN0-2361NADP + UDP-N-Acetylmuraminate < Hydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamineUDPNACETYLMURAMATEDEHYDROG-RXNUDP-N-Acetylmuraminate + NADP > UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADPHAdenosine triphosphate + UDP-N-Acetylmuraminate + L-Alanine > ADP + Inorganic phosphate + UDP-N-Acetylmuramoyl-L-alanineUDP-N-acetylmuraminate + Adenosine triphosphate + L-Alanine + UDP-N-Acetylmuraminate + L-Alanine > UDP-N-Acetylmuramoyl-L-alanine + Adenosine diphosphate + Phosphate + ADPPW_R002517Hydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine <> NADP + UDP-N-AcetylmuraminateUDP-N-Acetylmuraminate + NAD <> UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADH + Hydrogen ionL-Alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanineHydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine <> NADP + UDP-N-AcetylmuraminateL-Alanine + Adenosine triphosphate + UDP-N-Acetylmuraminate <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanine