2.02012-05-31 14:31:35 -06002015-06-03 17:19:28 -0600ECMDB20177M2MDB001024N-Acetylmuramic acid 6-phosphateN-acetylmuramic acid 6-phosphate 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. The enzyme MurQ is an N-acetylmuramic acid 6-phosphate (MurNAc 6-phosphate) hydrolase (or etherase) that hydrolyzes the lactyl side chain from MurNAc 6-phosphate and generates GlcNAc 6-phosphate. (PMID 18837509). 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.MurNAc 6-phosphateMurNAc 6-phosphoric acidMurNAc-6-PN-Acetylmuramate 6-phosphateN-Acetylmuramic acid 6-phosphoric acidC11H20NO11P373.2504373.077396999(2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(phosphonooxy)methyl]oxan-4-yl]oxy}propanoic acidMurNAc 6-phosphate[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(COP(O)(O)=O)OC([H])(O)[C@]1([H])N=C(C)O)C(O)=OInChI=1S/C11H20NO11P/c1-4(10(15)16)22-9-7(12-5(2)13)11(17)23-6(8(9)14)3-21-24(18,19)20/h4,6-9,11,14,17H,3H2,1-2H3,(H,12,13)(H,15,16)(H2,18,19,20)/t4-,6-,7-,8-,9-,11?/m1/s1NMEMTQKUEVNSPV-MKFCKLDKSA-NCytosollogp-1.84logs-1.22solubility2.24e+01 g/llogp-2.5pka_strongest_acidic0.97pka_strongest_basic1.58iupac(2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(phosphonooxy)methyl]oxan-4-yl]oxy}propanoic acidaverage_mass373.2504mono_mass373.077396999smiles[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(COP(O)(O)=O)OC([H])(O)[C@]1([H])N=C(C)O)C(O)=OformulaC11H20NO11PinchiInChI=1S/C11H20NO11P/c1-4(10(15)16)22-9-7(12-5(2)13)11(17)23-6(8(9)14)3-21-24(18,19)20/h4,6-9,11,14,17H,3H2,1-2H3,(H,12,13)(H,15,16)(H2,18,19,20)/t4-,6-,7-,8-,9-,11?/m1/s1inchikeyNMEMTQKUEVNSPV-MKFCKLDKSA-Npolar_surface_area195.57refractivity73.75polarizability32.01rotatable_bond_count7acceptor_count11donor_count6physiological_charge-3formal_charge0Amino sugar and nucleotide sugar metabolismec00520Phosphotransferase system (PTS)ec020601,6-anhydro-<i>N</i>-acetylmuramic acid recyclingPWY0-1261Specdb::CMs1083513Specdb::EiMs5029Specdb::NmrOneD336138Specdb::NmrOneD336139Specdb::NmrOneD336140Specdb::NmrOneD336141Specdb::NmrOneD336142Specdb::NmrOneD336143Specdb::NmrOneD336144Specdb::NmrOneD336145Specdb::NmrOneD336146Specdb::NmrOneD336147Specdb::NmrOneD336148Specdb::NmrOneD336149Specdb::NmrOneD336150Specdb::NmrOneD336151Specdb::NmrOneD336152Specdb::NmrOneD336153Specdb::NmrOneD336154Specdb::NmrOneD336155Specdb::NmrOneD336156Specdb::NmrOneD336157Specdb::MsMs25913Specdb::MsMs25914Specdb::MsMs25915Specdb::MsMs32471Specdb::MsMs32472Specdb::MsMs324732479872021865486C1669847968CPD0-881Keseler, 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-D114.22080510Phosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlGlucose-specific phosphotransferase enzyme IIA componentP69783PTGA_ECOLIcrrhttp://ecmdb.ca/proteins/P69783.xmlN-acetylmuramic acid 6-phosphate etheraseP76535MURQ_ECOLImurQhttp://ecmdb.ca/proteins/P76535.xmlPTS system N-acetylmuramic acid-specific EIIBC componentP77272PTYBC_ECOLImurPhttp://ecmdb.ca/proteins/P77272.xmlAnhydro-N-acetylmuramic acid kinaseP77570ANMK_ECOLIanmKhttp://ecmdb.ca/proteins/P77570.xmlPhosphocarrier protein HPrP0AA04PTHP_ECOLIptsHhttp://ecmdb.ca/proteins/P0AA04.xmlPTS system N-acetylmuramic acid-specific EIIBC componentP77272PTYBC_ECOLImurPhttp://ecmdb.ca/proteins/P77272.xmlPhosphoenolpyruvic acid + N-Acetyl-D-muramoate > N-Acetylmuramic acid 6-phosphate + Pyruvic acid1,6-Anhydro-N-acetylmuramate + Adenosine triphosphate + Water > N-Acetylmuramic acid 6-phosphate + ADP + Hydrogen ionRXN0-4621N-Acetylmuramic acid 6-phosphate + Water <> N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acidR08555RXN0-4641N-Acetyl-D-muramoate + Protein N(pi)-phospho-L-histidine <> N-Acetylmuramic acid 6-phosphate + Protein histidineR08559Phosphoenolpyruvic acid + <i>N</i>-acetylmuramate > N-Acetylmuramic acid 6-phosphate + Pyruvic acidRXN0-17Adenosine triphosphate + 1,6-Anhydro-N-acetyl-beta-muramate + Water > ADP + N-Acetylmuramic acid 6-phosphateN-Acetylmuramic acid 6-phosphate + Water > N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acidAdenosine triphosphate + 1,6-Anhydro-N-acetyl-beta-muramate + Water <> ADP + N-Acetylmuramic acid 6-phosphateR09640