2.0 2012-05-31 14:31:35 -0600 2015-06-03 17:19:28 -0600 ECMDB20177 M2MDB001024 N-Acetylmuramic acid 6-phosphate N-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-phosphate MurNAc 6-phosphoric acid MurNAc-6-P N-Acetylmuramate 6-phosphate N-Acetylmuramic acid 6-phosphoric acid C11H20NO11P 373.2504 373.077396999 (2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(phosphonooxy)methyl]oxan-4-yl]oxy}propanoic acid MurNAc 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)=O InChI=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/s1 NMEMTQKUEVNSPV-MKFCKLDKSA-N Cytosol logp -1.84 ALOGPS logs -1.22 ALOGPS solubility 2.24e+01 g/l ALOGPS logp -2.5 ChemAxon pka_strongest_acidic 0.97 ChemAxon pka_strongest_basic 1.58 ChemAxon iupac (2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(phosphonooxy)methyl]oxan-4-yl]oxy}propanoic acid ChemAxon average_mass 373.2504 ChemAxon mono_mass 373.077396999 ChemAxon smiles [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)=O ChemAxon formula C11H20NO11P ChemAxon inchi InChI=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/s1 ChemAxon inchikey NMEMTQKUEVNSPV-MKFCKLDKSA-N ChemAxon polar_surface_area 195.57 ChemAxon refractivity 73.75 ChemAxon polarizability 32.01 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 11 ChemAxon donor_count 6 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Amino sugar and nucleotide sugar metabolism ec00520 Phosphotransferase system (PTS) ec02060 1,6-anhydro-<i>N</i>-acetylmuramic acid recycling PWY0-1261 Specdb::CMs 1083513 Specdb::EiMs 5029 Specdb::NmrOneD 336138 Specdb::NmrOneD 336139 Specdb::NmrOneD 336140 Specdb::NmrOneD 336141 Specdb::NmrOneD 336142 Specdb::NmrOneD 336143 Specdb::NmrOneD 336144 Specdb::NmrOneD 336145 Specdb::NmrOneD 336146 Specdb::NmrOneD 336147 Specdb::NmrOneD 336148 Specdb::NmrOneD 336149 Specdb::NmrOneD 336150 Specdb::NmrOneD 336151 Specdb::NmrOneD 336152 Specdb::NmrOneD 336153 Specdb::NmrOneD 336154 Specdb::NmrOneD 336155 Specdb::NmrOneD 336156 Specdb::NmrOneD 336157 Specdb::MsMs 25913 Specdb::MsMs 25914 Specdb::MsMs 25915 Specdb::MsMs 32471 Specdb::MsMs 32472 Specdb::MsMs 32473 24798720 21865486 C16698 47968 CPD0-881 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 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml N-acetylmuramic acid 6-phosphate etherase P76535 MURQ_ECOLI murQ http://ecmdb.ca/proteins/P76535.xml PTS system N-acetylmuramic acid-specific EIIBC component P77272 PTYBC_ECOLI murP http://ecmdb.ca/proteins/P77272.xml Anhydro-N-acetylmuramic acid kinase P77570 ANMK_ECOLI anmK http://ecmdb.ca/proteins/P77570.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 Phosphoenolpyruvic acid + N-Acetyl-D-muramoate > N-Acetylmuramic acid 6-phosphate + Pyruvic acid 1,6-Anhydro-N-acetylmuramate + Adenosine triphosphate + Water > N-Acetylmuramic acid 6-phosphate + ADP + Hydrogen ion RXN0-4621 N-Acetylmuramic acid 6-phosphate + Water <> N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid R08555 RXN0-4641 N-Acetyl-D-muramoate + Protein N(pi)-phospho-L-histidine <> N-Acetylmuramic acid 6-phosphate + Protein histidine R08559 Phosphoenolpyruvic acid + <i>N</i>-acetylmuramate > N-Acetylmuramic acid 6-phosphate + Pyruvic acid RXN0-17 Adenosine triphosphate + 1,6-Anhydro-N-acetyl-beta-muramate + Water > ADP + N-Acetylmuramic acid 6-phosphate N-Acetylmuramic acid 6-phosphate + Water > N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid Adenosine triphosphate + 1,6-Anhydro-N-acetyl-beta-muramate + Water <> ADP + N-Acetylmuramic acid 6-phosphate R09640