2.0 2015-09-08 17:50:20 -0600 2015-09-14 16:46:42 -0600 ECMDB24236 M2MDB006353 UDP-N-acetyl-α-D-mannosaminuronate UDP-N-acetyl-alpha-D-mannosaminuronate is an intermediate in several pathways in E.coli. In enterobacterial common antigen biosynthesis, it is a substrate for the enzyme UDP-N-acetyl-D-mannosaminuronic acid transferase which catalyzes the reaction N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol + UDP-N-acetyl-alpha-D-mannosaminuronate -> N-acetyl-β-D-mannosaminuronyl-(1→4)-N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol + UDP + H+. It is also a product for enzyme UDP-N-acetyl-D-mannosamine dehydrogenase which catalyzes reaction UDP-N-acetyl-alpha-D-mannosamine + 2 NAD+ + H2O -> UDP-N-acetyl-alpha-D-mannosaminuronate + 2 NADH + 3 H+ in UDP-N-acetyl-α-D-mannosaminouronate biosynthesis pathway (BioCyc compound: UDP-MANNACA). UDP-N-Acetyl-α-D-mannosaminuronic acid C17H22N3O18P2 618.315 618.039005616 6-{[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}-5-acetamido-3,4-dihydroxyoxane-2-carboxylate 6-[({[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphinato)oxy]-5-acetamido-3,4-dihydroxyoxane-2-carboxylate CC(=O)NC1C(O)C(O)C(OC1OP([O-])(=O)OP([O-])(=O)OCC1OC(C(O)C1O)N1C=CC(=O)NC1=O)C([O-])=O InChI=1S/C17H25N3O18P2/c1-5(21)18-8-10(24)11(25)13(15(27)28)36-16(8)37-40(32,33)38-39(30,31)34-4-6-9(23)12(26)14(35-6)20-3-2-7(22)19-17(20)29/h2-3,6,8-14,16,23-26H,4H2,1H3,(H,18,21)(H,27,28)(H,30,31)(H,32,33)(H,19,22,29)/p-3 DZOGQXKQLXAPND-UHFFFAOYSA-K logp -1.17 ALOGPS logs -1.38 ALOGPS solubility 2.81e+01 g/l ALOGPS logp -5 ChemAxon pka_strongest_acidic 1.72 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac 6-{[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}-5-acetamido-3,4-dihydroxyoxane-2-carboxylate ChemAxon average_mass 618.315 ChemAxon mono_mass 618.039005616 ChemAxon smiles CC(=O)NC1C(O)C(O)C(OC1OP([O-])(=O)OP([O-])(=O)OCC1OC(C(O)C1O)N1C=CC(=O)NC1=O)C([O-])=O ChemAxon formula C17H22N3O18P2 ChemAxon inchi InChI=1S/C17H25N3O18P2/c1-5(21)18-8-10(24)11(25)13(15(27)28)36-16(8)37-40(32,33)38-39(30,31)34-4-6-9(23)12(26)14(35-6)20-3-2-7(22)19-17(20)29/h2-3,6,8-14,16,23-26H,4H2,1H3,(H,18,21)(H,27,28)(H,30,31)(H,32,33)(H,19,22,29)/p-3 ChemAxon inchikey DZOGQXKQLXAPND-UHFFFAOYSA-K ChemAxon polar_surface_area 325.97 ChemAxon refractivity 126.02 ChemAxon polarizability 50.41 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 15 ChemAxon donor_count 6 ChemAxon physiological_charge -3 ChemAxon formal_charge -3 ChemAxon Amino sugar and nucleotide sugar metabolism I The synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate. N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound can either be isomerized or deaminated into Beta-D-fructofuranose 6-phosphate through a glucosamine-fructose-6-phosphate aminotransferase and a glucosamine-6-phosphate deaminase respectively. Glucosamine 6-phosphate undergoes a reversible reaction to glucosamine 1 phosphate through a phosphoglucosamine mutase. This compound is then acetylated through a bifunctional protein glmU to produce a N-Acetyl glucosamine 1-phosphate. N-Acetyl glucosamine 1-phosphate enters the nucleotide sugar synthesis by reacting with UTP and hydrogen ion through a bifunctional protein glmU releasing pyrophosphate and a Uridine diphosphate-N-acetylglucosamine.This compound can either be isomerized into a UDP-N-acetyl-D-mannosamine or undergo a reaction with phosphoenolpyruvic acid through UDP-N-acetylglucosamine 1-carboxyvinyltransferase releasing a phosphate and a UDP-N-Acetyl-alpha-D-glucosamine-enolpyruvate. UDP-N-acetyl-D-mannosamine undergoes a NAD dependent dehydrogenation through a UDP-N-acetyl-D-mannosamine dehydrogenase, releasing NADH, a hydrogen ion and a UDP-N-Acetyl-alpha-D-mannosaminuronate, This compound is then used in the production of enterobacterial common antigens. UDP-N-Acetyl-alpha-D-glucosamine-enolpyruvate is reduced through a NADPH dependent UDP-N-acetylenolpyruvoylglucosamine reductase, releasing a NADP and a UDP-N-acetyl-alpha-D-muramate. This compound is involved in the D-glutamine and D-glutamate metabolism. PW000886 Metabolic Specdb::NmrOneD 253228 Specdb::NmrOneD 253229 Specdb::NmrOneD 253230 Specdb::NmrOneD 253231 Specdb::NmrOneD 253232 Specdb::NmrOneD 253233 Specdb::NmrOneD 253234 Specdb::NmrOneD 253235 Specdb::NmrOneD 253236 Specdb::NmrOneD 253237 Specdb::NmrOneD 253238 Specdb::NmrOneD 253239 Specdb::NmrOneD 253240 Specdb::NmrOneD 253241 Specdb::NmrOneD 253242 Specdb::NmrOneD 253243 Specdb::NmrOneD 253244 Specdb::NmrOneD 253245 Specdb::NmrOneD 253246 Specdb::NmrOneD 253247 Specdb::MsMs 23267 Specdb::MsMs 23268 Specdb::MsMs 23269 Specdb::MsMs 30065 Specdb::MsMs 30066 Specdb::MsMs 30067 UDP-N-acetyl-D-mannosamine dehydrogenase P27829 WECC_ECOLI wecC http://ecmdb.ca/proteins/P27829.xml UDP-N-acetyl-D-mannosamine + 2 NAD + Water + UDP-N-Acetyl-D-mannosamine > UDP-N-acetyl-α-D-mannosaminuronate +2 NADH +3 Hydrogen ion PW_R003316