2.02012-05-31 14:32:54 -06002015-09-17 15:41:49 -0600ECMDB20202M2MDB001048UDP-N-Acetyl-D-mannosamineUDP-N-acetyl-D-mannosamine is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. UDP-AcetylmannosamineUDP-ManNAcUridine 5'-(trihydrogen diphosphate), P'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) esterUridine 5'-(trihydrogen diphosphate), p'-(2-(acetylamino)-2-deoxy-a-D-mannopyranosyl) esterUridine 5'-(trihydrogen diphosphate), P'-(2-(acetylamino)-2-deoxy-alpha-D-mannopyranosyl) esterUridine 5'-(trihydrogen diphosphate), p'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) esterUridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) esterUridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-a-D-mannopyranosyl) esterUridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-alpha-D-mannopyranosyl) esterUridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) esterUridine diphosphate <i>N</i>-acetylmannosamineUridine diphosphate N-acetylgalactosamineUridine diphosphate N-acetylmannosamineUridine diphosphoric acid N-acetylgalactosamineUridine diphosphoric acid N-acetylmannosamineUridine diphosphoric acid n-acetylmannosamineUridine-diphosphate-n-acetylgalactosamineUridine-diphosphate-n-acetylglucosamineUridine-diphosphoric acid-N-acetylgalactosamineUridine-diphosphoric acid-N-acetylglucosamineC17H27N3O17P2607.3537607.081569477N-[(3S,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)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acidN-[(3S,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]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid26575-17-7CC(=O)N[C@@H]1[C@H](O)[C@@H](O)[C@H](CO)OC1OP(O)(=O)OP(O)(=O)OC[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)N1C=CC(=O)NC1=OInChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10+,11-,12-,13-,14-,15-,16?/m0/s1LFTYTUAZOPRMMI-IUPDHGCPSA-NCytosollogp-1.70logs-1.67solubility1.30e+01 g/llogp-4.1pka_strongest_acidic1.73pka_strongest_basic-3.6iupacN-[(3S,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)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acidaverage_mass607.3537mono_mass607.081569477smilesCC(=O)N[C@@H]1[C@H](O)[C@@H](O)[C@H](CO)OC1OP(O)(=O)OP(O)(=O)OC[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)N1C=CC(=O)NC1=OformulaC17H27N3O17P2inchiInChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10+,11-,12-,13-,14-,15-,16?/m0/s1inchikeyLFTYTUAZOPRMMI-IUPDHGCPSA-Npolar_surface_area307.39refractivity118.4polarizability50.85rotatable_bond_count10acceptor_count16donor_count9physiological_charge-1formal_charge0Amino sugar and nucleotide sugar metabolismec00520Metabolic pathwayseco01100Amino sugar and nucleotide sugar metabolism IThe 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.
PW000886Metabolicenterobacterial common antigen biosynthesisECASYN-PWYSpecdb::MsMs27473Specdb::MsMs27474Specdb::MsMs27475Specdb::MsMs34031Specdb::MsMs34032Specdb::MsMs34033HMDB13112449043395672C0117016287UDP-MANNACKeseler, 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-acetylglucosamine 2-epimeraseP27828WECB_ECOLIwecBhttp://ecmdb.ca/proteins/P27828.xmlUDP-N-acetyl-D-mannosamine dehydrogenaseP27829WECC_ECOLIwecChttp://ecmdb.ca/proteins/P27829.xmlUridine diphosphate-N-acetylglucosamine <> UDP-N-Acetyl-D-mannosamineR00420UDPGLCNACEPIM-RXNWater + 2 NAD + UDP-N-Acetyl-D-mannosamine <>3 Hydrogen ion +2 NADH + UDP-N-Acetyl-D-mannosaminouronateR03317UDPMANNACADEHYDROG-RXNUDP-N-Acetyl-D-mannosamine + 2 NAD + Water <> UDP-N-Acetyl-D-mannosaminouronate +2 NADH +2 Hydrogen ionR03317UDP-N-Acetyl-D-mannosamine + NAD + Water <> UDP-N-Acetyl-D-mannosaminouronate + NADH + Hydrogen ionUDPMANNACADEHYDROG-RXNUridine diphosphate-N-acetylglucosamine > UDP-N-Acetyl-D-mannosamineUDP-N-Acetyl-D-mannosamine + 2 NAD + Water > UDP-N-Acetyl-D-mannosaminouronate +2 NADHUridine diphosphate-N-acetylglucosamine <> UDP-N-acetyl-D-mannosamine + UDP-N-Acetyl-D-mannosaminePW_R003315UDP-N-acetyl-D-mannosamine + 2 NAD + Water + UDP-N-Acetyl-D-mannosamine > UDP-N-acetyl-α-D-mannosaminuronate +2 NADH +3 Hydrogen ionPW_R003316