2.02012-05-31 14:53:23 -06002015-06-03 17:20:23 -0600ECMDB20612M2MDB001411dTDP-D-FucosaminedTDP-D-fucosamine 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. This compound is involved in the synthesis of enterobacterial common antigen (ECA) synthesis through the reaction: dTDP-alpha-D-fucosamine + acetyl-CoA <=> dTDP-4-acetamido-4,6-dideoxy-D-galactose + coenzyme A + H+. Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae (including E. coli). The carbohydrate portion of this glycolipid consists of N-acetyl-glucosamine, N-acetyl-D-mannosaminuronic acid and 4-acetamido-4,6-dideoxy-D-galactose. These amino sugars form trisaccharide repeat units which are part of linear heteropolysaccharide chains.DTDP-4-amino-4,6-dideoxy-α-D-galactosedTDP-4-amino-4,6-Dideoxy-a-D-galactoseDTDP-4-Amino-4,6-dideoxy-alpha-D-galactoseDTDP-4-Amino-4,6-dideoxy-D-galactosedTDP-4-amino-4,6-Dideoxy-α-D-galactoseTDP-D-FucosamineTDP-FucnTDP-FucosamineC16H27N3O14P2547.3448547.096825611[({[(2R,3R,4S,5R,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid{[(2R,3R,4S,5R,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy(hydroxy)phosphoryl}oxy[3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxyphosphinic acid[H]C1(O)CC([H])(OC1([H])COP(O)(=O)OP(O)(=O)O[C@@]1([H])O[C@]([H])(C)[C@]([H])(N)[C@]([H])(O)[C@@]1([H])O)N1C=C(C)C(O)=NC1=OInChI=1S/C16H27N3O14P2/c1-6-4-19(16(24)18-14(6)23)10-3-8(20)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(17)7(2)30-15/h4,7-13,15,20-22H,3,5,17H2,1-2H3,(H,25,26)(H,27,28)(H,18,23,24)/t7-,8?,9?,10?,11+,12+,13-,15-/m1/s1UIVJXHWSIFBBCY-DBRXDORISA-NCytosollogp-1.65logs-1.58solubility1.43e+01 g/llogp-3.6pka_strongest_acidic1.73pka_strongest_basic8.9iupac[({[(2R,3R,4S,5R,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acidaverage_mass547.3448mono_mass547.096825611smiles[H]C1(O)CC([H])(OC1([H])COP(O)(=O)OP(O)(=O)O[C@@]1([H])O[C@]([H])(C)[C@]([H])(N)[C@]([H])(O)[C@@]1([H])O)N1C=C(C)C(O)=NC1=OformulaC16H27N3O14P2inchiInChI=1S/C16H27N3O14P2/c1-6-4-19(16(24)18-14(6)23)10-3-8(20)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(17)7(2)30-15/h4,7-13,15,20-22H,3,5,17H2,1-2H3,(H,25,26)(H,27,28)(H,18,23,24)/t7-,8?,9?,10?,11+,12+,13-,15-/m1/s1inchikeyUIVJXHWSIFBBCY-DBRXDORISA-Npolar_surface_area260.36refractivity109.74polarizability46.89rotatable_bond_count8acceptor_count13donor_count7physiological_charge-1formal_charge0Secondary Metabolites: enterobacterial common antigen biosynthesis 3The biosynthesis of a enterobacterial common antigen can begin with a di-trans,octa-cis-undecaprenyl phosphate interacts with a Uridine diphosphate-N-acetylglucosamine through undecaprenyl-phosphate α-N-acetylglucosaminyl transferase resulting in a N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol and a Uridine 5'-monophosphate. The N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol then reacts with an UDP-ManNAcA from the Amino sugar and nucleotide sugar metabolism pathway. This reaction is metabolized by a UDP-N-acetyl-D-mannosaminuronic acid transferase resulting in a uridine 5' diphosphate, a hydrogen ion and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. Glucose 1 phosphate can be metabolize by interacting with a hydrogen ion and a thymidine 5-triphosphate by either reacting with a dTDP-glucose pyrophosphorylase or a dTDP-glucose pyrophosphorylase 2 resulting in the release of a pyrophosphate and a dTDP-D-glucose. The latter compound is then dehydrated through an dTDP-glucose 4,6-dehydratase 2 resulting in water and dTDP-4-dehydro-6-deoxy-D-glucose. The latter compound interacts with L-glutamic acid through a dTDP-4-dehydro-6-deoxy-D-glucose transaminase resulting in the release of oxoglutaric acid and dTDP-thomosamine. The latter compound interacts with acetyl-coa through a dTDP-fucosamine acetyltransferase resulting in a Coenzyme A, a hydrogen Ion and a TDP-Fuc4NAc. Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate then interacts with a TDP--Fuc4NAc through a 4-acetamido-4,6-dideoxy-D-galactose transferase resulting in a hydrogen ion, a dTDP and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. This compound is then transported through a protein wzxE into the periplasmic space so that it can be incorporated into the outer membrane Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae. ECA is a unique cell surface antigen that can be found in the outer leaflet of the outer membrane. The carbohydrate portion consists of N-acetyl-glucosamine, N-acetyl-D-mannosaminuronic acid and 4-acetamido-4,6-dideoxy-D-galactose. These amino sugars form trisaccharide repeat units which are part of linear heteropolysaccharide chains.PW002046Metabolicenterobacterial common antigen biosynthesisECASYN-PWYSpecdb::CMs1083636Specdb::NmrOneD288555Specdb::NmrOneD288556Specdb::NmrOneD288557Specdb::NmrOneD288558Specdb::NmrOneD288559Specdb::NmrOneD288560Specdb::NmrOneD288561Specdb::NmrOneD288562Specdb::NmrOneD288563Specdb::NmrOneD288564Specdb::NmrOneD288565Specdb::NmrOneD288566Specdb::NmrOneD288567Specdb::NmrOneD288568Specdb::NmrOneD288569Specdb::NmrOneD288570Specdb::NmrOneD288571Specdb::NmrOneD288572Specdb::NmrOneD288573Specdb::NmrOneD288574Specdb::MsMs24833Specdb::MsMs24834Specdb::MsMs24835Specdb::MsMs31391Specdb::MsMs31392Specdb::MsMs3139325202013C04346TDP-D-FUCOSAMINEKeseler, 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 80:2939-2948.18331064Lipopolysaccharide biosynthesis protein rffCP27832RFFC_ECOLIrffChttp://ecmdb.ca/proteins/P27832.xmlLipopolysaccharide biosynthesis protein rffAP27833RFFA_ECOLIrffAhttp://ecmdb.ca/proteins/P27833.xmlAcetyl-CoA + dTDP-D-Fucosamine > Coenzyme A + dTDP-4-Acetamido-4,6-dideoxy-D-galactose + Hydrogen ionTDPFUCACTRANS-RXN4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate > alpha-Ketoglutarate + dTDP-D-Fucosamine4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate <> dTDP-D-Fucosamine + Oxoglutaric acidRFFTRANS-RXNAcetyl-CoA + dTDP-D-Fucosamine <> Coenzyme A + dTDP-4-acetamido-4,6-dideoxy-alpha-D-galactoseR10142 dTDP-D-Fucosamine + alpha-Ketoglutarate <> 4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-GlutamateR04438 dTDP-4-dehydro-6-deoxy-D-glucose + L-Glutamate > Oxoglutaric acid + dTDP-D-FucosaminePW_R005969