2.0 2012-05-31 14:53:23 -0600 2015-06-03 17:20:23 -0600 ECMDB20612 M2MDB001411 dTDP-D-Fucosamine dTDP-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-&alpha;-D-galactose dTDP-4-amino-4,6-Dideoxy-a-D-galactose DTDP-4-Amino-4,6-dideoxy-alpha-D-galactose DTDP-4-Amino-4,6-dideoxy-D-galactose dTDP-4-amino-4,6-Dideoxy-α-D-galactose TDP-D-Fucosamine TDP-Fucn TDP-Fucosamine C16H27N3O14P2 547.3448 547.096825611 [({[(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=O InChI=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/s1 UIVJXHWSIFBBCY-DBRXDORISA-N Cytosol logp -1.65 ALOGPS logs -1.58 ALOGPS solubility 1.43e+01 g/l ALOGPS logp -3.6 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic 8.9 ChemAxon iupac [({[(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 ChemAxon average_mass 547.3448 ChemAxon mono_mass 547.096825611 ChemAxon smiles [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=O ChemAxon formula C16H27N3O14P2 ChemAxon inchi InChI=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/s1 ChemAxon inchikey UIVJXHWSIFBBCY-DBRXDORISA-N ChemAxon polar_surface_area 260.36 ChemAxon refractivity 109.74 ChemAxon polarizability 46.89 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 13 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Secondary Metabolites: enterobacterial common antigen biosynthesis 3 The 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. PW002046 Metabolic enterobacterial common antigen biosynthesis ECASYN-PWY Specdb::CMs 1083636 Specdb::NmrOneD 288555 Specdb::NmrOneD 288556 Specdb::NmrOneD 288557 Specdb::NmrOneD 288558 Specdb::NmrOneD 288559 Specdb::NmrOneD 288560 Specdb::NmrOneD 288561 Specdb::NmrOneD 288562 Specdb::NmrOneD 288563 Specdb::NmrOneD 288564 Specdb::NmrOneD 288565 Specdb::NmrOneD 288566 Specdb::NmrOneD 288567 Specdb::NmrOneD 288568 Specdb::NmrOneD 288569 Specdb::NmrOneD 288570 Specdb::NmrOneD 288571 Specdb::NmrOneD 288572 Specdb::NmrOneD 288573 Specdb::NmrOneD 288574 Specdb::MsMs 24833 Specdb::MsMs 24834 Specdb::MsMs 24835 Specdb::MsMs 31391 Specdb::MsMs 31392 Specdb::MsMs 31393 25202013 C04346 TDP-D-FUCOSAMINE 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 van 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. 17765195 Winder, 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. 18331064 Lipopolysaccharide biosynthesis protein rffC P27832 RFFC_ECOLI rffC http://ecmdb.ca/proteins/P27832.xml Lipopolysaccharide biosynthesis protein rffA P27833 RFFA_ECOLI rffA http://ecmdb.ca/proteins/P27833.xml Acetyl-CoA + dTDP-D-Fucosamine > Coenzyme A + dTDP-4-Acetamido-4,6-dideoxy-D-galactose + Hydrogen ion TDPFUCACTRANS-RXN 4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate > alpha-Ketoglutarate + dTDP-D-Fucosamine 4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate <> dTDP-D-Fucosamine + Oxoglutaric acid RFFTRANS-RXN Acetyl-CoA + dTDP-D-Fucosamine <> Coenzyme A + dTDP-4-acetamido-4,6-dideoxy-alpha-D-galactose R10142 dTDP-D-Fucosamine + alpha-Ketoglutarate <> 4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate R04438 dTDP-4-dehydro-6-deoxy-D-glucose + L-Glutamate > Oxoglutaric acid + dTDP-D-Fucosamine PW_R005969