2.0 2012-05-31 14:37:52 -0600 2015-06-03 17:19:44 -0600 ECMDB20298 M2MDB001135 TDP-Glucose TDP-glucose 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. Thymidine diphosphate glucose (often abbreviated dTDP-glucose or TDP-glucose) is a nucleotide-linked sugar consisting of deoxythymidine diphosphate linked to glucose. It is the starting compound for the syntheses of many deoxysugars. (WikiPedia) DTDP-D-Glucose DTDP-Glucose TDP-glucose C16H24N2O16P2 562.3131 562.060105754 {[hydroxy({[3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid [hydroxy([3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy([3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid [H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP([O-])(=O)OP(O)(=O)O[C@@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)N1C=C(C)C([O-])=NC1=O InChI=1S/C16H26N2O16P2/c1-6-3-18(16(25)17-14(6)24)10-2-7(20)9(31-10)5-30-35(26,27)34-36(28,29)33-15-13(23)12(22)11(21)8(4-19)32-15/h3,7-13,15,19-23H,2,4-5H2,1H3,(H,26,27)(H,28,29)(H,17,24,25)/p-2/t7-,8+,9+,10+,11+,12-,13+,15+/m0/s1 YSYKRGRSMLTJNL-URARBOGNSA-L Cytoplasm Periplasm logp -1.14 ALOGPS logs -1.52 ALOGPS solubility 1.69e+01 g/l ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3 ChemAxon iupac {[hydroxy({[3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid ChemAxon average_mass 562.3131 ChemAxon mono_mass 562.060105754 ChemAxon smiles [H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP([O-])(=O)OP(O)(=O)O[C@@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)N1C=C(C)C([O-])=NC1=O ChemAxon formula C16H24N2O16P2 ChemAxon inchi InChI=1S/C16H26N2O16P2/c1-6-3-18(16(25)17-14(6)24)10-2-7(20)9(31-10)5-30-35(26,27)34-36(28,29)33-15-13(23)12(22)11(21)8(4-19)32-15/h3,7-13,15,19-23H,2,4-5H2,1H3,(H,26,27)(H,28,29)(H,17,24,25)/p-2/t7-,8+,9+,10+,11+,12-,13+,15+/m0/s1 ChemAxon inchikey YSYKRGRSMLTJNL-URARBOGNSA-L ChemAxon polar_surface_area 274.8 ChemAxon refractivity 109.62 ChemAxon polarizability 47.85 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 14 ChemAxon donor_count 8 ChemAxon physiological_charge -2 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 dTDP-L-rhamnose biosynthesis I DTDPRHAMSYN-PWY Specdb::CMs 282059 Specdb::CMs 351315 Specdb::CMs 351316 Specdb::CMs 351317 Specdb::CMs 351318 Specdb::CMs 351319 Specdb::CMs 351320 Specdb::CMs 351321 Specdb::CMs 351322 Specdb::CMs 351323 Specdb::CMs 351324 Specdb::CMs 351325 Specdb::CMs 351326 Specdb::CMs 351327 Specdb::CMs 351328 Specdb::CMs 351329 Specdb::CMs 351330 Specdb::CMs 351331 Specdb::CMs 351332 Specdb::CMs 351333 Specdb::CMs 351334 Specdb::CMs 351335 Specdb::CMs 351336 Specdb::CMs 351337 Specdb::CMs 351338 Specdb::NmrOneD 69812 Specdb::NmrOneD 69813 Specdb::NmrOneD 69814 Specdb::NmrOneD 69815 Specdb::NmrOneD 69816 Specdb::NmrOneD 69817 Specdb::NmrOneD 69818 Specdb::NmrOneD 69819 Specdb::NmrOneD 69820 Specdb::NmrOneD 69821 Specdb::NmrOneD 69822 Specdb::NmrOneD 69823 Specdb::NmrOneD 69824 Specdb::NmrOneD 69825 Specdb::NmrOneD 69826 Specdb::NmrOneD 69827 Specdb::NmrOneD 69828 Specdb::NmrOneD 69829 Specdb::NmrOneD 69830 Specdb::NmrOneD 69831 Specdb::MsMs 1284094 Specdb::MsMs 1284095 Specdb::MsMs 1284096 Specdb::MsMs 1398916 Specdb::MsMs 1398917 Specdb::MsMs 1398918 Specdb::MsMs 2721162 Specdb::MsMs 2721163 Specdb::MsMs 2721164 Specdb::MsMs 2960166 Specdb::MsMs 2960167 Specdb::MsMs 2960168 25202390 26233430 DTDP-D-GLUCOSE 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 dTDP-glucose 4,6-dehydratase 2 P27830 RMLB2_ECOLI rffG http://ecmdb.ca/proteins/P27830.xml Glucose-1-phosphate thymidylyltransferase 1 P37744 RMLA1_ECOLI rmlA1 http://ecmdb.ca/proteins/P37744.xml dTDP-glucose 4,6-dehydratase 1 P37759 RMLB1_ECOLI rfbB http://ecmdb.ca/proteins/P37759.xml Glucose-1-phosphate thymidylyltransferase 2 P61887 RMLA2_ECOLI rmlA2 http://ecmdb.ca/proteins/P61887.xml TDP-Glucose > dTDP-4-dehydro-6-deoxy-D-glucose + Water PW_R005975 Glucose 1-phosphate + Thymidine 5'-triphosphate + Hydrogen ion > Pyrophosphate + TDP-Glucose PW_R005974