2.0 2012-05-31 14:03:13 -0600 2015-09-17 15:42:01 -0600 ECMDB04044 M2MDB000577 2-Dehydro-3-deoxy-D-galactonate 2-Dehydro-3-deoxy-D-galactonate is a carbohydrate acid. It is an intermediate in carbohydrate-acid metabolism and D-galactonate metabolism. It is a substrate for 2-dehydro-3-deoxygalactonokinase which catalyzes the following reaction: ATP + 2-dehydro-3-deoxy-D-galactonate = ADP + 2-dehydro-3-deoxy-D-galactonate 6-phosphate. 2-Dehydro-3-deoxy-D-galactonic acid 2-Dehydro-3-deoxygalactonate 2-Dehydro-3-deoxygalactonic acid 2-Keto-3-deoxy-D-galactonate 2-Keto-3-deoxy-D-galactonic acid 2-Keto-3-deoxygalactonate 2-Keto-3-deoxygalactonic acid C6H9O6 177.133 177.04046159 (4R,5R)-4,5,6-trihydroxy-2-oxohexanoic acid (4R,5R)-4,5,6-trihydroxy-2-oxohexanoic acid OCC(O)C(O)CC(=O)C([O-])=O InChI=1S/C6H10O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,5,7-8,10H,1-2H2,(H,11,12)/p-1 WPAMZTWLKIDIOP-UHFFFAOYSA-M Cytosol logp -1.87 ALOGPS logs -0.12 ALOGPS solubility 1.34e+02 g/l ALOGPS logp -1.8 ChemAxon pka_strongest_acidic 2.91 ChemAxon pka_strongest_basic -3 ChemAxon iupac (4R,5R)-4,5,6-trihydroxy-2-oxohexanoic acid ChemAxon average_mass 177.133 ChemAxon mono_mass 177.04046159 ChemAxon smiles OCC(O)C(O)CC(=O)C([O-])=O ChemAxon formula C6H9O6 ChemAxon inchi InChI=1S/C6H10O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,5,7-8,10H,1-2H2,(H,11,12)/p-1 ChemAxon inchikey WPAMZTWLKIDIOP-UHFFFAOYSA-M ChemAxon polar_surface_area 115.06 ChemAxon refractivity 36.32 ChemAxon polarizability 15.54 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Galactose metabolism Galactose can be synthesized through two pathways: melibiose degradation involving an alpha galactosidase and lactose degradation involving a beta galactosidase. Melibiose is first transported inside the cell through the melibiose:Li+/Na+/H+ symporter. Once inside the cell, melibiose is degraded through alpha galactosidase into an alpha-D-galactose and a beta-D-glucose. The beta-D-glucose is phosphorylated by a glucokinase to produce a beta-D-glucose-6-phosphate which can spontaneously be turned into a alpha D glucose 6 phosphate. This alpha D-glucose-6-phosphate is metabolized into a glucose -1-phosphate through a phosphoglucomutase-1. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase. Galactose can also be produced by lactose degradation involving a lactose permease to uptake lactose from the environment and a beta-galactosidase to turn lactose into Beta-D-galactose. Beta-D-galactose can also be uptaken from the environment through a galactose proton symporter. Galactose is degraded through the following process: Beta-D-galactose is introduced into the cytoplasm through a galactose proton symporter, or it can be synthesized from an alpha lactose that is introduced into the cytoplasm through a lactose permease. Alpha lactose interacts with water through a beta-galactosidase resulting in a beta-D-glucose and beta-D-galactose. Beta-D-galactose is isomerized into D-galactose. D-Galactose undergoes phosphorylation through a galactokinase, hence producing galactose 1 phosphate. On the other side of the pathway, a gluose-1-phosphate (product of the interaction of alpha-D-glucose 6-phosphate with a phosphoglucomutase resulting in a alpha-D-glucose-1-phosphate, an isomer of Glucose 1-phosphate, or an isomer of Beta-D-glucose 1-phosphate) interacts with UTP and a hydrogen ion in order to produce a uridine diphosphate glucose. This is followed by the interaction of galactose-1-phosphate with an established amount of uridine diphosphate glucose through a galactose-1-phosphate uridylyltransferase, which in turn output a glucose-1-phosphate and a uridine diphosphate galactose. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase, and so the cycle can keep going as long as more lactose or galactose is imported into the cell PW000821 ec00052 Metabolic Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Galactitol and galactonate degradation D-galactonate can serve as the sole source of carbon and energy for E. coli . The initial step, after the transport of galactonic acid into the cell is the degradation of D-galactonate is dehydration to 2-dehydro-3-deoxy-D-galactonate by D-galactonate dehydratase. Subsequent phosphorylation by 2-dehydro-3-deoxygalactonate kinase and aldol cleavage by 2-oxo-3-deoxygalactonate 6-phosphate aldolase produce pyruvate and D-glyceraldehyde-3-phosphate, which enter central metabolism. Galactitol can also be utilized by E. coli K-12 as a total source of carbon and energy. Each enters the cell via a specific phosphotransferase system, so the first intracellular species is D-galactitol-1-phosphate or D-galactitol-6-phosphate, which are identical. This sugar alcohol phosphate becomes the substrate for a dehydrogenase that oxidizes its 2-alcohol group to a keto group. Galactitol-1-phosphate, the product of the dehydrogenation is tagatose-6-phosphate, which becomes the substrate of a kinase and subsequently an aldolase (in a pair of reactions that parallel those of glycolysis) before it is converted into intermediates (D-glyceraldehde-3-phosphate and dihydroxy-acetone-phosphate) of glycolysis. PW000820 Metabolic hexuronide and hexuronate degradation E. coli can use β-D-glucuronosides, D-glucuronate and D-fructuronate as an only sources of carbon for growth. β-D-glucuronosides are detoxification products that are excreted into the mammalian gut in the bile. They enter E.coli through an outer membrane protein called gusC. Once in the periplasmic space it is transported through a hydrogen symporter into the cytoplasm. Once inside the cytoplasm, the initial step in the degradation of β-glucuronides is hydrolysis by β-D-glucuronidase to yield D-glucuronate. This is then isomerized to D-fructuronate by D-glucuronate isomerase. D-fructuronate then undergoes an NADH-dependent reduction to D-mannonate by D-mannonate oxidoreductase. D-mannonate dehydratase subsequently catalyzes dehydration to yield 2-dehydro-3-deoxy-D-gluconate. At this point, a common enzyme, 2-keto-3-deoxygluconokinase, phosphorylates 2-dehydro-3-deoxy-D-gluconate to yield 2-dehydro-3-deoxy-D-gluconate-6-phosphate.This product is then process by KHG/KDPG aldolase which in turn produces D-Glyceraldehyde 3-phosphate and Pyruvic Acid which then go into their respective sub pathways: glycolysis and pyruvate dehydrogenase The pathway can also start from 3 other points: a hydrogen ion symporter (gluconate/fructuronate transporter GntP) of D-fructuronate, a hydrogen ion symporter (Hexuronate transporter) of aldehydo-D-galacturonate that spontaneously turns into D-tagaturonate and then undergoes an NADH-dependent reduction to D-altronate through an altronate oxidoreductase. D-altronate undergoes dehydration to yield 2-dehydro-3-deoxy-D-gluconate, the third and last point where the reaction can start from a hydrogen symporter of a 2-dehydro-3-deoy-D-gluconate. PW000834 Metabolic inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 Metabolic D-galactonate degradation GALACTCAT-PWY Specdb::CMs 17516 Specdb::CMs 38037 Specdb::CMs 135041 Specdb::CMs 142775 Specdb::NmrOneD 87792 Specdb::NmrOneD 87793 Specdb::NmrOneD 87794 Specdb::NmrOneD 87795 Specdb::NmrOneD 87796 Specdb::NmrOneD 87797 Specdb::NmrOneD 87798 Specdb::NmrOneD 87799 Specdb::NmrOneD 87800 Specdb::NmrOneD 87801 Specdb::NmrOneD 87802 Specdb::NmrOneD 87803 Specdb::NmrOneD 87804 Specdb::NmrOneD 87805 Specdb::NmrOneD 87806 Specdb::NmrOneD 87807 Specdb::NmrOneD 87808 Specdb::NmrOneD 87809 Specdb::NmrOneD 87810 Specdb::NmrOneD 87811 Specdb::MsMs 25415 Specdb::MsMs 25416 Specdb::MsMs 25417 Specdb::MsMs 31973 Specdb::MsMs 31974 Specdb::MsMs 31975 Specdb::MsMs 2475047 Specdb::MsMs 2475048 Specdb::MsMs 2475049 Specdb::MsMs 2490845 Specdb::MsMs 2490846 Specdb::MsMs 2490847 37 36 C01216 17028 2-DEHYDRO-3-DEOXY-D-GALACTONATE 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 2-dehydro-3-deoxygalactonokinase P31459 DGOK_ECOLI dgoK http://ecmdb.ca/proteins/P31459.xml D-galactonate dehydratase Q6BF17 DGOD_ECOLI dgoD http://ecmdb.ca/proteins/Q6BF17.xml 2-Dehydro-3-deoxy-D-galactonate + Adenosine triphosphate <> 2-Dehydro-3-deoxy-D-galactonate-6-phosphate + ADP + Hydrogen ion R03387 DEHYDDEOXGALACTKIN-RXN Galactonic acid <> 2-Dehydro-3-deoxy-D-galactonate + Water R03033 Adenosine triphosphate + 2-Dehydro-3-deoxy-D-galactonate <> ADP + 2-Dehydro-3-deoxy-D-galactonate-6-phosphate R03387 2-Dehydro-3-deoxy-D-galactonate + Adenosine triphosphate > Hydrogen ion + 2-Dehydro-3-deoxy-D-galactonate-6-phosphate + ADP DEHYDDEOXGALACTKIN-RXN D-Galactonate > Water + 2-Dehydro-3-deoxy-D-galactonate GALACTONDEHYDRAT-RXN Galactonic acid > 2-Dehydro-3-deoxy-D-galactonate + Water Adenosine triphosphate + 2-Dehydro-3-deoxy-D-galactonate > ADP + 2-Dehydro-3-deoxy-D-galactonate 6-phosphate D-altronate > Water + 2-Dehydro-3-deoxy-D-galactonate + 2-Keto-3-deoxy-D-gluconic acid PW_R003060 D-altronate + D-altronate > Water + 2-Dehydro-3-deoxy-D-galactonate + 2-Keto-3-deoxy-D-gluconic acid PW_R003061 2-Dehydro-3-deoxy-D-galactonate + Adenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid > Hydrogen ion + 2-Keto-3-deoxy-6-phosphogluconic acid + Adenosine diphosphate + ADP PW_R003064 Galactonic acid + Galactonic acid > Water + 2-dehydro-3-deoxy-D-galactonate + 2-Dehydro-3-deoxy-D-galactonate PW_R002940 2-dehydro-3-deoxy-D-galactonate + Adenosine triphosphate + 2-Dehydro-3-deoxy-D-galactonate > Adenosine diphosphate + Hydrogen ion + 2-dehydro-3-deoxy-D-galactonate 6-phosphate + ADP + 2-Dehydro-3-deoxy-D-galactonate 6-phosphate PW_R002941