2.0 2012-05-31 14:03:16 -0600 2015-06-03 15:54:40 -0600 ECMDB04045 M2MDB000578 2-Dehydro-3-deoxy-D-galactonate-6-phosphate 2-Dehydro-3-deoxy-D-galactonate-6-phosphate is an intermediate in D-galactonate degradation. It is a substrate for the enzyme 2-dehydro-3-deoxygalactonokinase. This enzyme 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-6-phosphoric acid 2-Keto-3-deoxy-D-galactonate-6-phosphate 2-keto-3-Deoxy-D-galactonic acid-6-phosphoric acid Dehydro-deoxy-galactonate-phosphate dehydro-Deoxy-galactonic acid-phosphoric acid C6H8O9P 255.0961 254.990593366 (4R,5R)-4,5-dihydroxy-2-oxo-6-(phosphonatooxy)hexanoate (4R,5R)-4,5-dihydroxy-2-oxo-6-(phosphonatooxy)hexanoate 32120-43-7 [H][C@@](O)(COP([O-])([O-])=O)[C@]([H])(O)CC(=O)C([O-])=O InChI=1S/C6H11O9P/c7-3(1-4(8)6(10)11)5(9)2-15-16(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H2,12,13,14)/p-3/t3-,5-/m1/s1 OVPRPPOVAXRCED-NQXXGFSBSA-K Cytosol logp -1.35 ALOGPS logs -0.80 ALOGPS solubility 4.85e+01 g/l ALOGPS logp -1.9 ChemAxon pka_strongest_acidic 1.48 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (4R,5R)-4,5-dihydroxy-2-oxo-6-(phosphonatooxy)hexanoate ChemAxon average_mass 255.0961 ChemAxon mono_mass 254.990593366 ChemAxon smiles [H][C@@](O)(COP([O-])([O-])=O)[C@]([H])(O)CC(=O)C([O-])=O ChemAxon formula C6H8O9P ChemAxon inchi InChI=1S/C6H11O9P/c7-3(1-4(8)6(10)11)5(9)2-15-16(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H2,12,13,14)/p-3/t3-,5-/m1/s1 ChemAxon inchikey OVPRPPOVAXRCED-NQXXGFSBSA-K ChemAxon polar_surface_area 170.08 ChemAxon refractivity 55.78 ChemAxon polarizability 19.09 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 8 ChemAxon donor_count 2 ChemAxon physiological_charge -3 ChemAxon formal_charge -3 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 Metabolic pathways eco01100 D-galactonate degradation GALACTCAT-PWY Specdb::NmrOneD 323152 Specdb::NmrOneD 323153 Specdb::NmrOneD 323154 Specdb::NmrOneD 323155 Specdb::NmrOneD 323156 Specdb::NmrOneD 323157 Specdb::NmrOneD 323158 Specdb::NmrOneD 323159 Specdb::NmrOneD 323160 Specdb::NmrOneD 323161 Specdb::NmrOneD 323162 Specdb::NmrOneD 323163 Specdb::NmrOneD 323164 Specdb::NmrOneD 323165 Specdb::NmrOneD 323166 Specdb::NmrOneD 323167 Specdb::NmrOneD 323168 Specdb::NmrOneD 323169 Specdb::NmrOneD 323170 Specdb::NmrOneD 323171 Specdb::MsMs 28997 Specdb::MsMs 28998 Specdb::MsMs 28999 Specdb::MsMs 35555 Specdb::MsMs 35556 Specdb::MsMs 35557 44229080 26331111 C01286 17860 DEHYDRO-DEOXY-GALACTONATE-PHOSPHATE 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 2-dehydro-3-deoxygalactonokinase P31459 DGOK_ECOLI dgoK http://ecmdb.ca/proteins/P31459.xml 2-dehydro-3-deoxy-6-phosphogalactonate aldolase Q6BF16 DGOA_ECOLI dgoA http://ecmdb.ca/proteins/Q6BF16.xml 2-Dehydro-3-deoxy-D-galactonate + Adenosine triphosphate <> 2-Dehydro-3-deoxy-D-galactonate-6-phosphate + ADP + Hydrogen ion R03387 DEHYDDEOXGALACTKIN-RXN 2-Dehydro-3-deoxy-D-galactonate-6-phosphate <> D-Glyceraldehyde 3-phosphate + Pyruvic acid R01064 DEHYDDEOXPHOSGALACT-ALDOL-RXN 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