2.0 2012-05-31 14:29:36 -0600 2015-06-03 17:19:23 -0600 ECMDB20140 M2MDB000988 D-Galactonate D-galactonate is a member of the chemical class known as Sugar Acids and Derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group. The gluconic acid is produced by direct extracellular oxidation of glucose by a glucose dehydrogenase equipped with pyrroloquinoline quinone (PQQ) as a cofactor. (PMID 14756528) Glucuronate is converted to l-gulonate by aldehyde reductase, an enzyme of the aldo-keto reductase superfamily. l-Gulonate is converted to l-gulonolactone by a lactonase identified as SMP30 or regucalcin, whose absence in mice leads to vitamin C deficiency. (PMID 17222174) (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoate (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid 2,3,4,5,6-Pentahydroxyhexanoate 2,3,4,5,6-Pentahydroxyhexanoic acid Altronate Altronic acid D-Altronate D-Altronic acid D-Galactonate D-Galactonic acid D-Gluco-hexonate D-Gluco-hexonic acid D-Gluconate D-Gluconic acid D-Mannonate D-Mannonic acid Galactonate Galactonic acid Gluconate Gluconate, technical Gluconic acid Gluconic acid, technical Gulonate Gulonic acid Hexonate Hexonic acid L-Galactonate L-Galactonic acid L-Gulonate L-Gulonic acid L-Idonate L-Idonic acid Mannonate Mannonic acid C6H12O7 196.1553 196.058302738 2,3,4,5,6-pentahydroxyhexanoic acid magnesium gluconate anhydrous 133-42-6 OCC(O)C(O)C(O)C(O)C(O)=O InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13) RGHNJXZEOKUKBD-UHFFFAOYSA-N Cytosol Extra-organism Periplasm logp -2.57 ALOGPS logs -0.09 ALOGPS solubility 1.59e+02 g/l ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 3.39 ChemAxon pka_strongest_basic -3 ChemAxon iupac 2,3,4,5,6-pentahydroxyhexanoic acid ChemAxon average_mass 196.1553 ChemAxon mono_mass 196.058302738 ChemAxon smiles OCC(O)C(O)C(O)C(O)C(O)=O ChemAxon formula C6H12O7 ChemAxon inchi InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13) ChemAxon inchikey RGHNJXZEOKUKBD-UHFFFAOYSA-N ChemAxon polar_surface_area 138.45 ChemAxon refractivity 38.27 ChemAxon polarizability 16.83 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 6 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 D-galactonate degradation GALACTCAT-PWY Specdb::CMs 98629 Specdb::CMs 120006 Specdb::CMs 919642 Specdb::CMs 919643 Specdb::CMs 919644 Specdb::CMs 919645 Specdb::CMs 919646 Specdb::CMs 919647 Specdb::CMs 919648 Specdb::CMs 919649 Specdb::CMs 919650 Specdb::CMs 919651 Specdb::CMs 919652 Specdb::CMs 919653 Specdb::CMs 919654 Specdb::CMs 919655 Specdb::CMs 919656 Specdb::CMs 919657 Specdb::CMs 919658 Specdb::CMs 919659 Specdb::CMs 919660 Specdb::CMs 919661 Specdb::CMs 919662 Specdb::CMs 919663 Specdb::CMs 919664 Specdb::NmrOneD 221057 Specdb::NmrOneD 221058 Specdb::NmrOneD 221059 Specdb::NmrOneD 221060 Specdb::NmrOneD 221061 Specdb::NmrOneD 221062 Specdb::NmrOneD 221063 Specdb::NmrOneD 221064 Specdb::NmrOneD 221065 Specdb::NmrOneD 221066 Specdb::NmrOneD 221067 Specdb::NmrOneD 221068 Specdb::NmrOneD 221069 Specdb::NmrOneD 221070 Specdb::NmrOneD 221071 Specdb::NmrOneD 221072 Specdb::NmrOneD 221073 Specdb::NmrOneD 221074 Specdb::NmrOneD 221075 Specdb::NmrOneD 221076 Specdb::MsMs 28028 Specdb::MsMs 28029 Specdb::MsMs 28030 Specdb::MsMs 34586 Specdb::MsMs 34587 Specdb::MsMs 34588 Specdb::MsMs 3441463 Specdb::MsMs 3441464 Specdb::MsMs 3441465 Specdb::MsMs 3441466 Specdb::MsMs 3441467 Specdb::MsMs 3441468 HMDB00565 604 584 C15930 12931 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 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 Linster, C. L., Van Schaftingen, E. (2007). "Vitamin C. Biosynthesis, recycling and degradation in mammals." FEBS J 274:1-22. 17222174 Kim, C. H., Han, S. H., Kim, K. Y., Cho, B. H., Kim, Y. H., Koo, B. S., Kim, Y. C. (2003). "Cloning and expression of pyrroloquinoline quinone (PQQ) genes from a phosphate-solubilizing bacterium Enterobacter intermedium." Curr Microbiol 47:457-461. 14756528 Glyoxylate/hydroxypyruvate reductase B P37666 GHRB_ECOLI ghrB http://ecmdb.ca/proteins/P37666.xml L-idonate 5-dehydrogenase P39346 IDND_ECOLI idnD http://ecmdb.ca/proteins/P39346.xml D-galactonate dehydratase Q6BF17 DGOD_ECOLI dgoD http://ecmdb.ca/proteins/Q6BF17.xml Putative L-galactonate oxidoreductase P39400 YJJN_ECOLI yjjN http://ecmdb.ca/proteins/P39400.xml D-galactonate transporter P0AA76 DGOT_ECOLI dgoT http://ecmdb.ca/proteins/P0AA76.xml Gnt-II system L-idonate transporter P39344 IDNT_ECOLI idnT http://ecmdb.ca/proteins/P39344.xml L-galactonate transporter P39398 YJJL_ECOLI yjjL http://ecmdb.ca/proteins/P39398.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml 2 -Dehydro-L-gulonate + Hydrogen ion + NADH > D-Galactonate + NAD 2 -Dehydro-L-gulonate + Hydrogen ion + NADPH > D-Galactonate + NADP 5-Keto-D-gluconate + Hydrogen ion + NADH <> D-Galactonate + NAD 5-Keto-D-gluconate + Hydrogen ion + NADPH > D-Galactonate + NADP D-Galactonate + NAD > Hydrogen ion + NADH + 5-Keto-D-gluconate D-Galactonate > Water + 2-Dehydro-3-deoxy-D-galactonate GALACTONDEHYDRAT-RXN