2.0 2012-07-30 14:55:31 -0600 2015-06-03 17:21:15 -0600 ECMDB21375 M2MDB001771 L-Galactonate L-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. A galactonate that is the conjugate base of L-galactonic acid. Galactonate Galactonic acid L-Galactonic acid C6H11O7 195.1473 195.050477706 (2S,3R,4R,5S)-2,3,4,5,6-pentahydroxyhexanoate L-galactonate [H][C@](O)(CO)[C@@]([H])(O)[C@@]([H])(O)[C@]([H])(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)/p-1/t2-,3+,4+,5-/m0/s1 RGHNJXZEOKUKBD-RSJOWCBRSA-M Cytoplasm logp -2.06 ALOGPS logs 0.39 ALOGPS solubility 5.20e+02 g/l ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 3.39 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S,3R,4R,5S)-2,3,4,5,6-pentahydroxyhexanoate ChemAxon average_mass 195.1473 ChemAxon mono_mass 195.050477706 ChemAxon smiles [H][C@](O)(CO)[C@@]([H])(O)[C@@]([H])(O)[C@]([H])(O)C([O-])=O ChemAxon formula C6H11O7 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)/p-1/t2-,3+,4+,5-/m0/s1 ChemAxon inchikey RGHNJXZEOKUKBD-RSJOWCBRSA-M ChemAxon polar_surface_area 141.28 ChemAxon refractivity 49.11 ChemAxon polarizability 16.61 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon 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 L-galactonate degradation PWY0-1306 Specdb::MsMs 23783 Specdb::MsMs 23784 Specdb::MsMs 23785 Specdb::MsMs 30581 Specdb::MsMs 30582 Specdb::MsMs 30583 44229140 26330589 C15930 53071 CPD0-1083 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 Putative L-galactonate oxidoreductase P39400 YJJN_ECOLI yjjN http://ecmdb.ca/proteins/P39400.xml L-galactonate transporter P39398 YJJL_ECOLI yjjL http://ecmdb.ca/proteins/P39398.xml L-Galactonate + NAD > Hydrogen ion + D-tagaturonate + NADH RXN0-5229 L-Galactonate + NAD > NADH + Hydrogen ion + D-Tagaturonate PW_R006012