2.02012-05-31 14:24:18 -06002015-06-03 17:19:11 -0600ECMDB20040M2MDB0008892-Dehydro-3-deoxy-D-glucarate2-dehydro-3-deoxy-D-glucarate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. It is a substrate for 2-dehydro-3-deoxyglucarate aldolase (EC 4.1.2.20) which is an enzyme that catalyzes the chemical reaction: 2-dehydro-3-deoxy-D-glucarate = pyruvate + tartronate semialdehyde 2-Dehydro-3-deoxy-D-glucarate2-Dehydro-3-deoxy-D-glucaric acid2-Keto-3-deoxy-D-glucarate2-Keto-3-deoxy-D-glucaric acid2-Keto-3-deoxy-glucarate2-Keto-3-deoxy-glucaric acid3-Deoxy-D-erythro-hex-2-ulosarate3-Deoxy-D-erythro-hex-2-ulosaric acidKGRC6H8O7192.1235192.02700261(2S,3S)-2,3-dihydroxy-5-oxohexanedioic acid2-dehydro-3-deoxy-D-glucarate[H][C@](O)(CC(=O)C(O)=O)[C@]([H])(O)C(O)=OInChI=1S/C6H8O7/c7-2(4(9)6(12)13)1-3(8)5(10)11/h2,4,7,9H,1H2,(H,10,11)(H,12,13)/t2-,4-/m0/s1QUURPCHWPQNNGL-OKKQSCSOSA-NCytoplasmPeriplasmlogp-1.23logs-0.56solubility5.27e+01 g/llogp-1.5pka_strongest_acidic2.5pka_strongest_basic-3.3iupac(2S,3S)-2,3-dihydroxy-5-oxohexanedioic acidaverage_mass192.1235mono_mass192.02700261smiles[H][C@](O)(CC(=O)C(O)=O)[C@]([H])(O)C(O)=OformulaC6H8O7inchiInChI=1S/C6H8O7/c7-2(4(9)6(12)13)1-3(8)5(10)11/h2,4,7,9H,1H2,(H,10,11)(H,12,13)/t2-,4-/m0/s1inchikeyQUURPCHWPQNNGL-OKKQSCSOSA-Npolar_surface_area132.13refractivity36.18polarizability15.49rotatable_bond_count5acceptor_count7donor_count4physiological_charge-2formal_charge0Ascorbate and aldarate metabolismec00053Metabolic pathwayseco01100superpathway of D-glucarate and D-galactarate degradation
Galactarate is a naturally occurring dicarboxylic acid analog of D-galactose. E. coli can use both diacid sugars galactarate and D-glucarate as the sole source of carbon for growth.
The initial step in the degradation of galactarate is its dehydration to 5-dehydro-4-deoxy-D-glucarate(2--) by galactarate dehydratase. Glucaric acid can also be dehydrated by a glucarate dehydratase resulting in water and 5-dehydro-4-deoxy-D-glucarate(2--).
The 5-dehydro-4-deoxy-D-glucarate(2--) is then metabolized by a alpha-dehydro-beta-deoxy-D-glucarate aldolase resulting in pyruvic acid and a tartonate semialdehyde.
Pyruvic acid interacts with coenzyme A through a NAD driven Pyruvate dehydrogenase complex resulting in a carbon dioxide, an NADH and an acetyl-CoA.
The tartronate semialdehyde interacts with a hydrogen ion through a NADPH driven tartronate semialdehyde reductase resulting in a NADP and a glyceric acid. The glyceric acid is phosphorylated by an ATP-driven glycerate kinase 2 resulting in an ADP, a hydrogen ion and a 2-phosphoglyceric acid. The latter compound is dehydrated by an enolase resulting in the release of water and a phosphoenolpyruvic acid.
The phosphoenolpyruvic acid interacts with a hydrogen ion through an ADP driven pyruvate kinase resulting in an ATP and a pyruvic acid. The pyruvic acid then interacts with water and an ATP through a phosphoenolpyruvate synthetase resulting in the release of a hydrogen ion, a phosphate, an AMP and a Phosphoenolpyruvic acid.PW000795MetabolicSpecdb::CMs1084208Specdb::NmrOneD276658Specdb::NmrOneD276659Specdb::NmrOneD276660Specdb::NmrOneD276661Specdb::NmrOneD276662Specdb::NmrOneD276663Specdb::NmrOneD276664Specdb::NmrOneD276665Specdb::NmrOneD276666Specdb::NmrOneD276667Specdb::NmrOneD276668Specdb::NmrOneD276669Specdb::NmrOneD276670Specdb::NmrOneD276671Specdb::NmrOneD276672Specdb::NmrOneD276673Specdb::NmrOneD276674Specdb::NmrOneD276675Specdb::NmrOneD276676Specdb::NmrOneD276677Specdb::MsMs25391Specdb::MsMs25392Specdb::MsMs25393Specdb::MsMs31949Specdb::MsMs31950Specdb::MsMs31951440165389156C03921173052-KETO-3-DEOXY-D-GLUCARATEKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Glucarate dehydrataseP0AES2GUDH_ECOLIgudDhttp://ecmdb.ca/proteins/P0AES2.xml5-keto-4-deoxy-D-glucarate aldolaseP23522GARL_ECOLIgarLhttp://ecmdb.ca/proteins/P23522.xmlTartronate semialdehyde + Pyruvic acid <> 2-Dehydro-3-deoxy-D-glucarateR03277D-Glucarate <> 2-Dehydro-3-deoxy-D-glucarate + WaterR080562-Dehydro-3-deoxy-D-glucarate > Pyruvic acid + Tartronate semialdehydeGlucaric acid > Water + 2-Dehydro-3-deoxy-D-glucaratePW_R005867