2.0 2012-05-31 13:50:40 -0600 2015-09-17 19:21:29 -0600 ECMDB01353 M2MDB000352 2-Keto-3-deoxy-D-gluconic acid 2-keto-3-deoxy-D-gluconic acid is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. KDG, an actual inducer of pectinolysis, releases the repressor from the operator complexes, whereas galacturonate, which is the precursor of the actual inducer, does not. (PMID 1545709) KDG aldolase, KDGA, is a homotetramer of 32-kDa subunits. (PMID 20023024) The KDG-aldolase is a thermostable tetrameric protein with a half-life at 100 degrees C of 2. (PMID 10527934) 2-Dehydro-3-deoxy-D-gluconate 2-Dehydro-3-deoxy-D-gluconic acid 2-Keto-3-deoxy-D-gluconate 2-Keto-3-deoxy-D-gluconic acid 2-Keto-3-deoxygluconate 2-Keto-3-deoxygluconic acid 3-Deoxy-2-oxo-D-gluconate 3-Deoxy-2-oxo-D-gluconic acid 3-deoxy-D-<i>erythro</i>-hex-2-ulosonic acid 3-Deoxy-D-erythro-2-hexulosonate 3-Deoxy-D-erythro-2-hexulosonic acid 3-Deoxy-D-erythro-hex-2-ulosonate 3-Deoxy-D-erythro-hex-2-ulosonic acid KDG C6H10O6 178.14 178.047738052 (4S,5R)-4,5,6-trihydroxy-2-oxohexanoic acid 2-dehydro-3-deoxy-D-gluconate 17510-99-5 OC[C@@H](O)[C@H](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)/t3-,5-/m1/s1 WPAMZTWLKIDIOP-NQXXGFSBSA-N Cytosol Extra-organism Periplasm 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 (4S,5R)-4,5,6-trihydroxy-2-oxohexanoic acid ChemAxon average_mass 178.14 ChemAxon mono_mass 178.047738052 ChemAxon smiles OC[C@@H](O)[C@H](O)CC(=O)C(O)=O ChemAxon formula C6H10O6 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)/t3-,5-/m1/s1 ChemAxon inchikey WPAMZTWLKIDIOP-NQXXGFSBSA-N ChemAxon polar_surface_area 115.06 ChemAxon refractivity 36.32 ChemAxon polarizability 15.52 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Pentose and glucuronate interconversions ec00040 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 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 &beta;-D-glucuronide and D-glucuronate degradation GLUCUROCAT-PWY D-galacturonate degradation I GALACTUROCAT-PWY Specdb::CMs 1084341 Specdb::MsMs 29039 Specdb::MsMs 29040 Specdb::MsMs 29041 Specdb::MsMs 35597 Specdb::MsMs 35598 Specdb::MsMs 35599 HMDB01353 141630 C00204 2-DEHYDRO-3-DEOXY-D-GLUCONATE KDG 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 Nasser, W., Reverchon, S., Robert-Baudouy, J. (1992). "Purification and functional characterization of the KdgR protein, a major repressor of pectinolysis genes of Erwinia chrysanthemi." Mol Microbiol 6:257-265. 1545709 Buchanan, C. L., Connaris, H., Danson, M. J., Reeve, C. D., Hough, D. W. (1999). "An extremely thermostable aldolase from Sulfolobus solfataricus with specificity for non-phosphorylated substrates." Biochem J 343 Pt 3:563-570. 10527934 Reher, M., Fuhrer, T., Bott, M., Schonheit, P. (2010). "The nonphosphorylative Entner-Doudoroff pathway in the thermoacidophilic euryarchaeon Picrophilus torridus involves a novel 2-keto-3-deoxygluconate- specific aldolase." J Bacteriol 192:964-974. 20023024 2-keto-3-deoxygluconate permease P0A712 KDGT_ECOLI kdgT http://ecmdb.ca/proteins/P0A712.xml Mannonate dehydratase P24215 UXUA_ECOLI uxuA http://ecmdb.ca/proteins/P24215.xml 2-dehydro-3-deoxygluconokinase P37647 KDGK_ECOLI kdgK http://ecmdb.ca/proteins/P37647.xml 2-dehydro-3-deoxy-D-gluconate 5-dehydrogenase P37769 KDUD_ECOLI kduD http://ecmdb.ca/proteins/P37769.xml Altronate hydrolase P42604 UXAA_ECOLI uxaA http://ecmdb.ca/proteins/P42604.xml Starvation-sensing protein RspA P38104 RSPA_ECOLI rspA http://ecmdb.ca/proteins/P38104.xml 2-keto-3-deoxygluconate permease P0A712 KDGT_ECOLI kdgT http://ecmdb.ca/proteins/P0A712.xml 2-keto-3-deoxygluconate permease B1XB76 KDGT_ECODH kdgT http://ecmdb.ca/proteins/B1XB76.xml 2-keto-3-deoxygluconate permease C5A077 KDGT_ECOBW kdgT http://ecmdb.ca/proteins/C5A077.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 D-Altronate <> 2-Keto-3-deoxy-D-gluconic acid + Water R01540 ALTRODEHYDRAT-RXN 2-Keto-3-deoxy-D-gluconic acid + Adenosine triphosphate <> 2-Keto-3-deoxy-6-phosphogluconic acid + ADP + Hydrogen ion R01541 DEOXYGLUCONOKIN-RXN D-Mannonate <> 2-Keto-3-deoxy-D-gluconic acid + Water R05606 MANNONDEHYDRAT-RXN Adenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid <> ADP + 2-Keto-3-deoxy-6-phosphogluconic acid R01541 2-Keto-3-deoxy-D-gluconic acid + NAD <> (4S)-4,6-Dihydroxy-2,5-dioxohexanoate + NADH + Hydrogen ion R01542 D-Altronate > Water + 2-Keto-3-deoxy-D-gluconic acid ALTRODEHYDRAT-RXN 2-Keto-3-deoxy-D-gluconic acid + Adenosine triphosphate > Hydrogen ion + 2-Keto-3-deoxy-6-phosphogluconic acid + ADP DEOXYGLUCONOKIN-RXN 2-Keto-3-deoxy-D-gluconic acid D-Glyceraldehyde + Pyruvic acid DHDOGALDOL-RXN D-Mannonate > Water + 2-Keto-3-deoxy-D-gluconic acid MANNONDEHYDRAT-RXN Adenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid > ADP + 2-Keto-3-deoxy-6-phosphogluconic acid 2-Keto-3-deoxy-D-gluconic acid + NAD > (4S)-4,6-Dihydroxy-2,5-dioxohexanoate + NADH 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