2.02012-05-31 13:51:17 -06002015-06-03 15:54:04 -0600ECMDB01376M2MDB0003632-Keto-3-deoxy-6-phosphogluconic acid2-Keto-3-deoxy-6-phosphogluconic acid is a substrate for Fructose-bisphosphate aldolase A.2-Dehydro-3-deoxy-6-phospho-D-gluconate2-Dehydro-3-deoxy-6-phospho-D-gluconic acid2-dehydro-3-Deoxy-D-gluconate 6-phosphate2-Dehydro-3-deoxy-D-gluconate-6-phosphate2-dehydro-3-Deoxy-D-gluconic acid-6-phosphoric acid2-Keto-3-deoxy-6-P-gluconate2-Keto-3-deoxy-6-P-gluconic acid2-Keto-3-deoxy-6-phospho-D-gluconate2-Keto-3-deoxy-6-phospho-D-gluconic acid2-Keto-3-deoxy-6-phospho-Gluconate2-Keto-3-deoxy-6-phospho-Gluconic acid2-Keto-3-deoxy-6-phosphogluconate2-Keto-3-deoxy-6-phosphogluconic acid2-Keto-3-deoxygluconate-6-P2-keto-3-Deoxygluconic acid-6-P3-deoxy-D-<i>erythro</i>-hex-2-ulosonate-6-phosphate3-deoxy-D-<i>erythro</i>-hex-2-ulosonic acid 6-phosphate3-Deoxy-D-erythro-hex-2-ulosonate 6-phosphate3-Deoxy-D-erythro-hex-2-ulosonate-6-phosphate3-Deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate3-Deoxy-D-erythro-hex-2-ulosonic acid 6-phosphoric acid3-Deoxy-D-erythro-hex-2-ulosonic acid-6-phosphoric acid6-p-2-k-3-Deo-gluconate6-p-2-k-3-Deo-gluconic acid6-Phospho-2-dehydro-3-deoxy-D-gluconate6-Phospho-2-dehydro-3-deoxy-D-gluconic acid6-Phospho-2-dehydro-3-deoxygluconate6-Phospho-2-dehydro-3-deoxygluconic acid6-Phospho-2-keto-3-deoxygluconate6-Phospho-2-keto-3-deoxygluconic acidKDPGlcAC6H11O9P258.1199258.014068462(4S,5R)-4,5-dihydroxy-2-oxo-6-(phosphonooxy)hexanoic acidkdpg intermediate27244-54-8O[C@H](COP(O)(O)=O)[C@@H](O)CC(=O)C(O)=OInChI=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)/t3-,5+/m0/s1OVPRPPOVAXRCED-WVZVXSGGSA-NSolidCytosollogp-2.36logs-1.26solubility1.43e+01 g/llogp-1.9pka_strongest_acidic1.48pka_strongest_basic-3.3iupac(4S,5R)-4,5-dihydroxy-2-oxo-6-(phosphonooxy)hexanoic acidaverage_mass258.1199mono_mass258.014068462smilesO[C@H](COP(O)(O)=O)[C@@H](O)CC(=O)C(O)=OformulaC6H11O9PinchiInChI=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)/t3-,5+/m0/s1inchikeyOVPRPPOVAXRCED-WVZVXSGGSA-Npolar_surface_area161.59refractivity47.19polarizability20.17rotatable_bond_count7acceptor_count8donor_count5physiological_charge-3formal_charge0Pentose phosphate pathwayec00030Arginine and proline metabolismec00330Pentose and glucuronate interconversionsec00040Glyoxylate and dicarboxylate metabolismec00630Microbial metabolism in diverse environmentsec01120Metabolic pathwayseco01100hexuronide and hexuronate degradationE. 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.PW000834Metabolicketogluconate metabolismPW002003MetabolicEntner-Doudoroff pathway IENTNER-DOUDOROFF-PWYβ-D-glucuronide and D-glucuronate degradationGLUCUROCAT-PWYD-galacturonate degradation IGALACTUROCAT-PWYSpecdb::CMs25704Specdb::CMs38044Specdb::CMs160207Specdb::NmrOneD87972Specdb::NmrOneD87973Specdb::NmrOneD87974Specdb::NmrOneD87975Specdb::NmrOneD87976Specdb::NmrOneD87977Specdb::NmrOneD87978Specdb::NmrOneD87979Specdb::NmrOneD87980Specdb::NmrOneD87981Specdb::NmrOneD87982Specdb::NmrOneD87983Specdb::NmrOneD87984Specdb::NmrOneD87985Specdb::NmrOneD87986Specdb::NmrOneD87987Specdb::NmrOneD87988Specdb::NmrOneD87989Specdb::NmrOneD87990Specdb::NmrOneD87991Specdb::MsMs25796Specdb::MsMs25797Specdb::MsMs25798Specdb::MsMs32354Specdb::MsMs32355Specdb::MsMs32356Specdb::MsMs2818422Specdb::MsMs2818423Specdb::MsMs2818424Specdb::MsMs2887837Specdb::MsMs2887838Specdb::MsMs2887839HMDB0137630807452338483C04442159252-KETO-3-DEOXY-6-P-GLUCONATEKeseler, 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-D114.22080510van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064KHG/KDPG aldolaseP0A955ALKH_ECOLIedahttp://ecmdb.ca/proteins/P0A955.xmlPhosphogluconate dehydrataseP0ADF6EDD_ECOLIeddhttp://ecmdb.ca/proteins/P0ADF6.xml2-dehydro-3-deoxygluconokinaseP37647KDGK_ECOLIkdgKhttp://ecmdb.ca/proteins/P37647.xml2-Keto-3-deoxy-6-phosphogluconic acid <> D-Glyceraldehyde 3-phosphate + Pyruvic acidR05605KDPGALDOL-RXN6-Phosphogluconic acid <> 2-Keto-3-deoxy-6-phosphogluconic acid + WaterR02036PGLUCONDEHYDRAT-RXN2-Keto-3-deoxy-D-gluconic acid + Adenosine triphosphate <> 2-Keto-3-deoxy-6-phosphogluconic acid + ADP + Hydrogen ionR01541DEOXYGLUCONOKIN-RXNAdenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid <> ADP + 2-Keto-3-deoxy-6-phosphogluconic acidR015412-Keto-3-deoxy-D-gluconic acid + Adenosine triphosphate > Hydrogen ion + 2-Keto-3-deoxy-6-phosphogluconic acid + ADPDEOXYGLUCONOKIN-RXN2-Keto-3-deoxy-6-phosphogluconic acid > D-Glyceraldehyde 3-phosphate + Pyruvic acidKDPGALDOL-RXN6-Phosphogluconic acid > 2-Keto-3-deoxy-6-phosphogluconic acid + WaterR02036PGLUCONDEHYDRAT-RXNAdenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid > ADP + 2-Keto-3-deoxy-6-phosphogluconic acid2-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 + ADPPW_R0030642-Keto-3-deoxy-6-phosphogluconic acid > D-Glyceraldehyde 3-phosphate + Pyruvic acid + D-Glyceraldehyde 3-phosphatePW_R003065gluconate 6-phosphate > Water + 2-Keto-3-deoxy-6-phosphogluconic acidPW_R0057006 6-Phosphogluconic acid <>2 2-Keto-3-deoxy-6-phosphogluconic acid + Water