2.02015-09-08 17:50:18 -06002015-09-14 16:46:08 -0600ECMDB24229M2MDB006346 D-altronateD-altronate 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. D-Altronic acidC6H11O7195.148195.0510262742,3,4,5,6-pentahydroxyhexanoate2,3,4,5,6-pentahydroxyhexanoateOCC(O)C(O)C(O)C(O)C([O-])=OInChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/p-1RGHNJXZEOKUKBD-UHFFFAOYSA-Mlogp-2.06logs0.39solubility5.20e+02 g/llogp-3.4pka_strongest_acidic3.39pka_strongest_basic-3iupac2,3,4,5,6-pentahydroxyhexanoateaverage_mass195.148mono_mass195.051026274smilesOCC(O)C(O)C(O)C(O)C([O-])=OformulaC6H11O7inchiInChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/p-1inchikeyRGHNJXZEOKUKBD-UHFFFAOYSA-Mpolar_surface_area141.28refractivity49.11polarizability16.55rotatable_bond_count5acceptor_count7donor_count5physiological_charge-1formal_charge-1hexuronide 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.PW000834MetabolicSpecdb::NmrOneD263768Specdb::NmrOneD263769Specdb::NmrOneD263770Specdb::NmrOneD263771Specdb::NmrOneD263772Specdb::NmrOneD263773Specdb::NmrOneD263774Specdb::NmrOneD263775Specdb::NmrOneD263776Specdb::NmrOneD263777Specdb::NmrOneD263778Specdb::NmrOneD263779Specdb::NmrOneD263780Specdb::NmrOneD263781Specdb::NmrOneD263782Specdb::NmrOneD263783Specdb::NmrOneD263784Specdb::NmrOneD263785Specdb::NmrOneD263786Specdb::NmrOneD263787Specdb::MsMs26126Specdb::MsMs26127Specdb::MsMs26128Specdb::MsMs32684Specdb::MsMs32685Specdb::MsMs32686Altronate oxidoreductaseP0A6L7UXAB_ECOLIuxaBhttp://ecmdb.ca/proteins/P0A6L7.xmlMannonate dehydrataseP24215UXUA_ECOLIuxuAhttp://ecmdb.ca/proteins/P24215.xmlD-mannonate oxidoreductaseP39160UXUB_ECOLIuxuBhttp://ecmdb.ca/proteins/P39160.xmlAltronate hydrolaseP42604UXAA_ECOLIuxaAhttp://ecmdb.ca/proteins/P42604.xmlD-Fructuronate + NADH + Hydrogen ion > NAD + D-altronatePW_R003059 D-altronate > Water + 2-Dehydro-3-deoxy-D-galactonate + 2-Keto-3-deoxy-D-gluconic acidPW_R003060 D-altronate + D-altronate > Water + 2-Dehydro-3-deoxy-D-galactonate + 2-Keto-3-deoxy-D-gluconic acidPW_R003061D-tagaturonate + NADH + Hydrogen ion + D-Tagaturonate > NAD + D-altronate + D-altronatePW_R003062