2.02012-05-31 14:29:30 -06002015-06-03 17:19:23 -0600ECMDB20138M2MDB000986D-FructuronateD-fructuronate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. One of the most divergent members of this superfamily, uronate isomerase from Escherichia coli, catalyzes the isomerization of d-glucuronate to d-fructuronate and d-galacturonate to d-tagaturonate and is the only uronate isomerase in this organism. (PMID 18171028)D-Fructofuranuronic aicdD-Fructuronic acidD-Lyxo-hex-5-ulofuranosonateD-Lyxo-hex-5-ulofuranosonic acidFructuronateFructuronic acidC6H10O7194.1394194.042652674(2S,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolane-2-carboxylic acidD-fructuronate669-90-9[H][C@]1(O)[C@]([H])(O)C(O)(CO)O[C@]1([H])C(O)=OInChI=1S/C6H10O7/c7-1-6(12)4(9)2(8)3(13-6)5(10)11/h2-4,7-9,12H,1H2,(H,10,11)/t2-,3+,4+,6?/m1/s1PTCIWUZVDIQTOW-XDJBDKDSSA-NCytosolExtra-organismPeriplasmlogp-1.94logs0.52solubility6.37e+02 g/llogp-2.4pka_strongest_acidic3.21pka_strongest_basic-3.5iupac(2S,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolane-2-carboxylic acidaverage_mass194.1394mono_mass194.042652674smiles[H][C@]1(O)[C@]([H])(O)C(O)(CO)O[C@]1([H])C(O)=OformulaC6H10O7inchiInChI=1S/C6H10O7/c7-1-6(12)4(9)2(8)3(13-6)5(10)11/h2-4,7-9,12H,1H2,(H,10,11)/t2-,3+,4+,6?/m1/s1inchikeyPTCIWUZVDIQTOW-XDJBDKDSSA-Npolar_surface_area127.45refractivity36.23polarizability16.4rotatable_bond_count2acceptor_count7donor_count5physiological_charge-1formal_charge0Pentose and glucuronate interconversionsec00040Metabolic 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.PW000834Metabolicinner membrane transportlist 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 addedPW000786Metabolicβ-D-glucuronide and D-glucuronate degradationGLUCUROCAT-PWYSpecdb::CMs1083534Specdb::EiMs3211Specdb::NmrOneD257948Specdb::NmrOneD257949Specdb::NmrOneD257950Specdb::NmrOneD257951Specdb::NmrOneD257952Specdb::NmrOneD257953Specdb::NmrOneD257954Specdb::NmrOneD257955Specdb::NmrOneD257956Specdb::NmrOneD257957Specdb::NmrOneD257958Specdb::NmrOneD257959Specdb::NmrOneD257960Specdb::NmrOneD257961Specdb::NmrOneD257962Specdb::NmrOneD257963Specdb::NmrOneD257964Specdb::NmrOneD257965Specdb::NmrOneD257966Specdb::NmrOneD257967Specdb::MsMs29090Specdb::MsMs29091Specdb::MsMs29092Specdb::MsMs35648Specdb::MsMs35649Specdb::MsMs35650439343388470C0090516849FRUCTURONATEKeseler, 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-D114.22080510Nguyen, T. T., Brown, S., Fedorov, A. A., Fedorov, E. V., Babbitt, P. C., Almo, S. C., Raushel, F. M. (2008). "At the periphery of the amidohydrolase superfamily: Bh0493 from Bacillus halodurans catalyzes the isomerization of D-galacturonate to D-tagaturonate." Biochemistry 47:1194-1206.18171028Uronate isomeraseP0A8G3UXAC_ECOLIuxaChttp://ecmdb.ca/proteins/P0A8G3.xmlD-mannonate oxidoreductaseP39160UXUB_ECOLIuxuBhttp://ecmdb.ca/proteins/P39160.xmlStarvation-sensing protein RspBP38105RSPB_ECOLIrspBhttp://ecmdb.ca/proteins/P38105.xmlHigh-affinity gluconate transporterP0AC94GNTP_ECOLIgntPhttp://ecmdb.ca/proteins/P0AC94.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlD-Glucuronic acid <> D-FructuronateR01482GLUCUROISOM-RXND-Mannonate + NAD <> D-Fructuronate + Hydrogen ion + NADHR02454MANNONOXIDOREDUCT-RXND-Glucuronic acid > D-FructuronateD-Mannonate + NAD > D-Fructuronate + NADHL-Gulonate + NAD <> D-Fructuronate + NADH + Hydrogen ionR10848 aldehydo-D-glucuronate > D-FructuronatePW_R003058D-Fructuronate + NADH + Hydrogen ion > NAD + D-altronatePW_R003059