2.0 2012-05-31 14:29:30 -0600 2015-06-03 17:19:23 -0600 ECMDB20138 M2MDB000986 D-Fructuronate D-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 aicd D-Fructuronic acid D-Lyxo-hex-5-ulofuranosonate D-Lyxo-hex-5-ulofuranosonic acid Fructuronate Fructuronic acid C6H10O7 194.1394 194.042652674 (2S,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolane-2-carboxylic acid D-fructuronate 669-90-9 [H][C@]1(O)[C@]([H])(O)C(O)(CO)O[C@]1([H])C(O)=O InChI=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/s1 PTCIWUZVDIQTOW-XDJBDKDSSA-N Cytosol Extra-organism Periplasm logp -1.94 ALOGPS logs 0.52 ALOGPS solubility 6.37e+02 g/l ALOGPS logp -2.4 ChemAxon pka_strongest_acidic 3.21 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (2S,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolane-2-carboxylic acid ChemAxon average_mass 194.1394 ChemAxon mono_mass 194.042652674 ChemAxon smiles [H][C@]1(O)[C@]([H])(O)C(O)(CO)O[C@]1([H])C(O)=O ChemAxon formula C6H10O7 ChemAxon inchi InChI=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/s1 ChemAxon inchikey PTCIWUZVDIQTOW-XDJBDKDSSA-N ChemAxon polar_surface_area 127.45 ChemAxon refractivity 36.23 ChemAxon polarizability 16.4 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Pentose and glucuronate interconversions ec00040 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 Specdb::CMs 1083534 Specdb::EiMs 3211 Specdb::NmrOneD 257948 Specdb::NmrOneD 257949 Specdb::NmrOneD 257950 Specdb::NmrOneD 257951 Specdb::NmrOneD 257952 Specdb::NmrOneD 257953 Specdb::NmrOneD 257954 Specdb::NmrOneD 257955 Specdb::NmrOneD 257956 Specdb::NmrOneD 257957 Specdb::NmrOneD 257958 Specdb::NmrOneD 257959 Specdb::NmrOneD 257960 Specdb::NmrOneD 257961 Specdb::NmrOneD 257962 Specdb::NmrOneD 257963 Specdb::NmrOneD 257964 Specdb::NmrOneD 257965 Specdb::NmrOneD 257966 Specdb::NmrOneD 257967 Specdb::MsMs 29090 Specdb::MsMs 29091 Specdb::MsMs 29092 Specdb::MsMs 35648 Specdb::MsMs 35649 Specdb::MsMs 35650 439343 388470 C00905 16849 FRUCTURONATE 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 Nguyen, 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. 18171028 Uronate isomerase P0A8G3 UXAC_ECOLI uxaC http://ecmdb.ca/proteins/P0A8G3.xml D-mannonate oxidoreductase P39160 UXUB_ECOLI uxuB http://ecmdb.ca/proteins/P39160.xml Starvation-sensing protein RspB P38105 RSPB_ECOLI rspB http://ecmdb.ca/proteins/P38105.xml High-affinity gluconate transporter P0AC94 GNTP_ECOLI gntP http://ecmdb.ca/proteins/P0AC94.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-Glucuronic acid <> D-Fructuronate R01482 GLUCUROISOM-RXN D-Mannonate + NAD <> D-Fructuronate + Hydrogen ion + NADH R02454 MANNONOXIDOREDUCT-RXN D-Glucuronic acid > D-Fructuronate D-Mannonate + NAD > D-Fructuronate + NADH L-Gulonate + NAD <> D-Fructuronate + NADH + Hydrogen ion R10848 aldehydo-D-glucuronate > D-Fructuronate PW_R003058 D-Fructuronate + NADH + Hydrogen ion > NAD + D-altronate PW_R003059