2.0 2012-05-31 14:31:10 -0600 2015-09-18 15:17:18 -0600 ECMDB20169 M2MDB001016 L-Xylulose 5-phosphate )Xylulose 5-phosphate (Xu-5-P) is a metabolite of the hexose monophosphate pathway that activates protein phosphatase 2A to mediate the acute effects of carbohydrate feeding on the glycolytic pathway, as well as the coordinate long-term control of the enzymes required for fatty acid and triglyceride synthesis. Xu-5-P is the signal for the coordinated control of lipogenesis. Feeding carbohydrate causes levels of glucose, Glucose-6-phosphate (Glc-6-P), and Fructose-6-phosphate (Fru-6-P) to rise. Elevation of Fru-6-P leads to elevation of Xu-5-P in reactions catalyzed by the near-equilibrium isomerases of the nonoxidative portion of the hexose monophosphate pathway (ribulose 5-phosphate (Ru5P) epimerase [EC 5.1.3.1], ribose 5-phosphate (Rib5P) isomerase [EC 5.3.1.6], transaldolase [EC 2.2.1.2], and transketolase [EC 2.2.1.1]). The elevation of Xu-5-P is the coordinating signal that both acutely activates phosphofructokinase [PFK 2-Pentulose, 5-(dihydrogen phosphate) 2-Pentulose, 5-(dihydrogen phosphoric acid) D-Ribulose-5-P D-Ribulose-5-phosphate D-Ribulose-5-phosphoric acid D-Xylulose 5-phosphate D-Xylulose 5-phosphoric acid D-Xylulose 5-PO4 D-Xylulose-5-P D-Xylulose-5-phosphate D-Xylulose-5-phosphoric acid L-RIBULOSE-5-P L-Ribulose-5-phosphate L-Ribulose-5-phosphoric acid L-X5P L-Xylulose 5-phosphoric acid L-XYLULOSE-5-P L-Xylulose-5-phosphate L-Xylulose-5-phosphoric acid Ribulose-5-P Ribulose-5-Phosphate Ribulose-5-phosphoric acid RIBULOSE-5P Xu-5-P Xylulose 5-phosphate Xylulose 5-phosphoric acid Xylulose-5-P Xylulose-5-phosphate Xylulose-5-phosphoric acid Xylulose-p Xylulose-phosphate Xylulose-phosphoric acid [(2R,3R)-2,3,5-trihydroxy-4-oxopentyl] dihydrogen phosphate [(2R,3R)-2,3,5-Trihydroxy-4-oxopentyl] dihydrogen phosphoric acid C7H13O6P 224.15 224.046072296 1-hydroxy-3,4-dimethyl-5-(phosphonatooxy)pentan-2-one 1-hydroxy-3,4-dimethyl-5-(phosphonatooxy)pentan-2-one 60802-29-1 CC(COP([O-])([O-])=O)C(C)C(=O)CO InChI=1S/C7H15O6P/c1-5(4-13-14(10,11)12)6(2)7(9)3-8/h5-6,8H,3-4H2,1-2H3,(H2,10,11,12)/p-2 GOBYCGYLQSIFMQ-UHFFFAOYSA-L Solid Cytosol logp -0.42 ALOGPS logs -0.83 ALOGPS solubility 3.85e+01 g/l ALOGPS logp -0.22 ChemAxon pka_strongest_acidic 1.81 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac 1-hydroxy-3,4-dimethyl-5-(phosphonatooxy)pentan-2-one ChemAxon average_mass 224.15 ChemAxon mono_mass 224.046072296 ChemAxon smiles CC(COP([O-])([O-])=O)C(C)C(=O)CO ChemAxon formula C7H13O6P ChemAxon inchi InChI=1S/C7H15O6P/c1-5(4-13-14(10,11)12)6(2)7(9)3-8/h5-6,8H,3-4H2,1-2H3,(H2,10,11,12)/p-2 ChemAxon inchikey GOBYCGYLQSIFMQ-UHFFFAOYSA-L ChemAxon polar_surface_area 109.72 ChemAxon refractivity 46.73 ChemAxon polarizability 19.62 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 1 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon Ascorbate and aldarate metabolism ec00053 Pentose and glucuronate interconversions ec00040 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Ascorbate metabolism E. coli is able to utilize L-ascorbate (vitamin C) as the sole source of carbon under anaerobic and aerobic conditions. Ascorbic acid in the cytoplasm is processed through a spontaneous reaction with a hydrogen ion and hydrogen peroxide, producing water, dehydroascorbic acid and ascorbic acid. Dehydroascorbic acid reacts with water spontaneously producing an isomer, dehydroascorbate (bicyclic form). The compound then loses a hydrogen ion resulting in a 2,3-Diketo-L-gulonate. This compound is then reduced through a NADH dependent 2,3 diketo-L-gulonate reductase, releasing a NAD and 3-Dehydro-L-gulonate.This compound is phosphorylated through an ATP mediated L-xylulose/3-keto-L-gulonate kinase resulting in an ADP, hydrogen ion and a 3-Keto-L-gulonate 6 phosphate. L-ascorbate can also be imported and converted to L-ascorbate-6-phosphate by the L-ascorbate PTS transporter. L-ascorbate-6-phosphate reacts with a probable L-ascorbate-6-phosphate lactonase ulaG, resulting in a 3-keto-L-gulonate 6-phosphate. The compound 3-keto-L-gulonate 6-phosphate can be processed aerobically or anaerobically. Aerobic: 3-keto-L-gulonate 6-phosphate is decarboxylated by a 3-keto-L-gulonate-6-phosphate decarboxylase ulaD, releasing carbon dioxide and L-xylulose-5-phosphate. This compound in turn is changed into an isomer by L-ribulose-5-phosphate 3-epimerase ulaE, resulting in L-ribulose 5-phosphate. This compound again changes into a different isomer through a L-ribulose-5-phosphate 4-epimerase ulaF resulting in Xylulose 5-phosphate. This compound can then be part of the pentose phosphate pathway. Anaerobic: 3-keto-L-gulonate 6-phosphate is decarboxylated by 3-keto-L-gulonate 6-phosphate decarboxylase sgbH, releasing carbon dioxide and L-xylulose-5-phosphate. This compound in turn is changed into an isomer by predicted L-xylulose 5-phosphate 3-epimerase, resulting in L-ribulose 5-phosphate. This compound again changes into a different isomer through a L-ribulose-5-phosphate 4-epimerase resulting in Xylulose 5-phosphate. This compound can then be part of the pentose phosphate pathway. Expression of the ula regulon is regulated by the L-ascorbate 6-phosphate-binding repressor UlaR and by cAMP-CRP. Under aerobic conditions, metabolism of L-ascorbate is hindered by the special reactivity and toxicity of this compound in the presence of oxygen. PW000793 Metabolic L-lyxose Degradation L-lyxose is an uncommon sugar in nature, and wild-type E. coli can not utilize it as a sole source of carbon and energy. However, mutations can arise that allow E. coli to metabolize L-lyxose through the use of enzymes of the rhamnose, arabinose and 2,3-diketo-L-gulonate systems. L-lyxose enters the cell through the rhaT-encoded rhamnose transporter. It is then isomerized to L-xylulose by L-rhamnose isomerase. Two types of mutations then allow further utilization of L-xylulose. Not shown here, a mutated from of L-rhamnulose kinase can phosphorylate L-xylulose, yielding L-xylulose-1-phosphate. Further metabolism to dihydroxyacetone phosphate and glycolate occurs through the rhamnulose-1-phosphate aldolase and aldehyde dehydrogenase A, NAD-linked enzymes. These products can enter glycolate degradation and glycolysis. As shown here, L-xylulose can be phosphorylated by L-xylulose kinase in a mutant in which YiaJ, the repressor for the yiaKLMNO-lyxK-sgbHUE operon, has been disrupted. L-xylulose-5-phosphate is then further metabolized by predicted L-xylulose 5-phosphate 3-epimerase (so far only a predicted function) and either of two L-ribulose 5-phosphate 4-epimerases (SgbE or AraD) to D-xylulose-5-phosphate, which then enters the pentose phosphate pathway (non-oxidative branch). The enzymes of L-rhamnose degradation I and L-arabinose degradation I are inducible by L-lyxose as well. (EcoCyc) PW002100 Metabolic L-ascorbate degradation II (bacterial, aerobic) PWY-6961 L-ascorbate degradation I (bacterial, anaerobic) PWY0-301 L-lyxose degradation LYXMET-PWY Specdb::NmrOneD 270998 Specdb::NmrOneD 270999 Specdb::NmrOneD 271000 Specdb::NmrOneD 271001 Specdb::NmrOneD 271002 Specdb::NmrOneD 271003 Specdb::NmrOneD 271004 Specdb::NmrOneD 271005 Specdb::NmrOneD 271006 Specdb::NmrOneD 271007 Specdb::NmrOneD 271008 Specdb::NmrOneD 271009 Specdb::NmrOneD 271010 Specdb::NmrOneD 271011 Specdb::NmrOneD 271012 Specdb::NmrOneD 271013 Specdb::NmrOneD 271014 Specdb::NmrOneD 271015 Specdb::NmrOneD 271016 Specdb::NmrOneD 271017 850 827 C03291 16593 L-XYLULOSE-5-P 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 Winder, 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. 18331064 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Ribulokinase P08204 ARAB_ECOLI araB http://ecmdb.ca/proteins/P08204.xml L-xylulose/3-keto-L-gulonate kinase P37677 LYXK_ECOLI lyx http://ecmdb.ca/proteins/P37677.xml 3-keto-L-gulonate-6-phosphate decarboxylase sgbH P37678 SGBH_ECOLI sgbH http://ecmdb.ca/proteins/P37678.xml 3-keto-L-gulonate-6-phosphate decarboxylase ulaD P39304 ULAD_ECOLI ulaD http://ecmdb.ca/proteins/P39304.xml L-ribulose-5-phosphate 3-epimerase ulaE P39305 ULAE_ECOLI ulaE http://ecmdb.ca/proteins/P39305.xml predicted L-xylulose 5-phosphate 3-epimerase P37679 yiaR http://ecmdb.ca/proteins/P37679.xml Adenosine triphosphate + L-Threo-2-pentulose <> ADP + Hydrogen ion + L-Xylulose 5-phosphate R01901 3-Dehydro-L-gulonate 6-phosphate + Hydrogen ion <> Carbon dioxide + L-Xylulose 5-phosphate R07125 RXN0-705 L-Xylulose 5-phosphate <> L-Ribulose 5-phosphate R03244 LXULRU5P-RXN Adenosine triphosphate + L-Threo-2-pentulose <> ADP + L-Xylulose 5-phosphate R01901 L-Ribulose 5-phosphate <> L-Xylulose 5-phosphate R03244 LXULRU5P-RXN L-Ribulose 5-phosphate < L-Xylulose 5-phosphate LXULRU5P-RXN L-xylulose + Adenosine triphosphate > Hydrogen ion + L-Xylulose 5-phosphate + ADP LYXK-RXN Hydrogen ion + 3-Dehydro-L-gulonate 6-phosphate > L-Xylulose 5-phosphate + Carbon dioxide RXN0-705 Adenosine triphosphate + L-Threo-2-pentulose > ADP + L-Xylulose 5-phosphate 3-Dehydro-L-gulonate 6-phosphate > L-Xylulose 5-phosphate + Carbon dioxide L-Ribulose 5-phosphate > L-Xylulose 5-phosphate 3-keto-L-gulonate 6-phosphate + Hydrogen ion + 3-Keto-L-gulonate 6-phosphate > L-xylulose -5-phosphate + Carbon dioxide + L-Xylulose 5-phosphate PW_R002712 3-keto-L-gulonate 6-phosphate + 3-Keto-L-gulonate 6-phosphate > L-xylulose -5-phosphate + L-Xylulose 5-phosphate PW_R002711 L-xylulose -5-phosphate + L-Xylulose 5-phosphate > L-ribulose 5-phosphate + L-ribulose 5-phosphate PW_R002710 L-Threo-2-pentulose + Adenosine triphosphate > L-Xylulose 5-phosphate + ADP + Hydrogen ion PW_R006125 L-Xylulose 5-phosphate > L-ribulose 5-phosphate PW_R006126 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Shake flask and filter culture 1020.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 4080000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Shake flask and filter culture 686.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 2744000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 1320.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 5280000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621