2.0 2012-05-31 14:07:26 -0600 2015-06-03 15:54:50 -0600 ECMDB04178 M2MDB000653 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 carbohydrates to cells 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; EC 2.7.1.11] in glycolysis and will increase transcription of the genes for the enzymes of lipogenesis, the hexose monophosphate shunt, and glycolysis, all of which are required for the de novo synthesis of fat. (PMID 12721358) 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 X5P Xu-5-P Xylulose 5-phosphate Xylulose 5-phosphoric acid Xylulose-P Xylulose-phosphate Xylulose-phosphoric acid C5H11O8P 230.1098 230.01915384 {[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid ribulose-5-phosphate 4212-65-1 OCC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/t4-,5-/m1/s1 FNZLKVNUWIIPSJ-RFZPGFLSSA-N Solid Cytosol logp -1.81 ALOGPS logs -0.95 ALOGPS solubility 2.61e+01 g/l ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 1.48 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac {[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid ChemAxon average_mass 230.1098 ChemAxon mono_mass 230.01915384 ChemAxon smiles OCC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O ChemAxon formula C5H11O8P ChemAxon inchi InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/t4-,5-/m1/s1 ChemAxon inchikey FNZLKVNUWIIPSJ-RFZPGFLSSA-N ChemAxon polar_surface_area 144.52 ChemAxon refractivity 42.47 ChemAxon polarizability 18.05 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Carbon fixation in photosynthetic organisms ec00710 Ascorbate and aldarate metabolism ec00053 Methane metabolism ec00680 Pentose and glucuronate interconversions ec00040 Biosynthesis of ansamycins ec01051 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 Pentose Phosphate PW000893 Metabolic L-arabinose Degradation I Because L-arabinose enters E. coli either by a low-affinity proton-driven transporter (AraE) or a high-affinity ATP-driven system (AraFGH), its first intracellular form is unphosphorylated. Then an isomerase and a kinase convert it to L-ribulose-5-phosphate. An epimerase converts L-ribulose-5-phosphate to D-xylulose-5-phosphate, an intermediate of the pentose phosphate pathway, which thereby flows through the pathways of central metabolism to satisfy the cell's need for precursor metabolites, reducing power, and metabolic energy. (EcoCyc) PW002103 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 Xylose Degradation I D-xylose, which can serve as a total source of carbon and energy for Escherichia coli K-12 substr. MG1655, enters the cell either through a low-affinity, proton-motive force-driven or a high-affinity, ATP-driven (ABC) transport system, so it is not phosphorylated during entry. Once inside the cell, an isomerase converts it to D-xylulose and subsequently a kinase converts it to D-xylulose 5-phosphate, an intermediate of the pentose phosphate pathway. Hence it flows through the pathways of central metabolism to satisfy the cell's need for precursor metabolites, reducing power, and metabolic energy. (EcoCyc) PW002105 Metabolic L-ascorbate degradation II (bacterial, aerobic) PWY-6961 pentose phosphate pathway (non-oxidative branch) NONOXIPENT-PWY L-ascorbate degradation I (bacterial, anaerobic) PWY0-301 L-lyxose degradation LYXMET-PWY L-arabinose degradation I ARABCAT-PWY xylose degradation I XYLCAT-PWY Specdb::CMs 3396 Specdb::CMs 37815 Specdb::CMs 133240 Specdb::CMs 140974 Specdb::CMs 1080560 Specdb::CMs 1080562 Specdb::CMs 1080563 Specdb::CMs 1080565 Specdb::CMs 1080567 Specdb::CMs 1080569 Specdb::CMs 1080571 Specdb::CMs 1080573 Specdb::CMs 1080574 Specdb::CMs 1080576 Specdb::CMs 1080578 Specdb::CMs 1080580 Specdb::CMs 1080582 Specdb::CMs 1080584 Specdb::CMs 1080585 Specdb::CMs 1080587 Specdb::CMs 1080589 Specdb::CMs 1080591 Specdb::CMs 1080592 Specdb::CMs 1080594 Specdb::CMs 1080596 Specdb::NmrOneD 247448 Specdb::NmrOneD 247449 Specdb::NmrOneD 247450 Specdb::NmrOneD 247451 Specdb::NmrOneD 247452 Specdb::NmrOneD 247453 Specdb::NmrOneD 247454 Specdb::NmrOneD 247455 Specdb::NmrOneD 247456 Specdb::NmrOneD 247457 Specdb::NmrOneD 247458 Specdb::NmrOneD 247459 Specdb::NmrOneD 247460 Specdb::NmrOneD 247461 Specdb::NmrOneD 247462 Specdb::NmrOneD 247463 Specdb::NmrOneD 247464 Specdb::NmrOneD 247465 Specdb::NmrOneD 247466 Specdb::NmrOneD 247467 Specdb::MsMs 24884 Specdb::MsMs 24885 Specdb::MsMs 24886 Specdb::MsMs 31442 Specdb::MsMs 31443 Specdb::MsMs 31444 Specdb::MsMs 1471362 Specdb::MsMs 1471363 Specdb::MsMs 1471364 Specdb::MsMs 1471365 Specdb::MsMs 1471366 Specdb::MsMs 1471367 Specdb::MsMs 1471368 Specdb::MsMs 1471369 Specdb::MsMs 1471370 Specdb::MsMs 1471371 Specdb::MsMs 1471372 Specdb::MsMs 1471373 Specdb::MsMs 1471374 Specdb::MsMs 1471375 Specdb::MsMs 1471376 Specdb::MsMs 1471377 Specdb::MsMs 1471378 Specdb::MsMs 1471428 Specdb::MsMs 1471429 HMDB00868 850 388330 C00231 16332 XYLULOSE-5-PHOSPHATE 5SP Xylulose 5-phosphate Keseler, I. 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L-ribulose-5-phosphate 4-epimerase P08203 ARAD_ECOLI araD http://ecmdb.ca/proteins/P08203.xml Ribulokinase P08204 ARAB_ECOLI araB http://ecmdb.ca/proteins/P08204.xml Xylulose kinase P09099 XYLB_ECOLI xylB http://ecmdb.ca/proteins/P09099.xml Ribulose-phosphate 3-epimerase P0AG07 RPE_ECOLI rpe http://ecmdb.ca/proteins/P0AG07.xml Transketolase 1 P27302 TKT1_ECOLI tktA http://ecmdb.ca/proteins/P27302.xml Transketolase 2 P33570 TKT2_ECOLI tktB http://ecmdb.ca/proteins/P33570.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 L-ribulose-5-phosphate 4-epimerase sgbE P37680 SGBE_ECOLI sgbE http://ecmdb.ca/proteins/P37680.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 L-ribulose-5-phosphate 4-epimerase ulaF P39306 ULAF_ECOLI ulaF http://ecmdb.ca/proteins/P39306.xml Protein sgcE P39362 SGCE_ECOLI sgcE http://ecmdb.ca/proteins/P39362.xml Adenosine triphosphate + D-Xylulose <> ADP + Hydrogen ion + Xylulose 5-phosphate R01639 XYLULOKIN-RXN D-Ribose-5-phosphate + Xylulose 5-phosphate <> D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate 1TRANSKETO-RXN D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate R01067 2TRANSKETO-RXN L-Ribulose 5-phosphate <> Xylulose 5-phosphate R05850 RIBULPEPIM-RXN D-Ribulose 5-phosphate <> Xylulose 5-phosphate R01529 RIBULP3EPIM-RXN Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate R01067 D-Ribulose 5-phosphate <> Xylulose 5-phosphate R01529 Adenosine triphosphate + D-Xylulose <> ADP + Xylulose 5-phosphate R01639 Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate <> D-Ribose-5-phosphate + Xylulose 5-phosphate R01641 beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate R01830 D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Ribose-5-phosphate + Xylulose 5-phosphate 1TRANSKETO-RXN D-Xylulose + Adenosine triphosphate > Hydrogen ion + Xylulose 5-phosphate + ADP XYLULOKIN-RXN L-Ribulose 5-phosphate > Xylulose 5-phosphate D-Ribulose 5-phosphate > Xylulose 5-phosphate Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate > D-Ribose-5-phosphate + Xylulose 5-phosphate Adenosine triphosphate + D-Xylulose > ADP + Xylulose 5-phosphate D-Ribulose 5-phosphate <> Xylulose 5-phosphate + Xylulose 5-phosphate PW_R003341 Xylulose 5-phosphate + D-Ribose-5-phosphate + Xylulose 5-phosphate <> D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate PW_R003345 L-Threo-2-pentulose + Adenosine triphosphate + L-Threo-2-pentulose > Xylulose 5-phosphate + Adenosine diphosphate + Xylulose 5-phosphate + ADP PW_R003849 3-keto-L-gulonate 6-phosphate + Hydrogen ion + 3-Keto-L-gulonate 6-phosphate > Xylulose 5-phosphate + Carbon dioxide + Xylulose 5-phosphate PW_R002703 2,3-Diketo-L-gulonate + Hydrogen ion + 2,3-Diketo-L-gulonate > Carbon dioxide + Xylulose 5-phosphate + Xylulose 5-phosphate PW_R002704 Xylulose 5-phosphate + Xylulose 5-phosphate > L-ribulose 5-phosphate + L-ribulose 5-phosphate PW_R002706 L-ribulose 5-phosphate + L-ribulose 5-phosphate > Xylulose 5-phosphate + Xylulose 5-phosphate PW_R002707 L-Threo-2-pentulose + Adenosine triphosphate > Xylulose 5-phosphate + ADP + Hydrogen ion PW_R006135 L-ribulose 5-phosphate <> Xylulose 5-phosphate PW_R006127 D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate D-Ribulose 5-phosphate <> Xylulose 5-phosphate D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate 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