2.0 2012-05-31 14:31:03 -0600 2015-06-03 17:19:26 -0600 ECMDB20167 M2MDB001014 L-Ribulose 5-phosphate L-ribulose 5-phosphate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. In Escherichia coli, RpiA catalyzes the interconversion of ribose-5-phosphate and ribulose-5-phosphate and is a key enzyme in the pentose phosphate pathway. (PMID 12182339) Interconversion of D-ribose-5-phosphate (R5P) and D-ribulose-5-phosphate is an important step in the pentose phosphate pathway. (PMID 18640127) A key player in LPS synthesis is the enzyme D-arabinose-5-phosphate isomerase (API), which catalyzes the reversible isomerization of D-ribulose-5-phosphate to D-arabinose-5-phosphate, a precursor of 3-deoxy-D-manno-octulosonate that is an essential residue of the LPS inner core. (PMID 20954237) Dihydroxybutanone phosphate synthase (DS) catalyzes a commitment step in riboflavin biosynthesis where ribulose 5-phosphate is converted to dihydroxybutanone phosphate and formate. (PMID 11053863) Ribose-5-phosphate isomerase A (RpiA) plays an important role in interconverting between ribose-5-phosphate (R5P) and ribulose-5-phosphate in the pentose phosphate pathway and the Calvin cycle. (PMID 19214439) 5-O-Phosphono-L-erythro-pent-2-ulose 5-O-Phosphono-L-ribulose L-Erythro-pent-2-ulose 5-(dihydrogen phosphate) L-erythro-Pent-2-ulose 5-(dihydrogen phosphoric acid) L-Ribulose 5-(dihydrogen phosphate) L-Ribulose 5-(dihydrogen phosphoric acid) L-Ribulose 5-phosphoric acid L-Ribulose-5-P Ribulose 5-phosphate Ribulose 5-phosphoric acid Ribulose-5-P Ribulose-5-phosphate Ribulose-5-phosphoric acid C5H11O8P 230.1098 230.01915384 {[(2S,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid L-ribulose 5-phosphate 2922-69-2 [H][C@](O)(COP(O)(O)=O)[C@]([H])(O)C(=O)CO 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+/m0/s1 FNZLKVNUWIIPSJ-CRCLSJGQSA-N 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 {[(2S,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid ChemAxon average_mass 230.1098 ChemAxon mono_mass 230.01915384 ChemAxon smiles [H][C@](O)(COP(O)(O)=O)[C@]([H])(O)C(=O)CO 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+/m0/s1 ChemAxon inchikey FNZLKVNUWIIPSJ-CRCLSJGQSA-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 Ascorbate and aldarate metabolism ec00053 Pentose and glucuronate interconversions ec00040 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 L-ascorbate degradation II (bacterial, aerobic) PWY-6961 L-ascorbate degradation I (bacterial, anaerobic) PWY0-301 L-lyxose degradation LYXMET-PWY L-arabinose degradation I ARABCAT-PWY Specdb::CMs 1083264 Specdb::NmrOneD 314401 Specdb::NmrOneD 314402 Specdb::NmrOneD 314403 Specdb::NmrOneD 314404 Specdb::NmrOneD 314405 Specdb::NmrOneD 314406 Specdb::NmrOneD 314407 Specdb::NmrOneD 314408 Specdb::NmrOneD 314409 Specdb::NmrOneD 314410 Specdb::NmrOneD 314411 Specdb::NmrOneD 314412 Specdb::NmrOneD 314413 Specdb::NmrOneD 314414 Specdb::NmrOneD 314415 Specdb::NmrOneD 314416 Specdb::NmrOneD 314417 Specdb::NmrOneD 314418 Specdb::NmrOneD 314419 Specdb::NmrOneD 314420 Specdb::MsMs 28211 Specdb::MsMs 28212 Specdb::MsMs 28213 Specdb::MsMs 34769 Specdb::MsMs 34770 Specdb::MsMs 34771 439399 388516 C01101 17666 L-RIBULOSE-5-P HMS 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 Park, C., Park, C., Lee, Y., Lee, S.Y., Oh, H.B., Lee, J. (2011) Determination of the Intracellular Concentration of Metabolites in Escherichia coli Collected during the Exponential and Stationary Growth Phases using Liquid Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 32: 524-530. Gourlay, L. J., Sommaruga, S., Nardini, M., Sperandeo, P., Deho, G., Polissi, A., Bolognesi, M. (2010). "Probing the active site of the sugar isomerase domain from E. coli arabinose-5-phosphate isomerase via X-ray crystallography." Protein Sci 19:2430-2439. 20954237 Roos, A. K., Mariano, S., Kowalinski, E., Salmon, L., Mowbray, S. L. (2008). "D-ribose-5-phosphate isomerase B from Escherichia coli is also a functional D-allose-6-phosphate isomerase, while the Mycobacterium tuberculosis enzyme is not." J Mol Biol 382:667-679. 18640127 Lohrke, S. M., Dery, P. D., Li, W., Reedy, R., Kobayashi, D. Y., Roberts, D. R. (2002). "Mutation of rpiA in Enterobacter cloacae decreases seed and root colonization and biocontrol of damping-off caused by Pythium ultimum on cucumber." Mol Plant Microbe Interact 15:817-825. 12182339 Liao, D. I., Viitanen, P. V., Jordan, D. B. (2000). "Cloning, expression, purification and crystallization of dihydroxybutanone phosphate synthase from Magnaporthe grisea." Acta Crystallogr D Biol Crystallogr 56:1495-1497. 11053863 Kim, T. G., Kwon, T. H., Min, K., Dong, M. S., Park, Y. I., Ban, C. (2009). "Crystal structures of substrate and inhibitor complexes of ribose 5-phosphate isomerase A from Vibrio vulnificus YJ016." Mol Cells 27:99-103. 19214439 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 L-ribulose-5-phosphate 4-epimerase sgbE P37680 SGBE_ECOLI sgbE http://ecmdb.ca/proteins/P37680.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 predicted L-xylulose 5-phosphate 3-epimerase P37679 yiaR http://ecmdb.ca/proteins/P37679.xml L-Ribulose 5-phosphate <> Xylulose 5-phosphate R05850 RIBULPEPIM-RXN Adenosine triphosphate + L-Ribulose > ADP + Hydrogen ion + L-Ribulose 5-phosphate R02439 RXN0-5116 L-Xylulose 5-phosphate <> L-Ribulose 5-phosphate R03244 LXULRU5P-RXN Adenosine triphosphate + L-Ribulose <> ADP + L-Ribulose 5-phosphate R02439 RXN0-5116 L-Ribulose 5-phosphate <> L-Xylulose 5-phosphate R03244 LXULRU5P-RXN L-Ribulose 5-phosphate < L-Xylulose 5-phosphate LXULRU5P-RXN L-Ribulose 5-phosphate > Xylulose 5-phosphate L-Ribulose 5-phosphate > L-Xylulose 5-phosphate Adenosine triphosphate + L-Ribulose + D-Ribulose <> ADP + L-Ribulose 5-phosphate + D-Ribulose 5-phosphate R01526 R02439 4.0 g/L Na2SO4; 5.36 g/L (NH4)2SO4; 1.0 g/L NH4Cl; 7.3 g/L K2HPO4; 1.8 g/L NaH2PO4 H2O; 12.0 g/L (NH4)2-H-citrate; 4.0 mL/L MgSO4 (1 M); 6.0 mL/L trace element solution; 0.02 g/L thiamine, 20 g/L glucose Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h 2.3 uM 0.0 37 oC W3110 Mid Log Phase 9200 0 Park, C., Park, C., Lee, Y., Lee, S.Y., Oh, H.B., Lee, J. (2011) Determination of the Intracellular Concentration of Metabolites in Escherichia coli Collected during the Exponential and Stationary Growth Phases using Liquid Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 32: 524-530. 4.0 g/L Na2SO4; 5.36 g/L (NH4)2SO4; 1.0 g/L NH4Cl; 7.3 g/L K2HPO4; 1.8 g/L NaH2PO4 H2O; 12.0 g/L (NH4)2-H-citrate; 4.0 mL/L MgSO4 (1 M); 6.0 mL/L trace element solution; 0.02 g/L thiamine, 20 g/L glucose Bioreactor, pH controlled, aerated 2.2 uM 0.0 37 oC W3110 Stationary Phase 8800 0 Park, C., Park, C., Lee, Y., Lee, S.Y., Oh, H.B., Lee, J. (2011) Determination of the Intracellular Concentration of Metabolites in Escherichia coli Collected during the Exponential and Stationary Growth Phases using Liquid Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 32: 524-530.