2.02012-05-31 14:28:42 -06002015-06-03 17:19:21 -0600ECMDB20123M2MDB000971beta-D-Fructose 1,6-bisphosphateBeta-D-fructose 1,6-bisphosphate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. The hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate is a key reaction of carbohydrate metabolism. (PMID 3008716) Fructose-1,6-bisphosphate (F-1,6-P2) is an allosteric activator of two key enzymes of glycolysis: phosphofructokinase and pyruvate kinase. (PMID 18025560) In gluconeogenesis, fructose 6-phosphate is formed from fructose 1,6-bisphosphate, and if fructose 1,6-bisphosphate were reformed by the phosphofructokinase reaction there would be a "gluconeogenic futile cycle". (PMID 6217196) Fructose-1,6-bisphosphate (FBP) aldolase is an essential glycolytic enzyme that reversibly cleaves its ketohexose substrate into triose phosphates. (PMID 14699122) Fructose 1-phosphate is a metabolite that plays a regulatory role in metabolism and is best measured using an assay based on its conversion to fructose 1,6-bisphosphate by a bacterial fructose-1-phosphate kinase (Fru1PK). (PMID 10833389) For growth, the assimilated fructose is sequentially phosphorylated by ATP and (i) manno(fructo)kinase, to form fructose 6-phosphate, and (ii) phosphofructokinase, to form fructose 1,6-bisphosphate, which is a member of central routes of glycolysis and gluconeogenesis. (PMID 17159144)β-D-fructose-1,6-diphosphateβ-D-fructose-1,6-diphosphoric acid1,6-Di-O-phosphono-b-D-fructofuranose1,6-Di-O-phosphono-beta-D-fructofuranose1,6-Di-O-phosphono-β-D-fructofuranose6055-82-9 (Calcium[1:2] salt)b Fructose 1,6-diphosphateb Fructose 1,6-diphosphoric acidb-D-Fructofuranose 1,6-bis(dihydrogen phosphate)b-D-Fructofuranose 1,6-bis(dihydrogen phosphoric acid)b-D-Fructofuranose 1,6-bisphosphateb-D-Fructofuranose 1,6-bisphosphoric acidb-D-Fructofuranose, 1,6-bis(dihydrogen phosphate)b-D-Fructofuranose, 1,6-bis(dihydrogen phosphoric acid)b-D-Fructose 1,6-bisphosphateb-D-Fructose 1,6-bisphosphoric acidb-D-Fructose-1,6-diphosphateb-D-Fructose-1,6-diphosphoric acidBeta Fructose 1,6-diphosphatebeta Fructose 1,6-diphosphoric acidBeta-D-Fructofuranose 1,6-bis(dihydrogen phosphate)beta-D-Fructofuranose 1,6-bis(dihydrogen phosphoric acid)Beta-D-Fructofuranose 1,6-bisphosphatebeta-D-Fructofuranose 1,6-bisphosphoric acidBeta-D-Fructofuranose, 1,6-bis(dihydrogen phosphate)beta-D-Fructofuranose, 1,6-bis(dihydrogen phosphoric acid)beta-D-Fructose 1,6-bisphosphoric acidBeta-D-Fructose-1,6-diphosphatebeta-D-Fructose-1,6-diphosphoric acidBFPD-Arabino-2-Hexulose-1,6-bis(dihydrogenphosphat)D-Fructofuranose, 1,6-bis(dihydrogen phosphate)D-Fructofuranose, 1,6-bis(dihydrogen phosphoric acid)D-Fructose 1,6-bis(dihydrogen phosphate)D-Fructose 1,6-bis(dihydrogen phosphoric acid)D-Fructose, 1,6-bis(dihydrogen phosphate)D-Fructose, 1,6-bis(dihydrogen phosphoric acid)D-Fructose-1,6-bis(dihydrogenphosphat)D-Fructose-1,6-bisphosphateD-Fructose-1,6-bisphosphoric acidD-Fructose-1,6-diphosphateD-Fructose-1,6-diphosphoric acidFBPFructose 1,6-bisphosphateFructose 1,6-bisphosphoric acidFructose 1,6-diphosphateFructose 1,6-diphosphoric acidFructose-1,6-biphosphateFructose-1,6-biphosphoric acidFructose-1,6-bisphosphateFructose-1,6-bisphosphoric acidFructose-1,6-diphosphateFructose-1,6-diphosphoric acidHarden-young-esterβ Fructose 1,6-diphosphateβ Fructose 1,6-diphosphoric acidβ-D-Fructofuranose 1,6-bis(dihydrogen phosphate)β-D-Fructofuranose 1,6-bis(dihydrogen phosphoric acid)β-D-Fructofuranose 1,6-bisphosphateβ-D-Fructofuranose 1,6-bisphosphoric acidβ-D-Fructofuranose, 1,6-bis(dihydrogen phosphate)β-D-Fructofuranose, 1,6-bis(dihydrogen phosphoric acid)β-D-Fructose 1,6-bisphosphateβ-D-Fructose 1,6-bisphosphoric acidβ-D-Fructose-1,6-diphosphateβ-D-Fructose-1,6-diphosphoric acidC6H14O12P2340.1157339.996048936{[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid125740-83-2O[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=OInChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6-/m1/s1RNBGYGVWRKECFJ-ARQDHWQXSA-NCytoplasmPeriplasmlogp-1.51logs-1.33solubility1.61e+01 g/llogp-3pka_strongest_acidic0.89pka_strongest_basic-3.7iupac{[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acidaverage_mass340.1157mono_mass339.996048936smilesO[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=OformulaC6H14O12P2inchiInChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6-/m1/s1inchikeyRNBGYGVWRKECFJ-ARQDHWQXSA-Npolar_surface_area203.44refractivity58.11polarizability25.7rotatable_bond_count6acceptor_count10donor_count7physiological_charge-4formal_charge0Pentose phosphate pathwayec00030Glycolysis / Gluconeogenesisec00010Fructose and mannose metabolismec00051Microbial metabolism in diverse environmentsec01120gluconeogenesis IGLUCONEO-PWYglycolysis IGLYCOLYSISfructose degradationPWY0-1314Specdb::CMs2061Specdb::CMs2080Specdb::CMs2081Specdb::CMs36588Specdb::CMs48214Specdb::CMs174473Specdb::NmrOneD8462Specdb::NmrOneD8463Specdb::NmrOneD8464Specdb::NmrOneD8465Specdb::NmrOneD8466Specdb::NmrOneD8467Specdb::NmrOneD8468Specdb::NmrOneD8469Specdb::NmrOneD8470Specdb::NmrOneD8471Specdb::NmrOneD8472Specdb::NmrOneD8473Specdb::NmrOneD8474Specdb::NmrOneD8475Specdb::NmrOneD8476Specdb::NmrOneD8477Specdb::NmrOneD8478Specdb::NmrOneD8479Specdb::NmrOneD8480Specdb::NmrOneD8481Specdb::MsMs25193Specdb::MsMs25194Specdb::MsMs25195Specdb::MsMs31751Specdb::MsMs31752Specdb::MsMs31753Specdb::MsMs1471327Specdb::MsMs1471329Specdb::MsMs1471920Specdb::MsMs1471921Specdb::MsMs1471922Specdb::MsMs1471923Specdb::MsMs1471924Specdb::MsMs1471925Specdb::MsMs1471926Specdb::MsMs1471927Specdb::MsMs1471928Specdb::MsMs1471929Specdb::MsMs1471930Specdb::MsMs1471931Specdb::MsMs1471932Specdb::MsMs1471933Specdb::MsMs1471934Specdb::MsMs1471935Specdb::MsMs1471936102679848C0537828013FRUCTOSE-16-DIPHOSPHATEFBPKeseler, 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-D114.22080510Bennett, 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 5:593-599.19561621Buchholz, A., Takors, R., Wandrey, C. (2001). "Quantification of intracellular metabolites in Escherichia coli K12 using liquid chromatographic-electrospray ionization tandem mass spectrometric techniques." Anal Biochem 295:129-137.11488613Peng, L., Arauzo-Bravo, M. J., Shimizu, K. (2004). "Metabolic flux analysis for a ppc mutant Escherichia coli based on 13C-labelling experiments together with enzyme activity assays and intracellular metabolite measurements." FEMS Microbiol Lett 235:17-23.15158257Park, 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.Kornberg, H., Lourenco, C. (2006). "A route for fructose utilization by Escherichia coli involving the fucose regulon." Proc Natl Acad Sci U S A 103:19496-19499.17159144Daldal, F., Fraenkel, D. G. (1983). "Assessment of a futile cycle involving reconversion of fructose 6-phosphate to fructose 1,6-bisphosphate during gluconeogenic growth of Escherichia coli." J Bacteriol 153:390-394.6217196Izard, T., Sygusch, J. (2004). "Induced fit movements and metal cofactor selectivity of class II aldolases: structure of Thermus aquaticus fructose-1,6-bisphosphate aldolase." J Biol Chem 279:11825-11833.14699122Nghiem, N. P., Cofer, T. M. (2007). "Effect of a nonmetabolizable analog of fructose-1,6-bisphosphate on glycolysis and ethanol production in strains of Saccharomyces cerevisiae and Escherichia coli." Appl Biochem Biotechnol 141:335-347.18025560Veiga-da-Cunha, M., Hoyoux, A., Van Schaftingen, E. (2000). "Overexpression and purification of fructose-1-phosphate kinase from Escherichia coli: application to the assay of fructose 1-phosphate." Protein Expr Purif 19:48-52.108333896-phosphofructokinase isozyme 2P06999K6PF2_ECOLIpfkBhttp://ecmdb.ca/proteins/P06999.xml6-phosphofructokinase isozyme 1P0A796K6PF1_ECOLIpfkAhttp://ecmdb.ca/proteins/P0A796.xmlFructose-bisphosphate aldolase class 1P0A991ALF1_ECOLIfbaBhttp://ecmdb.ca/proteins/P0A991.xmlFructose-1,6-bisphosphatase class 1P0A993F16PA_ECOLIfbphttp://ecmdb.ca/proteins/P0A993.xmlFructose-1,6-bisphosphatase class 2P0A9C9GLPX_ECOLIglpXhttp://ecmdb.ca/proteins/P0A9C9.xmlFructose-bisphosphate aldolase class 2P0AB71ALF_ECOLIfbaAhttp://ecmdb.ca/proteins/P0AB71.xml1-phosphofructokinaseP0AEW9K1PF_ECOLIfruKhttp://ecmdb.ca/proteins/P0AEW9.xmlbeta-D-Fructose 1,6-bisphosphate <> Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphateR01070Adenosine triphosphate + Fructose 1-phosphate <> ADP + beta-D-Fructose 1,6-bisphosphateR02071Adenosine triphosphate + beta-D-Fructose 6-phosphate <> ADP + beta-D-Fructose 1,6-bisphosphateR04779beta-D-Fructose 1,6-bisphosphate + Water <> beta-D-Fructose 6-phosphate + PhosphateR04780Adenosine triphosphate + Fructose 1-phosphate <> ADP + beta-D-Fructose 1,6-bisphosphate4.0 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 glucoseBioreactor, pH controlled, aerated, dilution rate=0.125 L/h85.2uM0.037 oCW3110Mid Log Phase3408000Park, 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 glucoseBioreactor, pH controlled, aerated4.7uM0.037 oCW3110Stationary Phase188000Park, 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: 524-530.0.2 g/L NH4Cl, 2.0 g/L (NH4)2SO4, 3.25 g/L KH2PO4, 2.5 g/L K2HPO4, 1.5 g/L NaH2PO4, 0.5 g/L MgSO4; trace substances: 10 mg/L CaCl2, 0.5 mg/L ZnSO4, 0.25 mg/L CuCl2, 0.25 mg/L MnSO4, 0.175 mg/L CoCl2, 0.125 mg/L H3BO3, 2.5 mg/L AlCl3, 0.5 mg/L Na2MoO4, 10Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h3290.0uM179.037 oCK12Stationary Phase, glucose limited13160000716000Buchholz, A., Takors, R., Wandrey, C. (2001). "Quantification of intracellular metabolites in Escherichia coli K12 using liquid chromatographic-electrospray ionization tandem mass spectrometric techniques." Anal Biochem 295:129-137.11488613M9 Minimal Media, 4 g/L GlucoseBioreactor, pH controlled, O2 controlled, dilution rate: 0.2/h1010.0uM100.037 oCBW25113Mid-Log Phase4040000400000Peng, L., Arauzo-Bravo, M. J., Shimizu, K. (2004). "Metabolic flux analysis for a ppc mutant Escherichia coli based on 13C-labelling experiments together with enzyme activity assays and intracellular metabolite measurements." FEMS Microbiol Lett 235:17-23.15158257Gutnick 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 glucoseShake flask and filter culture15200.0uM0.037 oCK12 NCM3722Mid-Log Phase608000000Bennett, 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 5:593-599.19561621Gutnick 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 glycerolShake flask and filter culture5850.0uM0.037 oCK12 NCM3722Mid-Log Phase234000000Bennett, 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 5:593-599.19561621Gutnick 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 acetateShake flask and filter culture152.0uM0.037 oCK12 NCM3722Mid-Log Phase6080000Bennett, 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