2.0 2012-05-31 14:28:42 -0600 2015-06-03 17:19:21 -0600 ECMDB20123 M2MDB000971 beta-D-Fructose 1,6-bisphosphate Beta-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) &beta;-D-fructose-1,6-diphosphate &beta;-D-fructose-1,6-diphosphoric acid 1,6-Di-O-phosphono-b-D-fructofuranose 1,6-Di-O-phosphono-beta-D-fructofuranose 1,6-Di-O-phosphono-β-D-fructofuranose 6055-82-9 (Calcium[1:2] salt) b Fructose 1,6-diphosphate b Fructose 1,6-diphosphoric acid b-D-Fructofuranose 1,6-bis(dihydrogen phosphate) b-D-Fructofuranose 1,6-bis(dihydrogen phosphoric acid) b-D-Fructofuranose 1,6-bisphosphate b-D-Fructofuranose 1,6-bisphosphoric acid b-D-Fructofuranose, 1,6-bis(dihydrogen phosphate) b-D-Fructofuranose, 1,6-bis(dihydrogen phosphoric acid) b-D-Fructose 1,6-bisphosphate b-D-Fructose 1,6-bisphosphoric acid b-D-Fructose-1,6-diphosphate b-D-Fructose-1,6-diphosphoric acid Beta Fructose 1,6-diphosphate beta Fructose 1,6-diphosphoric acid Beta-D-Fructofuranose 1,6-bis(dihydrogen phosphate) beta-D-Fructofuranose 1,6-bis(dihydrogen phosphoric acid) Beta-D-Fructofuranose 1,6-bisphosphate beta-D-Fructofuranose 1,6-bisphosphoric acid Beta-D-Fructofuranose, 1,6-bis(dihydrogen phosphate) beta-D-Fructofuranose, 1,6-bis(dihydrogen phosphoric acid) beta-D-Fructose 1,6-bisphosphoric acid Beta-D-Fructose-1,6-diphosphate beta-D-Fructose-1,6-diphosphoric acid BFP D-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-bisphosphate D-Fructose-1,6-bisphosphoric acid D-Fructose-1,6-diphosphate D-Fructose-1,6-diphosphoric acid FBP Fructose 1,6-bisphosphate Fructose 1,6-bisphosphoric acid Fructose 1,6-diphosphate Fructose 1,6-diphosphoric acid Fructose-1,6-biphosphate Fructose-1,6-biphosphoric acid Fructose-1,6-bisphosphate Fructose-1,6-bisphosphoric acid Fructose-1,6-diphosphate Fructose-1,6-diphosphoric acid Harden-young-ester β Fructose 1,6-diphosphate β Fructose 1,6-diphosphoric acid β-D-Fructofuranose 1,6-bis(dihydrogen phosphate) β-D-Fructofuranose 1,6-bis(dihydrogen phosphoric acid) β-D-Fructofuranose 1,6-bisphosphate β-D-Fructofuranose 1,6-bisphosphoric acid β-D-Fructofuranose, 1,6-bis(dihydrogen phosphate) β-D-Fructofuranose, 1,6-bis(dihydrogen phosphoric acid) β-D-Fructose 1,6-bisphosphate β-D-Fructose 1,6-bisphosphoric acid β-D-Fructose-1,6-diphosphate β-D-Fructose-1,6-diphosphoric acid C6H14O12P2 340.1157 339.996048936 {[(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 acid 125740-83-2 O[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O InChI=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/s1 RNBGYGVWRKECFJ-ARQDHWQXSA-N Cytoplasm Periplasm logp -1.51 ALOGPS logs -1.33 ALOGPS solubility 1.61e+01 g/l ALOGPS logp -3 ChemAxon pka_strongest_acidic 0.89 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac {[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 340.1157 ChemAxon mono_mass 339.996048936 ChemAxon smiles O[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O ChemAxon formula C6H14O12P2 ChemAxon inchi InChI=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/s1 ChemAxon inchikey RNBGYGVWRKECFJ-ARQDHWQXSA-N ChemAxon polar_surface_area 203.44 ChemAxon refractivity 58.11 ChemAxon polarizability 25.7 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Glycolysis / Gluconeogenesis ec00010 Fructose and mannose metabolism ec00051 Microbial metabolism in diverse environments ec01120 gluconeogenesis I GLUCONEO-PWY glycolysis I GLYCOLYSIS fructose degradation PWY0-1314 Specdb::CMs 2061 Specdb::CMs 2080 Specdb::CMs 2081 Specdb::CMs 36588 Specdb::CMs 48214 Specdb::CMs 174473 Specdb::NmrOneD 8462 Specdb::NmrOneD 8463 Specdb::NmrOneD 8464 Specdb::NmrOneD 8465 Specdb::NmrOneD 8466 Specdb::NmrOneD 8467 Specdb::NmrOneD 8468 Specdb::NmrOneD 8469 Specdb::NmrOneD 8470 Specdb::NmrOneD 8471 Specdb::NmrOneD 8472 Specdb::NmrOneD 8473 Specdb::NmrOneD 8474 Specdb::NmrOneD 8475 Specdb::NmrOneD 8476 Specdb::NmrOneD 8477 Specdb::NmrOneD 8478 Specdb::NmrOneD 8479 Specdb::NmrOneD 8480 Specdb::NmrOneD 8481 Specdb::MsMs 25193 Specdb::MsMs 25194 Specdb::MsMs 25195 Specdb::MsMs 31751 Specdb::MsMs 31752 Specdb::MsMs 31753 Specdb::MsMs 1471327 Specdb::MsMs 1471329 Specdb::MsMs 1471920 Specdb::MsMs 1471921 Specdb::MsMs 1471922 Specdb::MsMs 1471923 Specdb::MsMs 1471924 Specdb::MsMs 1471925 Specdb::MsMs 1471926 Specdb::MsMs 1471927 Specdb::MsMs 1471928 Specdb::MsMs 1471929 Specdb::MsMs 1471930 Specdb::MsMs 1471931 Specdb::MsMs 1471932 Specdb::MsMs 1471933 Specdb::MsMs 1471934 Specdb::MsMs 1471935 Specdb::MsMs 1471936 10267 9848 C05378 28013 FRUCTOSE-16-DIPHOSPHATE FBP 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 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 Buchholz, 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. 11488613 Peng, 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. 15158257 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. 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. 17159144 Daldal, 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. 6217196 Izard, 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. 14699122 Nghiem, 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. 18025560 Veiga-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. 10833389 6-phosphofructokinase isozyme 2 P06999 K6PF2_ECOLI pfkB http://ecmdb.ca/proteins/P06999.xml 6-phosphofructokinase isozyme 1 P0A796 K6PF1_ECOLI pfkA http://ecmdb.ca/proteins/P0A796.xml Fructose-bisphosphate aldolase class 1 P0A991 ALF1_ECOLI fbaB http://ecmdb.ca/proteins/P0A991.xml Fructose-1,6-bisphosphatase class 1 P0A993 F16PA_ECOLI fbp http://ecmdb.ca/proteins/P0A993.xml Fructose-1,6-bisphosphatase class 2 P0A9C9 GLPX_ECOLI glpX http://ecmdb.ca/proteins/P0A9C9.xml Fructose-bisphosphate aldolase class 2 P0AB71 ALF_ECOLI fbaA http://ecmdb.ca/proteins/P0AB71.xml 1-phosphofructokinase P0AEW9 K1PF_ECOLI fruK http://ecmdb.ca/proteins/P0AEW9.xml beta-D-Fructose 1,6-bisphosphate <> Dihydroxyacetone phosphate + D-Glyceraldehyde 3-phosphate R01070 Adenosine triphosphate + Fructose 1-phosphate <> ADP + beta-D-Fructose 1,6-bisphosphate R02071 Adenosine triphosphate + beta-D-Fructose 6-phosphate <> ADP + beta-D-Fructose 1,6-bisphosphate R04779 beta-D-Fructose 1,6-bisphosphate + Water <> beta-D-Fructose 6-phosphate + Phosphate R04780 Adenosine triphosphate + Fructose 1-phosphate <> ADP + beta-D-Fructose 1,6-bisphosphate 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 85.2 uM 0.0 37 oC W3110 Mid Log Phase 340800 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 4.7 uM 0.0 37 oC W3110 Stationary Phase 18800 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. 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, 10 Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h 3290.0 uM 179.0 37 oC K12 Stationary Phase, glucose limited 13160000 716000 Buchholz, 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. 11488613 M9 Minimal Media, 4 g/L Glucose Bioreactor, pH controlled, O2 controlled, dilution rate: 0.2/h 1010.0 uM 100.0 37 oC BW25113 Mid-Log Phase 4040000 400000 Peng, 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. 15158257 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 15200.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 60800000 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 glycerol Shake flask and filter culture 5850.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 23400000 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 152.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 608000 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