Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 14:28:42 -0600 |
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Update Date | 2015-06-03 17:19:21 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | beta-D-Fructose 1,6-bisphosphate |
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Description | 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) |
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Structure | |
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Synonyms: | - β-D-fructose-1,6-diphosphate
- β-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
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Chemical Formula: | C6H14O12P2 |
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Weight: | Average: 340.1157 Monoisotopic: 339.996048936 |
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InChI Key: | RNBGYGVWRKECFJ-ARQDHWQXSA-N |
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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 |
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CAS number: | 125740-83-2 |
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IUPAC Name: | {[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid |
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Traditional IUPAC Name: | [(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid |
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SMILES: | O[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Hexose phosphates |
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Alternative Parents | |
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Substituents | - Hexose phosphate
- Pentose phosphate
- Pentose-5-phosphate
- C-glycosyl compound
- Glycosyl compound
- Monosaccharide phosphate
- Pentose monosaccharide
- Monoalkyl phosphate
- Organic phosphoric acid derivative
- Alkyl phosphate
- Phosphoric acid ester
- Tetrahydrofuran
- 1,2-diol
- Hemiacetal
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Not Available |
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Charge: | -4 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | - Fructose and mannose metabolism ec00051
- Glycolysis / Gluconeogenesis ec00010
- Microbial metabolism in diverse environments ec01120
- Pentose phosphate pathway ec00030
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EcoCyc Pathways: | |
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Concentrations |
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| Concentration | Strain | Media | Growth Status | Growth System | Temperature | Details |
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85± 0 uM | W3110 | 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 | Mid Log Phase | Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h | 37 oC | 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. | 5± 0 uM | W3110 | 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 | Stationary Phase | Bioreactor, pH controlled, aerated | 37 oC | 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. | 3290± 179 uM | K12 | 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 | Stationary Phase, glucose limited | Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h | 37 oC | PMID: 11488613 | 1010± 100 uM | BW25113 | M9 Minimal Media, 4 g/L Glucose | Mid-Log Phase | Bioreactor, pH controlled, O2 controlled, dilution rate: 0.2/h | 37 oC | PMID: 15158257 | 15200± 0 uM | K12 NCM3722 | 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 | Mid-Log Phase | Shake flask and filter culture | 37 oC | PMID: 19561621 | 5850± 0 uM | K12 NCM3722 | 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 | Mid-Log Phase | Shake flask and filter culture | 37 oC | PMID: 19561621 | 152± 0 uM | K12 NCM3722 | 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 | Mid-Log Phase | Shake flask and filter culture | 37 oC | PMID: 19561621 |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (7 TMS) | splash10-014i-0497100000-d0c0dfadfe65ee3cc4e5 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 7 TMS) | splash10-014r-1779100000-ba60994aacef73cf8691 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 7 TMS) | splash10-014r-0779100000-b52ccd042ce4169961ed | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-01xt-9532000000-c3c4929a4987e34c0dc0 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-03fs-9412510000-0a0a9e96cc6bea61e3c7 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 23V, negative | splash10-0006-0190000000-95a4b5217606c0b9d1fb | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 23V, negative | splash10-0002-0900000000-74a1700e0fae0f6aa64e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, negative | splash10-000i-0009000000-631b4fa683b46f4c89cb | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 8V, negative | splash10-000i-1009000000-9df66c58adba653741e0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 10V, negative | splash10-000j-7129000000-f1414a0a896a7c132d2d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 14V, negative | splash10-0002-9111000000-0fc51e8f6b123f0a5982 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 18V, negative | splash10-0002-9100000000-762070874ad885772dc4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 21V, negative | splash10-0002-9100000000-d705002b3a24c5b5ac0f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 25V, negative | splash10-002b-9000000000-caf9814ab914b2093561 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 29V, negative | splash10-004j-9000000000-3b04f1a6a67ed239b001 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 33V, negative | splash10-004i-9000000000-388ef99a8af7f88e6447 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 41V, negative | splash10-004i-9000000000-bc85bd9d38f2c4bf3c58 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 23V, negative | splash10-0006-0190000000-ba22a78fbbfc1a90ace3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 23V, negative | splash10-0a4i-0900000000-b559d4679fc0eaa79be7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 23V, negative | splash10-004i-9000000000-5ef060d5ec4b80c35c1a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 23V, negative | splash10-0002-9530000000-8e5076b641ebc42fb2ef | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 23V, negative | splash10-004i-9000000000-5ef060d5ec4b80c35c1a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 23V, negative | splash10-0fdk-9870000000-6332e12e884d56a6c22b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - n/a 23V, negative | splash10-004i-9000000000-5ef060d5ec4b80c35c1a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0007-6469000000-934f8ed1edcbd28bc667 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-006y-7295000000-a5ca0806e65ba8c99e88 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0005-9700000000-02fcc2f4b95b801c5949 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-002r-8509000000-2992f67772e061c3ffe5 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-9ac5383c77bff5f6cb96 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-9d902dae0eabfe2165da | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - 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. Pubmed: 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. Pubmed: 11488613
- 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. Pubmed: 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. Pubmed: 14699122
- 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. Pubmed: 22080510
- 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. Pubmed: 21097882
- 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. Pubmed: 17159144
- 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. Pubmed: 18025560
- 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.
- 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. Pubmed: 15158257
- 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. Pubmed: 10833389
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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