2.0 2012-05-31 13:56:48 -0600 2015-06-03 15:54:17 -0600 ECMDB02649 M2MDB000460 D-Erythrose 4-phosphate D-Erythrose 4-phosphate is a phosphorylated derivative of erythrose that serves as an important intermediate in the pentose phosphate pathway. It is also used in phenylalanine, tyrosine and tryptophan biosynthesis, and it plays a role in vitamin B6 metabolism (KEGG) D-Erythrose 4-phosphate D-Erythrose 4-phosphoric acid D-Erythrose 4-PO4 D-Erythrose-4-P D-Erythrose-4-phosphate D-Erythrose-4-phosphoric acid E4P Erythrose 4-phosphate Erythrose 4-phosphoric acid Erythrose 4-PO4 Erythrose-4-P Erythrose-4-phosphate Erythrose-4-phosphoric acid Erythrose-4P Threose 4-phosphate Threose 4-phosphoric acid C4H9O7P 200.0838 200.008589154 [(2R,3R)-2,3-dihydroxy-4-oxobutoxy]phosphonic acid 4-O-phosphono-D-erythrose 585-18-2 O[C@H](COP(O)(O)=O)[C@@H](O)C=O InChI=1S/C4H9O7P/c5-1-3(6)4(7)2-11-12(8,9)10/h1,3-4,6-7H,2H2,(H2,8,9,10)/t3-,4+/m0/s1 NGHMDNPXVRFFGS-IUYQGCFVSA-N Solid Cytosol logp -1.89 ALOGPS logs -0.93 ALOGPS solubility 2.37e+01 g/l ALOGPS logp -2.4 ChemAxon pka_strongest_acidic 1.48 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac [(2R,3R)-2,3-dihydroxy-4-oxobutoxy]phosphonic acid ChemAxon average_mass 200.0838 ChemAxon mono_mass 200.008589154 ChemAxon smiles O[C@H](COP(O)(O)=O)[C@@H](O)C=O ChemAxon formula C4H9O7P ChemAxon inchi InChI=1S/C4H9O7P/c5-1-3(6)4(7)2-11-12(8,9)10/h1,3-4,6-7H,2H2,(H2,8,9,10)/t3-,4+/m0/s1 ChemAxon inchikey NGHMDNPXVRFFGS-IUYQGCFVSA-N ChemAxon polar_surface_area 124.29 ChemAxon refractivity 36.29 ChemAxon polarizability 15.41 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Vitamin B6 metabolism ec00750 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Chorismate biosynthesis Chorismate is an intermediate in the synthesis of three amino acids: tyrosine, phenylalanine and tryptophan. In addition it is a precursor of folic acid, ubiquinone, menaquinone, and enterochelin. The first reaction in the chorismate pathway is catalyzed by three separate enzymes, all involved in the biosynthesis of Shikimic acid, each of which is subject to feedback inhibition by one of the three amino acids. However, even in the presence of all three amino acids, sufficient enzymatic activity is present to permit synthesis of the other four metabolites synthesized from chorismate because the enzyme subject to regulation by tryptophan cannot be inhibited more than 60 percent. The biosynthesis of chorismate starts with D-Erythrose-4-phosphate getting transformed into 3-deoxy-D-arabino-heptulosonate-7-phosphate through a phospho-2-dehydro-3-deoxyheptonate aldolase. This is followed by a 3-dehydroquinate synthase converting the 3-deoxy-D-arabino-heptulosonate-7-phosphate into a 3-dehydroquinate which in turn is conveted to 3-dehydroshikimate through a 3-dehydroquinate dehydratase. A this point 3-dehydroshikimate can be turned into Shikimic acid through 2 different reactions involving Quinate/shikimate dehydrogenase and shikimate dehydrogenase 2. Shikimic acid is phosphorylated by Shikimate kinase 2 into shikimate 3-phosphate. Shikimate 3- phophate and a phosphoenolpyruvic acid are then joined through a 3-phosphoshikimate 1-carboxyvinyltransferase to produce a 5-enoylpyruvyl-shikimate 3-phosphate while releasing a phosphate. This in turns produces our final product Chorismate through a chorismate synthase. PW000816 Metabolic Pentose Phosphate PW000893 Metabolic Secondary Metabolites: Shikimate Pathway The biosynthesis of shikimate starts with D-Erythrose-4-phosphate getting transformed into 3-deoxy-D-arabino-heptulosonate-7-phosphate through a phospho-2-dehydro-3-deoxyheptonate aldolase. This is followed by a 3-dehydroquinate synthase converting the 3-deoxy-D-arabino-heptulosonate-7-phosphate into a 3-dehydroquinate which in turn is conveted to 3-dehydroshikimate through a 3-dehydroquinate dehydratase. A this point 3-dehydroshikimate can be turned into Shikimic acid through 2 different reactions involving an NADPH driven Quinate/shikimate dehydrogenase or a NADPH driven shikimate dehydrogenase 2. Shikimate can also be transported through a shikimate:H+ symporter. PW000985 Metabolic Vitamin B6 1430936196 PW000891 Metabolic Sedoheptulose Bisphosphate Bypass Accumulation of D-sedoheptulose 7-phosphate, an intermediate of the pentose phosphate pathway (non-oxidative branch), leads to its utilization via the sedoheptulose bisphospate bypass pathway, described here. The pathway was discovered due to the unexpected near-wild type growth of a talA talB double null mutant on xylose. 6-Phosphofructokinase I is able to phosphorylate D-sedoheptulose 7-phosphate, producing D-sedoheptulose-1,7-bisphosphate, which is in turn split into glycerone phosphate and D-erythrose 4-phosphate by fructose bisphosphate aldolase. PW002098 Metabolic pentose phosphate pathway (non-oxidative branch) NONOXIPENT-PWY pyridoxal 5'-phosphate biosynthesis I PYRIDOXSYN-PWY 3-dehydroquinate biosynthesis I PWY-6164 sedoheptulose bisphosphate bypass PWY0-1517 Specdb::CMs 1625 Specdb::CMs 1638 Specdb::CMs 3160 Specdb::CMs 31311 Specdb::CMs 31312 Specdb::CMs 32343 Specdb::CMs 32344 Specdb::CMs 38023 Specdb::CMs 160944 Specdb::NmrOneD 9182 Specdb::NmrOneD 9183 Specdb::NmrOneD 9184 Specdb::NmrOneD 9185 Specdb::NmrOneD 9186 Specdb::NmrOneD 9187 Specdb::NmrOneD 9188 Specdb::NmrOneD 9189 Specdb::NmrOneD 9190 Specdb::NmrOneD 9191 Specdb::NmrOneD 9192 Specdb::NmrOneD 9193 Specdb::NmrOneD 9194 Specdb::NmrOneD 9195 Specdb::NmrOneD 9196 Specdb::NmrOneD 9197 Specdb::NmrOneD 9198 Specdb::NmrOneD 9199 Specdb::NmrOneD 9200 Specdb::NmrOneD 9201 Specdb::MsMs 27413 Specdb::MsMs 27414 Specdb::MsMs 27415 Specdb::MsMs 33971 Specdb::MsMs 33972 Specdb::MsMs 33973 Specdb::MsMs 439060 Specdb::MsMs 1473421 Specdb::MsMs 1473422 Specdb::MsMs 3052106 Specdb::MsMs 3052107 Specdb::MsMs 3052108 Specdb::MsMs 3114833 Specdb::MsMs 3114834 Specdb::MsMs 3114835 HMDB01321 697 109096 C00279 16897 ERYTHROSE-4P E4P erythrose-4-phosphate Keseler, I. 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"Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 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. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. 15882454 Tanaka N, Haga A, Uemura H, Akiyama H, Funasaka T, Nagase H, Raz A, Nakamura KT: Inhibition mechanism of cytokine activity of human autocrine motility factor examined by crystal structure analyses and site-directed mutagenesis studies. J Mol Biol. 2002 May 10;318(4):985-97. 12054796 Huck JH, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS: Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: application to transaldolase deficiency. Clin Chem. 2003 Aug;49(8):1375-80. 12881455 Takeuchi T, Nishino K, Itokawa Y: Improved determination of transketolase activity in erythrocytes. Clin Chem. 1984 May;30(5):658-61. 6713626 Talukder AH, Bagheri-Yarmand R, Williams RR, Ragoussis J, Kumar R, Raz A: Antihuman epidermal growth factor receptor 2 antibody herceptin inhibits autocrine motility factor (AMF) expression and potentiates antitumor effects of AMF inhibitors. Clin Cancer Res. 2002 Oct;8(10):3285-9. 12374700 Stepanova NG: [Determination of aldolase A activity in the serum of patients with myocardial infarction] Vopr Med Khim. 1986 Sep-Oct;32(5):89-93. 3776121 Mikami M, Sadahira Y, Haga A, Otsuki T, Wada H, Sugihara T: Hypoxia-inducible factor-1 drives the motility of the erythroid progenitor cell line, UT-7/Epo, via autocrine motility factor. Exp Hematol. 2005 May;33(5):531-41. 15850830 Zanella A, Izzo C, Rebulla P, Perroni L, Mariani M, Canestri G, Sansone G, Sirchia G: The first stable variant of erythrocyte glucose-phosphate isomerase associated with severe hemolytic anemia. Am J Hematol. 1980;9(1):1-11. 7435496 Williams JF, Blackmore PF, Duke CC, MacLeod JK: Fact, uncertainty and speculation concerning the biochemistry of D-erythrose-4-phosphate and its metabolic roles. Int J Biochem. 1980;12(3):339-44. 6998788 Phospho-2-dehydro-3-deoxyheptonate aldolase, Trp-sensitive P00887 AROH_ECOLI aroH http://ecmdb.ca/proteins/P00887.xml Phospho-2-dehydro-3-deoxyheptonate aldolase, Tyr-sensitive P00888 AROF_ECOLI aroF http://ecmdb.ca/proteins/P00888.xml Transaldolase A P0A867 TALA_ECOLI talA http://ecmdb.ca/proteins/P0A867.xml Transaldolase B P0A870 TALB_ECOLI talB http://ecmdb.ca/proteins/P0A870.xml Fructose-bisphosphate aldolase class 1 P0A991 ALF1_ECOLI fbaB http://ecmdb.ca/proteins/P0A991.xml Glyceraldehyde-3-phosphate dehydrogenase A P0A9B2 G3P1_ECOLI gapA http://ecmdb.ca/proteins/P0A9B2.xml D-erythrose-4-phosphate dehydrogenase P0A9B6 E4PD_ECOLI epd http://ecmdb.ca/proteins/P0A9B6.xml Fructose-bisphosphate aldolase class 2 P0AB71 ALF_ECOLI fbaA http://ecmdb.ca/proteins/P0AB71.xml Phospho-2-dehydro-3-deoxyheptonate aldolase, Phe-sensitive P0AB91 AROG_ECOLI aroG http://ecmdb.ca/proteins/P0AB91.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 Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml PTS system N-acetylmuramic acid-specific EIIBC component P77272 PTYBC_ECOLI murP http://ecmdb.ca/proteins/P77272.xml PTS system N-acetylmuramic acid-specific EIIBC component P77272 PTYBC_ECOLI murP http://ecmdb.ca/proteins/P77272.xml D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate <> D-Erythrose 4-phosphate + Fructose 6-phosphate TRANSALDOL-RXN D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <> 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate R01826 DAHPSYN-RXN D-Erythrose 4-phosphate + Water + NAD <> 4-Phospho-D-erythronate +2 Hydrogen ion + NADH R01825 ERYTH4PDEHYDROG-RXN D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate R01067 2TRANSKETO-RXN Sedoheptulose 1,7-bisphosphate <> Dihydroxyacetone phosphate + D-Erythrose 4-phosphate R01829 SEDOBISALDOL-RXN Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate R01067 D-Erythrose 4-phosphate + NAD + Water <> 4-Phospho-D-erythronate + NADH + Hydrogen ion R01825 Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + beta-D-Fructose 6-phosphate R01827 beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + Xylulose 5-phosphate R01830 D-Erythrose 4-phosphate + Water + NAD > 4-Phospho-D-erythronate + NADH + Hydrogen ion ERYTH4PDEHYDROG-RXN Dihydroxyacetone phosphate + D-Erythrose 4-phosphate < Sedoheptulose 1,7-bisphosphate SEDOBISALDOL-RXN Phosphoenolpyruvic acid + D-Erythrose 4-phosphate + Water > 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Inorganic phosphate D-Erythrose 4-phosphate + NAD + Water > 4-Phospho-D-erythronate + NADH Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate > D-Erythrose 4-phosphate + Fructose 6-phosphate D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> beta-D-Fructose 6-phosphate + D-Erythrose 4-phosphate PW_R003347 D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid > Phosphate + 3-deoxy-D-arabino-heptulosonate-7-phosphate PW_R002910 Erythrose + Erythrose > D-Erythrose 4-phosphate + CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/19:0cycv8c) + CL(17:0cycw7c/16:0/17:0cycw7c/16:1(9Z)) PW_RCT000130 D-Erythrose 4-phosphate + NAD + Water > 4-Phospho-D-erythronate + NADH +2 Hydrogen ion PW_R006051 Sedoheptulose 1,7-bisphosphate > D-Erythrose 4-phosphate + Glycerone phosphate PW_R006121 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-Erythrose 4-phosphate + Water + NAD <>4 4-Phospho-D-erythronate +2 Hydrogen ion + NADH D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <>2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + beta-D-Fructose 6-phosphate D-Erythrose 4-phosphate + Xylulose 5-phosphate <> Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <>2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + beta-D-Fructose 6-phosphate D-Erythrose 4-phosphate + Water + NAD <>4 4-Phospho-D-erythronate +2 Hydrogen ion + NADH 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 1.3 uM 0.0 37 oC W3110 Mid Log Phase 5200 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 2.8 uM 0.0 37 oC W3110 Stationary Phase 11200 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.