2.0 2012-05-31 14:01:34 -0600 2015-06-03 15:54:35 -0600 ECMDB03971 M2MDB000547 beta-D-Fructose 6-phosphate Beta-D-Fructose 6 phosphate (b-F6P) is the beta-anomer of fructose-6-phosphate. There are two anomers of fructose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-fructose 6-phosphate is fructose sugar phosphorylated on carbon 6. Beta-D-Fructose 6-phosphate is a substrate for Fructose-1,6-bisphosphatase, Pyruvate kinase (isozymes R/L), Hexokinase (type I), Fructose-bisphosphate aldolase A, L-lactate dehydrogenase B chain, Glyceraldehyde-3-phosphate dehydrogenase and Transaldolase. &beta;-D-fructofuranose 6-phosphate &beta;-D-fructofuranose 6-phosphoric acid A-D-Fructose-6-P b-D-Fructofuranose 6-phosphate b-D-Fructofuranose 6-phosphoric acid b-D-Fructose 6-phosphate b-D-Fructose 6-phosphoric acid Beta-D-Fructofuranose 6-phosphate beta-D-Fructofuranose 6-phosphoric acid Beta-D-Fructose 6-phosphate beta-D-Fructose 6-phosphoric acid D-Fructofuranose 6-phosphate D-Fructofuranose 6-phosphoric acid D-Fructose-6-P D-Fructose-6-phosphate D-Fructose-6-phosphoric acid F6P Fru-6-P Fruc6p Fructose-6-P Fructose-6-phosphate Fructose-6-phosphoric acid Fructose-6P β-D-Fructofuranose 6-phosphate β-D-Fructofuranose 6-phosphoric acid β-D-Fructose 6-phosphate β-D-Fructose 6-phosphoric acid C6H13O9P 260.1358 260.029718526 {[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid β-D-fructofuranose 6-phosphate OC[C@@]1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O InChI=1S/C6H13O9P/c7-2-6(10)5(9)4(8)3(15-6)1-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1 BGWGXPAPYGQALX-ARQDHWQXSA-N Solid Cytoplasm Periplasm logp -2.11 ALOGPS logs -0.89 ALOGPS solubility 3.34e+01 g/l ALOGPS logp -2.9 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac {[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 260.1358 ChemAxon mono_mass 260.029718526 ChemAxon smiles OC[C@@]1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O ChemAxon formula C6H13O9P ChemAxon inchi InChI=1S/C6H13O9P/c7-2-6(10)5(9)4(8)3(15-6)1-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1 ChemAxon inchikey BGWGXPAPYGQALX-ARQDHWQXSA-N ChemAxon polar_surface_area 156.91 ChemAxon refractivity 47.23 ChemAxon polarizability 20.92 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Starch and sucrose metabolism The metabolism of starch and sucrose begins with D-fructose interacting with a D-glucose in a reversible reaction through a maltodextrin glucosidase resulting in a water molecule and a sucrose. D-fructose is phosphorylated through an ATP driven fructokinase resulting in the release of an ADP, a hydrogen ion and a Beta-D-fructofuranose 6-phosphate. This compound can also be introduced into the cytoplasm through either a mannose PTS permease or a hexose-6-phosphate:phosphate antiporter. The Beta-D-fructofuranose 6-phosphate is isomerized through a phosphoglucose isomerase resulting in a Beta-D-glucose 6-phosphate. This compound can also be incorporated by glucose PTS permease or a hexose-6-phosphate:phosphate antiporter. The beta-D-glucose 6 phosphate can also be produced by a D-glucose being phosphorylated by an ATP-driven glucokinase resulting in a ADP, a hydrogen ion and a Beta-D-glucose 6 phosphate. The beta-D-glucose can produce alpha-D-glucose-1-phosphate by two methods: 1.-Beta-D-glucose is isomerized into an alpha-D-Glucose 6-phosphate and then interacts in a reversible reaction through a phosphoglucomutase-1 resulting in a alpha-D-glucose-1-phosphate. 2.-Beta-D-glucose interacts with a putative beta-phosphoglucomutase resulting in a Beta-D-glucose 1-phosphate. Beta-D-glucose 1-phosphate can be incorporated into the cytoplasm through a glucose PTS permease. This compound is then isomerized into a Alpha-D-glucose-1-phosphate The beta-D-glucose can cycle back into a D-fructose by first interacting with D-fructose in a reversible reaction through a Polypeptide: predicted glucosyltransferase resulting in the release of a phosphate and a sucrose. The sucrose then interacts in a reversible reaction with a water molecule through a maltodextrin glucosidase resulting in a D-glucose and a D-fructose. Alpha-D-glucose-1-phosphate can produce glycogen in by two different sets of reactions: 1.-Alpha-D-glucose-1-phosphate interacts with a hydrogen ion and an ATP through a glucose-1-phosphate adenylyltransferase resulting in a pyrophosphate and an ADP-glucose. The ADP-glucose then interacts with an amylose through a glycogen synthase resulting in the release of an ADP and an Amylose. The amylose then interacts with 1,4-α-glucan branching enzyme resulting in glycogen 2.- Alpha-D-glucose-1-phosphate interacts with amylose through a maltodextrin phosphorylase resulting in a phosphate and a glycogen. Alpha-D-glucose-1-phosphate can also interacts with UDP-galactose through a galactose-1-phosphate uridylyltransferase resulting in a galactose 1-phosphate and a Uridine diphosphate glucose. The UDP-glucose then interacts with an alpha-D-glucose 6-phosphate through a trehalose-6-phosphate synthase resulting in a uridine 5'-diphosphate, a hydrogen ion and a Trehalose 6- phosphate. The latter compound can also be incorporated into the cytoplasm through a trehalose PTS permease. Trehalose interacts with a water molecule through a trehalose-6-phosphate phosphatase resulting in the release of a phosphate and an alpha,alpha-trehalose.The alpha,alpha-trehalose can also be obtained from glycogen being metabolized through a glycogen debranching enzyme resulting in a the alpha, alpha-trehalose. This compound ca then be hydrated through a cytoplasmic trehalase resulting in the release of an alpha-D-glucose and a beta-d-glucose. Glycogen is then metabolized by reacting with a phosphate through a glycogen phosphorylase resulting in a alpha-D-glucose-1-phosphate and a dextrin. The dextrin is then hydrated through a glycogen phosphorylase-limit dextrin α-1,6-glucohydrolase resulting in the release of a debranched limit dextrin and a maltotetraose. This compound can also be incorporated into the cytoplasm through a maltose ABC transporter. The maltotetraose interacts with a phosphate through a maltodextrin phosphorylase releasing a alpha-D-glucose-1-phosphate and a maltotriose. The maltotriose can also be incorporated through a maltose ABC transporter. The maltotriose can then interact with water through a maltodextrin glucosidase resulting in a D-glucose and a D-maltose. D-maltose can also be incorporated through a maltose ABC transporter The D-maltose can then interact with a maltotriose through a amylomaltase resulting in a maltotetraose and a D-glucose. The D-glucose is then phosphorylated through an ATP driven glucokinase resulting in a hydrogen ion, an ADP and a Beta-D-glucose 6-phosphate PW000941 ec00500 Metabolic Glycolysis / Gluconeogenesis ec00010 Fructose and mannose metabolism ec00051 Amino sugar and nucleotide sugar metabolism ec00520 Microbial metabolism in diverse environments ec01120 Pentose Phosphate PW000893 Metabolic colanic acid building blocks biosynthesis The colonic acid building blocks biosynthesis starts with a Beta-D-Glucose undergoing a transport reaction mediated by a glucose PTS permease. The permease phosphorylates the Beta-D-Glucose, producing a Beta-D-Glucose 6-phosphate. This compound can either change to an Alpha-D-Glucose 6-phosphate spontaneously or into a fructose 6-phosphate through a glucose-6-phosphate isomerase. The latter compound can also be present in E.coli through the interaction of D-fructose and a mannose PTS permease which phosphorylate the D-fructose. Fructose 6-phosphate interacts in a reversible reaction with mannose-6-phosphate isomerase in order to produce a Alpha-D-mannose 6-phosphate. This compound can also be present in E.coli through the interaction of Alpha-D-mannose and a mannose PTS permease which phosphorylates the alpha-D-mannose. Alpha-D-mannose 6-phosphate interacts in a reversible reaction with a phosphomannomutase to produce a alpha-D-mannose 1-phosphate. This compound in turn with a hydrogen ion and gtp undergoes a reaction with a mannose-1-phosphate guanylyltransferase, releasing a pyrophosphate and producing a guanosine diphosphate mannose. Guanosine diphosphate mannose interacts with gdp-mannose 4,6-dehydratase releasing a water, and gdp-4-dehydro-6-deoxy-D-mannose. This compound in turn with hydrogen ion and NADPH interact with GDP-L-fucose synthase releasing NADP and producing a GDP-L-fucose. The Alpha-D-Glucose 6-phosphate interacts in a reversible reaction with phosphoglucomutase-1 to produce a alpha-D-glucose 1-phosphate. This in turn with UTP and hydrogen ion interact with UTP--glucose-1-phosphate uridyleltransferase releasing a pyrophosphate and UDP-glucose. UDP-glucose can either interact with galactose-1-phosphate uridylyltransferase to produce a UDP-galactose or in turn with NAD and water interact with UDP-glucose 6-dehydrogenase releasing a NADH and a hydrogen ion and producing a UDP-glucuronate. GDP-L-fucose, UDP-glucose, UDP-galactose and UDP-glucuronate are sugars that need to be activated in the form of nucleotide sugar prior to their assembly into colanic acid, also known as M antigen. Colanic acid is an extracellular polysaccharide which has been linked to a cluster of 19 genes(wca). PW000951 Metabolic D-sorbitol degradation II Of the six existing hexitols only three (D-mannitol, D-sorbitol [glucitol], and galactitol [owing to symmetry, D- and L-galactitol are identical]) occur naturally and each of these can be utilized by E. coli K-12 as a total source of carbon and energy. Each enters the cell via a specific phosphotransferase system so the first intracellular species is the 6-phospho derivative. D-sorbitol-6-phosphate is converted by a single dehydrogenase reaction to the glycolytic intermediate, D-fructose-6-phosphate and hence flows through the pathways of central metabolism to satisfy the cell's need for precursor metabolites, reducing power, and metabolic energy. PW002022 Metabolic <i>N</i>-acetylglucosamine degradation I GLUAMCAT-PWY gluconeogenesis I GLUCONEO-PWY glycolysis I GLYCOLYSIS mannitol degradation I MANNIDEG-PWY sorbitol degradation II SORBDEG-PWY pentose phosphate pathway (non-oxidative branch) NONOXIPENT-PWY UDP-<i>N</i>-acetyl-D-glucosamine biosynthesis I UDPNAGSYN-PWY D-allose degradation PWY0-44 GDP-mannose biosynthesis PWY-5659 D-mannose degradation MANNCAT-PWY Specdb::CMs 3157 Specdb::CMs 30781 Specdb::CMs 38680 Specdb::CMs 99831 Specdb::CMs 147238 Specdb::NmrOneD 35262 Specdb::NmrOneD 35263 Specdb::NmrOneD 35264 Specdb::NmrOneD 35265 Specdb::NmrOneD 35266 Specdb::NmrOneD 35267 Specdb::NmrOneD 35268 Specdb::NmrOneD 35269 Specdb::NmrOneD 35270 Specdb::NmrOneD 35271 Specdb::NmrOneD 35272 Specdb::NmrOneD 35273 Specdb::NmrOneD 35274 Specdb::NmrOneD 35275 Specdb::NmrOneD 35276 Specdb::NmrOneD 35277 Specdb::NmrOneD 35278 Specdb::NmrOneD 35279 Specdb::NmrOneD 35280 Specdb::NmrOneD 35281 Specdb::MsMs 23189 Specdb::MsMs 23190 Specdb::MsMs 23191 Specdb::MsMs 29987 Specdb::MsMs 29988 Specdb::MsMs 29989 Specdb::MsMs 438854 Specdb::MsMs 438855 Specdb::MsMs 438856 Specdb::MsMs 2339946 Specdb::MsMs 2339947 Specdb::MsMs 2339948 Specdb::MsMs 2626412 Specdb::MsMs 2626413 Specdb::MsMs 2626414 HMDB03971 440641 389526 C05345 16084 FRUCTOSE-6P F6P 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 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Roberts NB, Dutton J, Helliwell T, Rothwell PJ, Kavanagh JP: Pyrophosphate in synovial fluid and urine and its relationship to urinary risk factors for stone disease. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):529-34. 1332571 Sanchez B, Champomier-Verges MC, Anglade P, Baraige F, de Los Reyes-Gavilan CG, Margolles A, Zagorec M: Proteomic analysis of global changes in protein expression during bile salt exposure of Bifidobacterium longum NCIMB 8809. J Bacteriol. 2005 Aug;187(16):5799-808. 16077128 Gagnon M, Kheadr EE, Le Blay G, Fliss I: In vitro inhibition of Escherichia coli O157:H7 by bifidobacterial strains of human origin. Int J Food Microbiol. 2004 Apr 1;92(1):69-78. 15033269 Mannose-6-phosphate isomerase P00946 MANA_ECOLI manA http://ecmdb.ca/proteins/P00946.xml Sorbitol-6-phosphate 2-dehydrogenase P05707 SRLD_ECOLI srlD http://ecmdb.ca/proteins/P05707.xml 6-phosphofructokinase isozyme 2 P06999 K6PF2_ECOLI pfkB http://ecmdb.ca/proteins/P06999.xml Mannitol-1-phosphate 5-dehydrogenase P09424 MTLD_ECOLI mtlD http://ecmdb.ca/proteins/P09424.xml Glucose-6-phosphate isomerase P0A6T1 G6PI_ECOLI pgi http://ecmdb.ca/proteins/P0A6T1.xml 6-phosphofructokinase isozyme 1 P0A796 K6PF1_ECOLI pfkA http://ecmdb.ca/proteins/P0A796.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-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 Fructokinase P23917 MAK_ECOLI mak http://ecmdb.ca/proteins/P23917.xml Transketolase 1 P27302 TKT1_ECOLI tktA http://ecmdb.ca/proteins/P27302.xml D-allulose-6-phosphate 3-epimerase P32719 ALSE_ECOLI alsE http://ecmdb.ca/proteins/P32719.xml Transketolase 2 P33570 TKT2_ECOLI tktB http://ecmdb.ca/proteins/P33570.xml Adenosine triphosphate + D-Fructose <> ADP + beta-D-Fructose 6-phosphate R00867 Mannose 6-phosphate <> beta-D-Fructose 6-phosphate R01819 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 Sorbitol-6-phosphate + NAD <> beta-D-Fructose 6-phosphate + NADH + Hydrogen ion R05607 Glucose 6-phosphate <> beta-D-Fructose 6-phosphate R02740 beta-D-Glucose 6-phosphate <> beta-D-Fructose 6-phosphate R03321 Adenosine triphosphate + beta-D-Fructose <> ADP + beta-D-Fructose 6-phosphate R03920 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 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 beta-D-Glucose 6-phosphate > beta-D-Fructose 6-phosphate PW_R003448 Sorbitol-6-phosphate + NAD <> beta-D-Fructose 6-phosphate + NADH + Hydrogen ion Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + beta-D-Fructose 6-phosphate Glucose 6-phosphate <> beta-D-Fructose 6-phosphate Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Erythrose 4-phosphate + beta-D-Fructose 6-phosphate 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 55.1 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 220400 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776