2.02012-05-31 10:25:06 -06002015-09-13 12:56:07 -0600ECMDB00258M2MDB000109SucroseSucrose is a nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. Sucrose can be used as a carbon/energy substrate by E. coli. The sucrose porin (ScrY) which resides in the bacterial outer membrane facilitate the passive diffusion of sucrose into the cell. Sucrose metabolism is controlled by the csc regulon. The csc regulon comprises three genes for a sucrose permease, a fructokinase, and a sucrose hydrolase (genes cscB, cscK, and cscA, respectively).α-D-glucopyranosyl β-D-fructofuranoside(+)-Sucrosea-D-Glucopyranosyl b-D-fructofuranosideAlpha-D-Glucopyranosyl beta-D-fructofuranosideB -D-Fructofuranosyl a-D-glucopyranosideD-(+)-SaccharoseD-(+)-SucroseD-SucroseGlc(α1->2β)FruGLC(a1->2b)fruGlc(alpha1->2beta)FruGLC(α1->2β)fruSaccharoseSaccharumSucroseSugarTable sugarWhite sugarα-D-Glucopyranosyl β-D-fructofuranosideC12H22O11342.2965342.116211546(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triolsucrose57-50-1OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1OInChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1CZMRCDWAGMRECN-UGDNZRGBSA-NSolidExtra-organismPeriplasmlogp-2.63logs0.38solubility8.24e+02 g/lmelting_point185.5 oClogp-4.5pka_strongest_acidic11.84pka_strongest_basic-3iupac(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triolaverage_mass342.2965mono_mass342.116211546smilesOC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1OformulaC12H22O11inchiInChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1inchikeyCZMRCDWAGMRECN-UGDNZRGBSA-Npolar_surface_area189.53refractivity68.77polarizability31.04rotatable_bond_count5acceptor_count11donor_count8physiological_charge0formal_charge0Starch and sucrose metabolismThe 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-phosphatePW000941ec00500MetabolicGalactose metabolismGalactose can be synthesized through two pathways: melibiose degradation involving an alpha galactosidase and lactose degradation involving a beta galactosidase. Melibiose is first transported inside the cell through the melibiose:Li+/Na+/H+ symporter. Once inside the cell, melibiose is degraded through alpha galactosidase into an alpha-D-galactose and a beta-D-glucose. The beta-D-glucose is phosphorylated by a glucokinase to produce a beta-D-glucose-6-phosphate which can spontaneously be turned into a alpha D glucose 6 phosphate. This alpha D-glucose-6-phosphate is metabolized into a glucose -1-phosphate through a phosphoglucomutase-1. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase.
Galactose can also be produced by lactose degradation involving a lactose permease to uptake lactose from the environment and a beta-galactosidase to turn lactose into Beta-D-galactose.
Beta-D-galactose can also be uptaken from the environment through a galactose proton symporter.
Galactose is degraded through the following process:
Beta-D-galactose is introduced into the cytoplasm through a galactose proton symporter, or it can be synthesized from an alpha lactose that is introduced into the cytoplasm through a lactose permease. Alpha lactose interacts with water through a beta-galactosidase resulting in a beta-D-glucose and beta-D-galactose. Beta-D-galactose is isomerized into D-galactose. D-Galactose undergoes phosphorylation through a galactokinase, hence producing galactose 1 phosphate. On the other side of the pathway, a gluose-1-phosphate (product of the interaction of alpha-D-glucose 6-phosphate with a phosphoglucomutase resulting in a alpha-D-glucose-1-phosphate, an isomer of Glucose 1-phosphate, or an isomer of Beta-D-glucose 1-phosphate) interacts with UTP and a hydrogen ion in order to produce a uridine diphosphate glucose. This is followed by the interaction of galactose-1-phosphate with an established amount of uridine diphosphate glucose through a galactose-1-phosphate uridylyltransferase, which in turn output a glucose-1-phosphate and a uridine diphosphate galactose. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase, and so the cycle can keep going as long as more lactose or galactose is imported into the cell
PW000821ec00052MetabolicPhosphotransferase system (PTS)ec02060ABC transportersec02010Specdb::CMs493Specdb::CMs494Specdb::CMs495Specdb::CMs15318Specdb::CMs30233Specdb::CMs30697Specdb::CMs30774Specdb::CMs31787Specdb::CMs37389Specdb::CMs137266Specdb::CMs145000Specdb::CMs1055594Specdb::CMs1055596Specdb::CMs1055598Specdb::CMs1055600Specdb::CMs1055602Specdb::CMs1055604Specdb::CMs1055606Specdb::CMs1055608Specdb::CMs1055610Specdb::CMs1055611Specdb::CMs1055613Specdb::CMs1055615Specdb::CMs1055617Specdb::CMs1055619Specdb::EiMs1756Specdb::NmrOneD1220Specdb::NmrOneD1293Specdb::NmrOneD3910Specdb::NmrOneD4186Specdb::NmrOneD4996Specdb::NmrOneD166519Specdb::MsMs448Specdb::MsMs449Specdb::MsMs450Specdb::MsMs3790Specdb::MsMs178587Specdb::MsMs178588Specdb::MsMs178589Specdb::MsMs180906Specdb::MsMs180907Specdb::MsMs180908Specdb::MsMs439024Specdb::MsMs2227157Specdb::MsMs2227566Specdb::MsMs2234291Specdb::MsMs2236230Specdb::MsMs2237135Specdb::MsMs2238398Specdb::MsMs2239203Specdb::MsMs2240377Specdb::MsMs2241307Specdb::MsMs2242436Specdb::MsMs2243439Specdb::MsMs2248756Specdb::MsMs2249642Specdb::MsMs2253031Specdb::NmrTwoD1009Specdb::NmrTwoD1243HMDB0025859885768C0008917992SUCROSESUCSucroseKeseler, 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-D114.22080510Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72.18402659van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). 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Tetrahedron Letters (2007), 48(23), 4111-4114.http://hmdb.ca/system/metabolites/msds/000/000/190/original/HMDB00258.pdf?1358895907PTS system mannitol-specific EIICBA componentP00550PTM3C_ECOLImtlAhttp://ecmdb.ca/proteins/P00550.xmlAlpha-galactosidaseP06720AGAL_ECOLImelAhttp://ecmdb.ca/proteins/P06720.xmlPTS system beta-glucoside-specific EIIBCA componentP08722PTV3B_ECOLIbglFhttp://ecmdb.ca/proteins/P08722.xmlPhosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlPTS system N-acetylglucosamine-specific EIICBA componentP09323PTW3C_ECOLInagEhttp://ecmdb.ca/proteins/P09323.xmlPhosphatase yidAP0A8Y5YIDA_ECOLIyidAhttp://ecmdb.ca/proteins/P0A8Y5.xmlPTS system maltose- and glucose-specific EIICB componentP19642PTOCB_ECOLImalXhttp://ecmdb.ca/proteins/P19642.xmlPTS system fructose-specific EIIBC componentP20966PTFBC_ECOLIfruAhttp://ecmdb.ca/proteins/P20966.xmlMaltodextrin glucosidaseP21517MALZ_ECOLImalZhttp://ecmdb.ca/proteins/P21517.xmlPTS system arbutin-, cellobiose-, and salicin-specific EIIBC componentP24241PTIBC_ECOLIascFhttp://ecmdb.ca/proteins/P24241.xmlAlpha-glucosidase yihQP32138YIHQ_ECOLIyihQhttp://ecmdb.ca/proteins/P32138.xmlFructose-like PTS system EIIBC componentP32154PTFLB_ECOLIfrvBhttp://ecmdb.ca/proteins/P32154.xmlFructose-like phosphotransferase enzyme IIB component 3P32676PTFB3_ECOLIfrwDhttp://ecmdb.ca/proteins/P32676.xmlPTS system trehalose-specific EIIBC componentP36672PTTBC_ECOLItreBhttp://ecmdb.ca/proteins/P36672.xmlGalactitol-specific phosphotransferase enzyme IIB componentP37188PTKB_ECOLIgatBhttp://ecmdb.ca/proteins/P37188.xmlN-acetylgalactosamine-specific phosphotransferase enzyme IIB component 2P42904PTPB2_ECOLIagaVhttp://ecmdb.ca/proteins/P42904.xmlN-acetylgalactosamine-specific phosphotransferase enzyme IIB component 1P42909PTPB1_ECOLIagaBhttp://ecmdb.ca/proteins/P42909.xmlHeat-responsive suppressor hrsAP54745HRSA_ECOLIhrsAhttp://ecmdb.ca/proteins/P54745.xmlGlucitol/sorbitol-specific phosphotransferase enzyme IIB componentP56580PTHB_ECOLIsrlEhttp://ecmdb.ca/proteins/P56580.xmlPutative phosphotransferase enzyme IIB component sgcBP58035SGCB_ECOLIsgcBhttp://ecmdb.ca/proteins/P58035.xmlGlucose-specific phosphotransferase enzyme IIA componentP69783PTGA_ECOLIcrrhttp://ecmdb.ca/proteins/P69783.xmlPTS system glucose-specific EIICB componentP69786PTGCB_ECOLIptsGhttp://ecmdb.ca/proteins/P69786.xmlN,N'-diacetylchitobiose-specific phosphotransferase enzyme IIB componentP69795PTQB_ECOLIchbBhttp://ecmdb.ca/proteins/P69795.xmlPTS system mannose-specific EIIAB componentP69797PTNAB_ECOLImanXhttp://ecmdb.ca/proteins/P69797.xmlFructose-like phosphotransferase enzyme IIB component 1P69808PTFB1_ECOLIfryBhttp://ecmdb.ca/proteins/P69808.xmlFructose-like phosphotransferase enzyme IIB component 2P69816PTFB2_ECOLIfrwBhttp://ecmdb.ca/proteins/P69816.xmlAscorbate-specific phosphotransferase enzyme IIB componentP69822ULAB_ECOLIulaBhttp://ecmdb.ca/proteins/P69822.xmlPTS system mannitol-specific cryptic EIICB componentP69826PTMCB_ECOLIcmtAhttp://ecmdb.ca/proteins/P69826.xmlSugar phosphatase supHP75792SUPH_ECOLIsupHhttp://ecmdb.ca/proteins/P75792.xmlPutative sucrose phosphorylaseP76041SUCP_ECOLIycjMhttp://ecmdb.ca/proteins/P76041.xmlPTS system N-acetylmuramic acid-specific EIIBC componentP77272PTYBC_ECOLImurPhttp://ecmdb.ca/proteins/P77272.xmlUncharacterized protein yigLP27848YIGL_ECOLIyigLhttp://ecmdb.ca/proteins/P27848.xmlPhosphocarrier protein HPrP0AA04PTHP_ECOLIptsHhttp://ecmdb.ca/proteins/P0AA04.xml2-deoxyglucose-6-P phosphataseP77247yniChttp://ecmdb.ca/proteins/P77247.xmlsugar phosphatasP77625yfbThttp://ecmdb.ca/proteins/P77625.xmlPTS system mannitol-specific EIICBA componentP00550PTM3C_ECOLImtlAhttp://ecmdb.ca/proteins/P00550.xmlPTS system beta-glucoside-specific EIIBCA componentP08722PTV3B_ECOLIbglFhttp://ecmdb.ca/proteins/P08722.xmlPTS system N-acetylglucosamine-specific EIICBA componentP09323PTW3C_ECOLInagEhttp://ecmdb.ca/proteins/P09323.xmlPTS system maltose- and glucose-specific EIICB componentP19642PTOCB_ECOLImalXhttp://ecmdb.ca/proteins/P19642.xmlPTS system fructose-specific EIIBC componentP20966PTFBC_ECOLIfruAhttp://ecmdb.ca/proteins/P20966.xmlPTS system arbutin-, cellobiose-, and salicin-specific EIIBC componentP24241PTIBC_ECOLIascFhttp://ecmdb.ca/proteins/P24241.xmlFructose-like PTS system EIIBC componentP32154PTFLB_ECOLIfrvBhttp://ecmdb.ca/proteins/P32154.xmlPTS system trehalose-specific EIIBC componentP36672PTTBC_ECOLItreBhttp://ecmdb.ca/proteins/P36672.xmlPTS system glucose-specific EIICB componentP69786PTGCB_ECOLIptsGhttp://ecmdb.ca/proteins/P69786.xmlPTS system mannitol-specific cryptic EIICB componentP69826PTMCB_ECOLIcmtAhttp://ecmdb.ca/proteins/P69826.xmlPTS system N-acetylmuramic acid-specific EIIBC componentP77272PTYBC_ECOLImurPhttp://ecmdb.ca/proteins/P77272.xmlSugar efflux transporter CP31436SETC_ECOLIsetChttp://ecmdb.ca/proteins/P31436.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlPhosphoenolpyruvic acid + Sucrose > Pyruvic acid + Sucrose-6-phosphateSucrose + Water <> D-Fructose + D-GlucoseR00801Sucrose + Water <> beta-D-Fructose + alpha-D-GlucoseR00802Sucrose + Phosphate <> D-Fructose + Glucose 1-phosphateR00803Raffinose + Water <> D-Galactose + SucroseR01103Protein EIIB N(pi)-phospho-L-histidine/cysteine + Sucrose > protein EIIB + sugar phosphateSucrose + Inorganic phosphate > D-Fructose + Alpha-D-glucose 1-phosphateSugar phosphate + Water > Sucrose + Inorganic phosphateSucrose + Phosphate <> D-Fructose + Glucose 1-phosphateR00803 R06034 Sucrose + Water <> D-Fructose + D-Glucose + D-FructosePW_R003504UDP-Glucose + D-Fructose + D-Fructose <> Sucrose + PhosphatePW_R003518D-Fructose + Alpha-D-glucose 1-phosphate + D-Fructose <> Phosphate + SucrosePW_R003519