2.02012-05-31 10:22:20 -06002015-06-03 15:53:20 -0600ECMDB00160M2MDB000062InositolInositol or cyclohexane-1,2,3,4,5,6-hexol is a chemical compound with formula C6H12O6 or (-CHOH-)6, a six-fold alcohol (polyol) of cyclohexane. It exists in nine possible stereoisomers, of which the most prominent form, widely occuring in nature, is cis-1,2,3,5-trans-4,6-cyclohexanehexol, or myo-inositol. Other naturally occurring isomers (though in minimal quantities) are scyllo-, muco-, D-chiro-, and neo-inositol. The other possible isomers are L-chiro-, allo-, epi-, and cis-inositol. (Wikipedia)(1a,2a,3a,4b,5a,6b)1,2,3,4,5,6-Cyclohexanehexol(1alpha,2alpha,3alpha,4beta,5alpha,6beta)1,2,3,4,5,6-cyclohexanehexol(1r,2R,3S,4s,5R,6S)-cyclohexane-1,2,3,4,5,6-hexol(1α,2α,3α,4β,5α,6β)1,2,3,4,5,6-Cyclohexanehexol1,2,3,4,5, 6-Cyclohexanehexol1,2,3,4,5,6-Cyclohexanehexol1,2,3,4,5,6-cyclohexanehexol (ACD/Name 4.0)1,2,3,4,5,6-HEXAHYDROXY-CYCLOHEXANE1,2,3,5/4,6-Cyclohexanehexol1,2,3,5/4,6-Hexahydroxycyclohexane1D-Myo-Inositol1L-Myo-Inositol<i>meso</i>-inositolBios iChiro-inositolCis-1,2,3,5-trans-4,6-CyclohexanehexolCyclohexanehexolCyclohexitolD-Myo-InositolDamboseHexahydroxycyclohexaneI-InositolInositInositalInositeInositeneInositinaInositolINOSITOL (D)Inositol (DCF)InsIso-InositolL-Myo-InositolM-InositolMalt extractMeat sugarMeso-InositolMesoinositMesoinositeMesoinositolMesolMesovitMIMouse antialopecia factorMuscle sugarMyo-InositolMyoinositeMyoinositolNucitePhaseomannitePhaseomannitolRat antispectacled eye factorScylliteC6H12O6180.1559180.063388116cyclohexane-1,2,3,4,5,6-hexol(-)-inositol6917-35-7OC1C(O)C(O)C(O)C(O)C1OInChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12HCDAISMWEOUEBRE-UHFFFAOYSA-NSolidCytosolExtra-organismPeriplasmlogp-2.59logs0.43solubility4.85e+02 g/lmelting_point224-227 oClogp-3.8pka_strongest_acidic12.29pka_strongest_basic-3.6iupaccyclohexane-1,2,3,4,5,6-hexolaverage_mass180.1559mono_mass180.063388116smilesOC1C(O)C(O)C(O)C(O)C1OformulaC6H12O6inchiInChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12HinchikeyCDAISMWEOUEBRE-UHFFFAOYSA-Npolar_surface_area121.38refractivity35.77polarizability16.13rotatable_bond_count0acceptor_count6donor_count6physiological_charge0formal_charge0Galactose 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
PW000821ec00052MetabolicAscorbate and aldarate metabolismec00053Inositol phosphate metabolismec00562Streptomycin biosynthesisec00521Microbial metabolism in diverse environmentsec01120Metabolic pathwayseco01100Specdb::CMs80388Specdb::EiMs1880Specdb::NmrOneD3992Specdb::NmrOneD4278Specdb::MsMs20252Specdb::MsMs20253Specdb::MsMs20254Specdb::MsMs21242Specdb::MsMs21243Specdb::MsMs21244Specdb::MsMs21803Specdb::MsMs21804Specdb::MsMs21805Specdb::MsMs22793Specdb::MsMs22794Specdb::MsMs22795HMDB13777868C0013717268MYO-INOSITOLInositolKeseler, 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). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, 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 80:2939-2948.18331064Bennett, 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 5:593-599.19561621Alpha-galactosidaseP06720AGAL_ECOLImelAhttp://ecmdb.ca/proteins/P06720.xmlPeriplasmic AppA proteinP07102PPA_ECOLIappAhttp://ecmdb.ca/proteins/P07102.xmlGlycerophosphoryl diester phosphodiesteraseP09394GLPQ_ECOLIglpQhttp://ecmdb.ca/proteins/P09394.xmlInositol-1-monophosphataseP0ADG4SUHB_ECOLIsuhBhttp://ecmdb.ca/proteins/P0ADG4.xmlGlycerophosphoryl diester phosphodiesterase_P10908UGPQ_ECOLIugpQhttp://ecmdb.ca/proteins/P10908.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlUncharacterized symporter yidKP31448YIDK_ECOLIyidKhttp://ecmdb.ca/proteins/P31448.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xml6 Water + Myo-inositol hexakisphosphate > Inositol +6 PhosphateSn-Glycero-3-phospho-1-inositol + Water > Glycerol 3-phosphate + Hydrogen ion + InositolWater + Myo-inositol 1-phosphate > Inositol + PhosphateR01185Myo-inositol 1-phosphate + Water <> Inositol + PhosphateR01185D-Myo-inositol 4-phosphate + Water <> Inositol + PhosphateR011861D-myo-Inositol 3-phosphate + Water <> Inositol + PhosphateR01187Galactinol + Water <> Inositol + D-GalactoseR01194Water + D-Myo-inositol (1)-monophosphate > Phosphate + InositolRXN0-5408myo-Inositol phosphate + Water <> Inositol + PhosphateR07343 Water + Myo-inositol 1-phosphate > Inositol + PhosphateWater + Myo-inositol 1-phosphate > Inositol + PhosphateGutnick 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 glucoseShake flask and filter culture5.72uM0.037 oCK12 NCM3722Mid-Log Phase228800Bennett, 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 5:593-599.19561621Gutnick 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 glycerolShake flask and filter culture7.05uM0.037 oCK12 NCM3722Mid-Log Phase282000Bennett, 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 5:593-599.19561621Gutnick 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 acetateShake flask and filter culture6.9uM0.037 oCK12 NCM3722Mid-Log Phase276000Bennett, 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