2.02012-05-31 14:30:03 -06002015-06-03 17:19:24 -0600ECMDB20149M2MDB000996Galactitol 1-phosphateGalactitol 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. 1-O-Phosphono-D-galactitolD-Galactitol 1-(dihydrogen phosphate)D-Galactitol 1-(dihydrogen phosphoric acid)D-Galactitol 1-phosphateD-Galactitol 1-phosphoric acidGalactitol 1-phosphoric acidGalactitol-1-phosphateGalactitol-1-phosphoric acidGalactitol1PL-Galactitol 6-phosphateL-Galactitol 6-phosphoric acidC6H15O9P262.1517262.04536859{[(2S,3R,4S,5R)-2,3,4,5,6-pentahydroxyhexyl]oxy}phosphonic acidgalactitol 1-phosphate15664-55-8[H][C@@](O)(CO)[C@]([H])(O)[C@]([H])(O)[C@@]([H])(O)COP(O)(O)=OInChI=1S/C6H15O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3-11H,1-2H2,(H2,12,13,14)/t3-,4+,5+,6-/m1/s1GACTWZZMVMUKNG-DPYQTVNSSA-NCytosollogp-2.32logs-0.99solubility2.66e+01 g/llogp-3.9pka_strongest_acidic1.49pka_strongest_basic-3iupac{[(2S,3R,4S,5R)-2,3,4,5,6-pentahydroxyhexyl]oxy}phosphonic acidaverage_mass262.1517mono_mass262.04536859smiles[H][C@@](O)(CO)[C@]([H])(O)[C@]([H])(O)[C@@]([H])(O)COP(O)(O)=OformulaC6H15O9PinchiInChI=1S/C6H15O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3-11H,1-2H2,(H2,12,13,14)/t3-,4+,5+,6-/m1/s1inchikeyGACTWZZMVMUKNG-DPYQTVNSSA-Npolar_surface_area167.91refractivity49.28polarizability21.61rotatable_bond_count7acceptor_count8donor_count7physiological_charge-2formal_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
PW000821ec00052MetabolicPhosphotransferase system (PTS)ec02060Metabolic pathwayseco01100galactitol degradationGALACTITOLCAT-PWYSpecdb::CMs1083329Specdb::NmrOneD314601Specdb::NmrOneD314602Specdb::NmrOneD314603Specdb::NmrOneD314604Specdb::NmrOneD314605Specdb::NmrOneD314606Specdb::NmrOneD314607Specdb::NmrOneD314608Specdb::NmrOneD314609Specdb::NmrOneD314610Specdb::NmrOneD314611Specdb::NmrOneD314612Specdb::NmrOneD314613Specdb::NmrOneD314614Specdb::NmrOneD314615Specdb::NmrOneD314616Specdb::NmrOneD314617Specdb::NmrOneD314618Specdb::NmrOneD314619Specdb::NmrOneD314620Specdb::MsMs23024Specdb::MsMs23025Specdb::MsMs23026Specdb::MsMs29822Specdb::MsMs29823Specdb::MsMs29824440969389796C0631128663GALACTITOL-1-PHOSPHATEKeseler, 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-D114.22080510van 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 370:17-25.17765195Phosphoenolpyruvate-protein phosphotransferaseP08839PT1_ECOLIptsIhttp://ecmdb.ca/proteins/P08839.xmlGalactitol-1-phosphate 5-dehydrogenaseP0A9S3GATD_ECOLIgatDhttp://ecmdb.ca/proteins/P0A9S3.xmlGalactitol-specific phosphotransferase enzyme IIB componentP37188PTKB_ECOLIgatBhttp://ecmdb.ca/proteins/P37188.xmlPutative phosphotransferase IIA component sgcAP39363SGCA_ECOLIsgcAhttp://ecmdb.ca/proteins/P39363.xmlPutative phosphotransferase enzyme IIB component sgcBP58035SGCB_ECOLIsgcBhttp://ecmdb.ca/proteins/P58035.xmlGalactitol-specific phosphotransferase enzyme IIA componentP69828PTKA_ECOLIgatAhttp://ecmdb.ca/proteins/P69828.xmlPutative permease IIC componentP39365SGCC_ECOLIsgcChttp://ecmdb.ca/proteins/P39365.xmlGalactitol permease IIC componentP69831PTKC_ECOLIgatChttp://ecmdb.ca/proteins/P69831.xmlPhosphocarrier protein HPrP0AA04PTHP_ECOLIptsHhttp://ecmdb.ca/proteins/P0AA04.xmlGalactitol permease IIC componentP69831PTKC_ECOLIgatChttp://ecmdb.ca/proteins/P69831.xmlPhosphoenolpyruvic acid + Galactitol > Galactitol 1-phosphate + Pyruvic acidTRANS-RXN-161Galactitol 1-phosphate + NAD <> Hydrogen ion + NADH + D-Tagatose 6-phosphateR05571GALACTITOLPDEHYD-RXNGalactitol + Protein N(pi)-phospho-L-histidine <> Galactitol 1-phosphate + Protein histidineR05570Phosphoenolpyruvic acid + Galactitol > Galactitol 1-phosphate + Pyruvic acidTRANS-RXN-161Galactitol 1-phosphate + NAD > L-Tagatose-6-phosphate + NADHNAD + Galactitol 1-phosphate <> L-Tagatose-6-phosphate + NADH + Hydrogen ionR05147 Galactitol + Protein N(pi)-phospho-L-histidine <> Galactitol 1-phosphate + Protein histidineGalactitol + Protein N(pi)-phospho-L-histidine <> Galactitol 1-phosphate + Protein histidine