2.0 2012-05-31 09:57:27 -0600 2015-06-03 15:53:12 -0600 ECMDB00107 M2MDB000040 Galactitol Galactitol, also called dulcitol, is a sugar alcohol, the reduction product of galactose. Galactitol is produced from galactose in a reaction catalyzed by aldose reductase. Galactose itself comes from the metabolism of the disaccharide lactose into glucose and galactose (Wikipedia). It appears as a white crystalline powder with a slight sweet taste. Ambap5938 D-Dulcitol Dulcite Dulcitol Dulcose Euonymit Galactitol Hexitol Melampyrin Melampyrit Melampyrite Melampyrum Meso-galactitol C6H14O6 182.1718 182.07903818 (2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol galactitol 608-66-2 OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6- FBPFZTCFMRRESA-GUCUJZIJSA-N Solid Extra-organism Periplasm logp -2.68 ALOGPS logs 0.10 ALOGPS solubility 2.29e+02 g/l ALOGPS melting_point 189.5 oC logp -3.7 ChemAxon pka_strongest_acidic 12.59 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol ChemAxon average_mass 182.1718 ChemAxon mono_mass 182.07903818 ChemAxon smiles OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO ChemAxon formula C6H14O6 ChemAxon inchi InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6- ChemAxon inchikey FBPFZTCFMRRESA-GUCUJZIJSA-N ChemAxon polar_surface_area 121.38 ChemAxon refractivity 38.4 ChemAxon polarizability 17.25 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Galactose metabolism Galactose 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 PW000821 ec00052 Metabolic Phosphotransferase system (PTS) ec02060 Galactitol and galactonate degradation D-galactonate can serve as the sole source of carbon and energy for E. coli . The initial step, after the transport of galactonic acid into the cell is the degradation of D-galactonate is dehydration to 2-dehydro-3-deoxy-D-galactonate by D-galactonate dehydratase. Subsequent phosphorylation by 2-dehydro-3-deoxygalactonate kinase and aldol cleavage by 2-oxo-3-deoxygalactonate 6-phosphate aldolase produce pyruvate and D-glyceraldehyde-3-phosphate, which enter central metabolism. Galactitol can also 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 D-galactitol-1-phosphate or D-galactitol-6-phosphate, which are identical. This sugar alcohol phosphate becomes the substrate for a dehydrogenase that oxidizes its 2-alcohol group to a keto group. Galactitol-1-phosphate, the product of the dehydrogenation is tagatose-6-phosphate, which becomes the substrate of a kinase and subsequently an aldolase (in a pair of reactions that parallel those of glycolysis) before it is converted into intermediates (D-glyceraldehde-3-phosphate and dihydroxy-acetone-phosphate) of glycolysis. PW000820 Metabolic Specdb::CMs 323 Specdb::CMs 1668 Specdb::CMs 9726 Specdb::CMs 30543 Specdb::CMs 30999 Specdb::CMs 37296 Specdb::CMs 132330 Specdb::CMs 140064 Specdb::CMs 1050073 Specdb::CMs 1050075 Specdb::CMs 1050077 Specdb::CMs 1050079 Specdb::CMs 1050080 Specdb::CMs 1050082 Specdb::CMs 1050084 Specdb::CMs 1050086 Specdb::CMs 1050087 Specdb::CMs 1050089 Specdb::CMs 1050091 Specdb::CMs 1050092 Specdb::CMs 1050094 Specdb::CMs 1050096 Specdb::CMs 1050098 Specdb::CMs 1050100 Specdb::CMs 1050101 Specdb::NmrOneD 1086 Specdb::NmrOneD 1147 Specdb::NmrOneD 142230 Specdb::NmrOneD 142231 Specdb::NmrOneD 142232 Specdb::NmrOneD 142233 Specdb::NmrOneD 142234 Specdb::NmrOneD 142235 Specdb::NmrOneD 142236 Specdb::NmrOneD 142237 Specdb::NmrOneD 142238 Specdb::NmrOneD 142239 Specdb::NmrOneD 142240 Specdb::NmrOneD 142241 Specdb::NmrOneD 142242 Specdb::NmrOneD 142243 Specdb::NmrOneD 142244 Specdb::NmrOneD 142245 Specdb::NmrOneD 142246 Specdb::NmrOneD 142247 Specdb::NmrOneD 142248 Specdb::NmrOneD 142249 Specdb::NmrOneD 166477 Specdb::MsMs 159 Specdb::MsMs 160 Specdb::MsMs 161 Specdb::MsMs 287461 Specdb::MsMs 287462 Specdb::MsMs 287463 Specdb::MsMs 326326 Specdb::MsMs 326327 Specdb::MsMs 326328 Specdb::MsMs 1470891 Specdb::MsMs 1470892 Specdb::MsMs 1470893 Specdb::MsMs 1471266 Specdb::MsMs 1471267 Specdb::MsMs 1471268 Specdb::MsMs 1471269 Specdb::MsMs 1471270 Specdb::MsMs 1472395 Specdb::MsMs 1472396 Specdb::MsMs 1472397 Specdb::MsMs 1472398 Specdb::MsMs 1472399 Specdb::MsMs 1472400 Specdb::MsMs 1472401 Specdb::MsMs 1472402 Specdb::NmrTwoD 1144 HMDB00107 11850 11357 C01697 16813 GALACTITOL Galactitol 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." 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Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Galactitol-specific phosphotransferase enzyme IIB component P37188 PTKB_ECOLI gatB http://ecmdb.ca/proteins/P37188.xml Putative phosphotransferase IIA component sgcA P39363 SGCA_ECOLI sgcA http://ecmdb.ca/proteins/P39363.xml Putative phosphotransferase enzyme IIB component sgcB P58035 SGCB_ECOLI sgcB http://ecmdb.ca/proteins/P58035.xml Galactitol-specific phosphotransferase enzyme IIA component P69828 PTKA_ECOLI gatA http://ecmdb.ca/proteins/P69828.xml Putative permease IIC component P39365 SGCC_ECOLI sgcC http://ecmdb.ca/proteins/P39365.xml Galactitol permease IIC component P69831 PTKC_ECOLI gatC http://ecmdb.ca/proteins/P69831.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml Galactitol permease IIC component P69831 PTKC_ECOLI gatC http://ecmdb.ca/proteins/P69831.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Phosphoenolpyruvic acid + Galactitol > Galactitol 1-phosphate + Pyruvic acid TRANS-RXN-161 Galactitol + Protein N(pi)-phospho-L-histidine <> Galactitol 1-phosphate + Protein histidine R05570 Phosphoenolpyruvic acid + Galactitol > Galactitol 1-phosphate + Pyruvic acid TRANS-RXN-161 Galactitol + HPr - phosphorylated > Galactose 1-phosphate + HPr + Galactose 1-phosphate PW_RCT000113 Galactitol + Protein N(pi)-phospho-L-histidine <> Galactitol 1-phosphate + Protein histidine Galactitol + Protein N(pi)-phospho-L-histidine <> Galactitol 1-phosphate + Protein histidine