2.0 2012-10-10 12:14:40 -0600 2015-06-03 17:25:51 -0600 ECMDB23065 M2MDB003455 L-Tagatose-6-phosphate L-Tagatose-6-phosphate is a substrate for galactitol-1-phosphate 5-dehydrogenase. Specifically this enzyme converts galactitol 1-phosphate to tagatose 6-phosphate. Galactitol (dulcitol) is a sugar alcohol and is actually the reduction product of galactose. L-tagatose 6-phosphate is an intermediate in galactose metabolism Tagatose is a naturally occurring monosaccharide, specifically a hexose. It is often found in dairy products, and is very similar in texture to sucrose (table sugar). E. coli can use tagatose and galactose as a carbon source. (2S,3S,4R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-ylmethyl dihydrogen phosphate (2S,3S,4R)-3,4,5-Trihydroxy-5-(hydroxymethyl)oxolan-2-ylmethyl dihydrogen phosphoric acid 6-O-Phosphono-L-tagatofuranose L-Tagatose 6-phosphate L-Tagatose 6-phosphoric acid L-Tagatose-6-phosphoric acid C6H13O9P 260.1358 260.029718526 {[(2S,3S,4R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid L-tagatose 6-phosphate [H][C@@]1(O)[C@]([H])(COP(O)(O)=O)OC(O)(CO)[C@]1([H])O 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?/m0/s1 BGWGXPAPYGQALX-JMSAOHGTSA-N 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 {[(2S,3S,4R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 260.1358 ChemAxon mono_mass 260.029718526 ChemAxon smiles [H][C@@]1(O)[C@]([H])(COP(O)(O)=O)OC(O)(CO)[C@]1([H])O 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?/m0/s1 ChemAxon inchikey BGWGXPAPYGQALX-JMSAOHGTSA-N ChemAxon polar_surface_area 156.91 ChemAxon refractivity 47.23 ChemAxon polarizability 20.8 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -2 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 Metabolic pathways eco01100 Specdb::CMs 1084667 Specdb::NmrOneD 303171 Specdb::NmrOneD 303172 Specdb::NmrOneD 303173 Specdb::NmrOneD 303174 Specdb::NmrOneD 303175 Specdb::NmrOneD 303176 Specdb::NmrOneD 303177 Specdb::NmrOneD 303178 Specdb::NmrOneD 303179 Specdb::NmrOneD 303180 Specdb::NmrOneD 303181 Specdb::NmrOneD 303182 Specdb::NmrOneD 303183 Specdb::NmrOneD 303184 Specdb::NmrOneD 303185 Specdb::NmrOneD 303186 Specdb::NmrOneD 303187 Specdb::NmrOneD 303188 Specdb::NmrOneD 303189 Specdb::NmrOneD 303190 Specdb::MsMs 27176 Specdb::MsMs 27177 Specdb::MsMs 27178 Specdb::MsMs 33734 Specdb::MsMs 33735 Specdb::MsMs 33736 C06312 Galactitol-1-phosphate 5-dehydrogenase P0A9S3 GATD_ECOLI gatD http://ecmdb.ca/proteins/P0A9S3.xml Galactitol 1-phosphate + NAD > L-Tagatose-6-phosphate + NADH NAD + Galactitol 1-phosphate <> L-Tagatose-6-phosphate + NADH + Hydrogen ion R05147