2.0 2012-05-31 14:29:40 -0600 2015-06-03 17:19:23 -0600 ECMDB20141 M2MDB000989 D-Galactosamine 6-phosphate D-galactosamine 6-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. D-Galactosamine 6-phosphate is a metabolite in amino sugar catabolism. The GlcNAc6P deacetylase is an enzyme of the amino sugar catabolic pathway that catalyzes the conversion of the GlcNAc6P into glucosamine 6-phosphate (GlcN6P). (PMID 16630633) Glucosamine 6-phosphate (GlcN-6-P) synthase is an ubiquitous enzyme that catalyses the first committed step in the reaction pathway that leads to formation of uridine 5'-diphospho-N-acetyl-D-glucosamine (UDP-GlcNAc), a precursor of macromolecules that contain amino sugars. (PMID 17681543) 2-Amino-2-deoxy-6-O-phosphono-D-galactopyranose 2-Amino-2-deoxy-D-galactopyranose 6-(dihydrogen phosphate) 2-amino-2-Deoxy-D-galactopyranose 6-(dihydrogen phosphoric acid) D-Galactosamine 6-phosphoric acid Glucosamine 6-phosphate Glucosamine 6-phosphoric acid C6H14NO8P 259.151 259.045702941 {[(2R,3R,4R,5R)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid D-galactosamine 6-phosphate [H]C1(O)O[C@]([H])(COP(O)(O)=O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])N InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1 XHMJOUIAFHJHBW-GASJEMHNSA-N Cytoplasm Periplasm logp -2.60 ALOGPS logs -0.87 ALOGPS solubility 3.48e+01 g/l ALOGPS logp -4.2 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic 8.23 ChemAxon iupac {[(2R,3R,4R,5R)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 259.151 ChemAxon mono_mass 259.045702941 ChemAxon smiles [H]C1(O)O[C@]([H])(COP(O)(O)=O)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])N ChemAxon formula C6H14NO8P ChemAxon inchi InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1 ChemAxon inchikey XHMJOUIAFHJHBW-GASJEMHNSA-N ChemAxon polar_surface_area 162.7 ChemAxon refractivity 48.45 ChemAxon polarizability 21.22 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -1 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 Specdb::CMs 1083860 Specdb::NmrOneD 306371 Specdb::NmrOneD 306372 Specdb::NmrOneD 306373 Specdb::NmrOneD 306374 Specdb::NmrOneD 306375 Specdb::NmrOneD 306376 Specdb::NmrOneD 306377 Specdb::NmrOneD 306378 Specdb::NmrOneD 306379 Specdb::NmrOneD 306380 Specdb::NmrOneD 306381 Specdb::NmrOneD 306382 Specdb::NmrOneD 306383 Specdb::NmrOneD 306384 Specdb::NmrOneD 306385 Specdb::NmrOneD 306386 Specdb::NmrOneD 306387 Specdb::NmrOneD 306388 Specdb::NmrOneD 306389 Specdb::NmrOneD 306390 Specdb::MsMs 27020 Specdb::MsMs 27021 Specdb::MsMs 27022 Specdb::MsMs 33578 Specdb::MsMs 33579 Specdb::MsMs 33580 5460111 4573772 C06377 18232 D-GALACTOSAMINE-6-PHOSPHATE 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 Ferreira, F. M., Mendoza-Hernandez, G., Castaneda-Bueno, M., Aparicio, R., Fischer, H., Calcagno, M. L., Oliva, G. (2006). "Structural analysis of N-acetylglucosamine-6-phosphate deacetylase apoenzyme from Escherichia coli." J Mol Biol 359:308-321. 16630633 Raczynska, J., Olchowy, J., Konariev, P. V., Svergun, D. I., Milewski, S., Rypniewski, W. (2007). "The crystal and solution studies of glucosamine-6-phosphate synthase from Candida albicans." J Mol Biol 372:672-688. 17681543 Putative N-acetylgalactosamine-6-phosphate deacetylase P42906 AGAA_ECOLI agaA http://ecmdb.ca/proteins/P42906.xml N-acetylgalactosamine-specific phosphotransferase enzyme IIB component 1 P42909 PTPB1_ECOLI agaB http://ecmdb.ca/proteins/P42909.xml Putative galactosamine-6-phosphate isomerase P42912 AGAI_ECOLI agaI http://ecmdb.ca/proteins/P42912.xml N-acetylgalactosamine permease IIC component 1 P42910 PTPC1_ECOLI agaC http://ecmdb.ca/proteins/P42910.xml N-acetylgalactosamine permease IID component P42911 PTPD_ECOLI agaD http://ecmdb.ca/proteins/P42911.xml N-acetylgalactosamine permease IIC component 1 P42910 PTPC1_ECOLI agaC http://ecmdb.ca/proteins/P42910.xml N-acetylgalactosamine permease IID component P42911 PTPD_ECOLI agaD http://ecmdb.ca/proteins/P42911.xml D-Galactosamine 6-phosphate + Water <> D-Tagatose 6-phosphate + Ammonia R08365 D-Galactosamine + Protein N(pi)-phospho-L-histidine <> D-Galactosamine 6-phosphate + Protein histidine R08367 N-Acetyl-D-galactosamine 6-phosphate + Water > D-Galactosamine 6-phosphate + Acetic acid D-Galactosamine 6-phosphate + Water > D-Tagatose 6-phosphate + Ammonia