2.0 2012-05-31 14:29:43 -0600 2015-06-03 17:19:24 -0600 ECMDB20142 M2MDB000990 D-Galactosamine D-galactosamine is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. D-Galactosamine is an amino sugar with unique hepatotoxic properties in animals. (PMID 6338507) 2-Amino-2-deoxy-D-galactopyranose 2-Amino-2-deoxy-D-galactose Chondrosamine D-2-Amino-2-deoxygalactose D-Chondrosamine D-galactosamine Galactosamine C6H13NO5 179.1711 179.079372531 (3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol galactosamine 7535-00-4 N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1 MSWZFWKMSRAUBD-GASJEMHNSA-N Cytoplasm Periplasm logp -2.73 ALOGPS logs 0.49 ALOGPS solubility 5.51e+02 g/l ALOGPS logp -3 ChemAxon pka_strongest_acidic 11.73 ChemAxon pka_strongest_basic 8.23 ChemAxon iupac (3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol ChemAxon average_mass 179.1711 ChemAxon mono_mass 179.079372531 ChemAxon smiles N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O ChemAxon formula C6H13NO5 ChemAxon inchi InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1 ChemAxon inchikey MSWZFWKMSRAUBD-GASJEMHNSA-N ChemAxon polar_surface_area 116.17 ChemAxon refractivity 37.58 ChemAxon polarizability 16.72 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 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 1085168 Specdb::NmrOneD 265348 Specdb::NmrOneD 265349 Specdb::NmrOneD 265350 Specdb::NmrOneD 265351 Specdb::NmrOneD 265352 Specdb::NmrOneD 265353 Specdb::NmrOneD 265354 Specdb::NmrOneD 265355 Specdb::NmrOneD 265356 Specdb::NmrOneD 265357 Specdb::NmrOneD 265358 Specdb::NmrOneD 265359 Specdb::NmrOneD 265360 Specdb::NmrOneD 265361 Specdb::NmrOneD 265362 Specdb::NmrOneD 265363 Specdb::NmrOneD 265364 Specdb::NmrOneD 265365 Specdb::NmrOneD 265366 Specdb::NmrOneD 265367 Specdb::MsMs 23993 Specdb::MsMs 23994 Specdb::MsMs 23995 Specdb::MsMs 30791 Specdb::MsMs 30792 Specdb::MsMs 30793 24154 22576 C02262 28328 GALACTOSAMINE 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 Camara, D. S., Caruana, J. A. Jr, Schwartz, K. A., Montes, M., Nolan, J. P. (1983). "D-Galactosamine liver injury: absorption of endotoxin and protective effect of small bowel and colon resection in rabbits." Proc Soc Exp Biol Med 172:255-259. 6338507 N-acetylgalactosamine-specific phosphotransferase enzyme IIB component 1 P42909 PTPB1_ECOLI agaB http://ecmdb.ca/proteins/P42909.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 + Protein N(pi)-phospho-L-histidine <> D-Galactosamine 6-phosphate + Protein histidine R08367