2.0 2012-05-31 14:02:34 -0600 2015-09-13 12:56:13 -0600 ECMDB04025 M2MDB000565 beta-D-Galactose Galactose is an optical isomer of glucose. An aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. Galactose is less sweet than glucose and not very water-soluble. Galactose is a monosaccharide constituent, together with glucose, of the disaccharide lactose. Galactose is produced by hydrolysis of lactose by galactosidase. This enzyme is produced by the lac operon in Escherichia coli (E. coli). Galactan is a polymer of the sugar galactose. It is found in hemicellulose and can be converted to galactose by hydrolysis. 6-(Hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol b D-Galactose b-D-Galactopyranose B-D-Galactose B-D-Galactoside b-D-Galactosides b-delta-Galactoside b-delta-Galactosides B-Galactose b-δ-Galactoside b-δ-Galactosides Beta D-Galactose Beta-D-Galactopyranose Beta-D-Galactose Beta-D-Galactoside Beta-D-Galactosides Beta-delta-Galactoside Beta-delta-galactosides Beta-Galactose Cerebrose D-galactose Delta-Galactose Galactopyranose Galactopyranoside Galactose β D-Galactose β-D-Galactopyranose β-D-Galactose β-D-Galactoside β-D-Galactosides β-Galactose β-δ-Galactoside β-δ-Galactosides δ-Galactose C6H12O6 180.1559 180.063388116 (2R,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol β D-galactose 7296-64-2 OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5-,6-/m1/s1 WQZGKKKJIJFFOK-FPRJBGLDSA-N Solid Extra-organism Periplasm logp -2.57 ALOGPS logs 0.64 ALOGPS solubility 7.82e+02 g/l ALOGPS logp -2.9 ChemAxon pka_strongest_acidic 11.3 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol ChemAxon average_mass 180.1559 ChemAxon mono_mass 180.063388116 ChemAxon smiles OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O ChemAxon formula C6H12O6 ChemAxon inchi InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5-,6-/m1/s1 ChemAxon inchikey WQZGKKKJIJFFOK-FPRJBGLDSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 35.92 ChemAxon polarizability 16.33 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 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 galactose degradation/Leloir Pathway The degradation of galactose, also known as Leloir pathway, requires 3 main enzymes once Beta-D-galactose has been converted to galactose through an Aldose-1-epimerase. These are: galactokinase , galactose-1-phosphate uridylyltransferase and UDP-glucose 4-epimerase. Beta-D-galactose can be uptaken from the environment through a galactose proton symporter. It 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. 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. PW000884 Metabolic inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 Metabolic galactose degradation I (Leloir pathway) GALACTMETAB-PWY lactose degradation III BGALACT-PWY Specdb::CMs 2500 Specdb::CMs 38603 Specdb::CMs 160259 Specdb::NmrOneD 21902 Specdb::NmrOneD 21903 Specdb::NmrOneD 21904 Specdb::NmrOneD 21905 Specdb::NmrOneD 21906 Specdb::NmrOneD 21907 Specdb::NmrOneD 21908 Specdb::NmrOneD 21909 Specdb::NmrOneD 21910 Specdb::NmrOneD 21911 Specdb::NmrOneD 21912 Specdb::NmrOneD 21913 Specdb::NmrOneD 21914 Specdb::NmrOneD 21915 Specdb::NmrOneD 21916 Specdb::NmrOneD 21917 Specdb::NmrOneD 21918 Specdb::NmrOneD 21919 Specdb::NmrOneD 21920 Specdb::NmrOneD 21921 Specdb::MsMs 2316 Specdb::MsMs 2317 Specdb::MsMs 2318 Specdb::MsMs 182655 Specdb::MsMs 182656 Specdb::MsMs 182657 Specdb::MsMs 183003 Specdb::MsMs 183004 Specdb::MsMs 183005 Specdb::MsMs 1471166 Specdb::MsMs 2423147 Specdb::MsMs 2423148 Specdb::MsMs 2423149 Specdb::MsMs 2513234 Specdb::MsMs 2513235 Specdb::MsMs 2513236 HMDB03449 439353 388476 C00962 GALACTOSE GLB GAL Keseler, I. 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Journal of the American Chemical Society (1957), 79 3868-71. http://hmdb.ca/system/metabolites/msds/000/003/030/original/HMDB03449.pdf?1358461766 Beta-galactosidase P00722 BGAL_ECOLI lacZ http://ecmdb.ca/proteins/P00722.xml Aldose 1-epimerase P0A9C3 GALM_ECOLI galM http://ecmdb.ca/proteins/P0A9C3.xml ABC transporter periplasmic-binding protein ytfQ P39325 YTFQ_ECOLI ytfQ http://ecmdb.ca/proteins/P39325.xml Galactoside transport system permease protein mglC P23200 MGLC_ECOLI mglC http://ecmdb.ca/proteins/P23200.xml Melibiose carrier protein P02921 MELB_ECOLI melB http://ecmdb.ca/proteins/P02921.xml Sugar efflux transporter A P31675 SETA_ECOLI setA http://ecmdb.ca/proteins/P31675.xml Sugar efflux transporter C P31436 SETC_ECOLI setC http://ecmdb.ca/proteins/P31436.xml ABC transporter periplasmic-binding protein ytfQ P39325 YTFQ_ECOLI ytfQ http://ecmdb.ca/proteins/P39325.xml Galactoside transport system permease protein mglC P23200 MGLC_ECOLI mglC http://ecmdb.ca/proteins/P23200.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 beta-D-Galactose > D-Galactose Alpha-D-Galactose > beta-D-Galactose PW_R002953 beta-D-Galactose > Alpha-D-Galactose PW_R002954 alpha-Lactose + Water > beta-D-Galactose + Beta-D-Glucose + b-D-Glucose PW_R002956