2.0 2012-05-31 14:02:06 -0600 2015-10-02 02:25:51 -0600 ECMDB04012 M2MDB000557 Alpha-D-Galactose D-galactose metabolism can be an important factor in virulence in different bacteria. In Escherichia coli, galactose is utilized by the Leloir pathway (galactose degradation I). Alpha-D-Galactose is a substrate of enzyme galactokinase, the first enzyme of the Leloir pathway [PMID: 21712421], which catalyzes the chemical reaction alpha-D-galactose + ATP -> alpha-D-galactose 1-phosphate + ADP + H+ (EcoCyc compound: ALPHA-D-GALACTOSE). (+)-Galactose 5abp 6-(Hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol 8abp a D-Galactose a-D-Galactopyranose a-D-Galactose Alpha D-Galactose Alpha-D-Galactopyranose Alpha-D-Galactose Cerebrose D-(+)-Galactose D-Galactose GAL Galactopyranose Galactopyranoside Galactose Galactose (NF) GLA GLC Hexose α D-Galactose α-D-Galactopyranose α-D-Galactose C6H12O6 180.1559 180.063388116 (2S,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol galactose 59-23-4 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-PHYPRBDBSA-N Solid Cytoplasm Periplasm logp -2.57 ALOGPS logs 0.64 ALOGPS solubility 7.82e+02 g/l ALOGPS melting_point 170 oC logp -2.9 ChemAxon pka_strongest_acidic 11.3 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S,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-PHYPRBDBSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 35.92 ChemAxon polarizability 16.13 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 Amino sugar and nucleotide sugar metabolism ec00520 Bacterial chemotaxis ec02030 Metabolic pathways eco01100 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 galactose degradation I (Leloir pathway) GALACTMETAB-PWY lactose degradation III BGALACT-PWY Specdb::CMs 2738 Specdb::CMs 37318 Specdb::CMs 102609 Specdb::CMs 102610 Specdb::CMs 102611 Specdb::CMs 102612 Specdb::CMs 102613 Specdb::CMs 102614 Specdb::CMs 102615 Specdb::CMs 102616 Specdb::CMs 102617 Specdb::CMs 102618 Specdb::CMs 102619 Specdb::CMs 102620 Specdb::CMs 102621 Specdb::CMs 102622 Specdb::CMs 102623 Specdb::CMs 102624 Specdb::CMs 102625 Specdb::CMs 102626 Specdb::CMs 135841 Specdb::CMs 143575 Specdb::CMs 1051447 Specdb::CMs 1051449 Specdb::CMs 1051451 Specdb::NmrOneD 1108 Specdb::NmrOneD 1166 Specdb::NmrOneD 4756 Specdb::NmrOneD 142530 Specdb::NmrOneD 142531 Specdb::NmrOneD 142532 Specdb::NmrOneD 142533 Specdb::NmrOneD 142534 Specdb::NmrOneD 142535 Specdb::NmrOneD 142536 Specdb::NmrOneD 142537 Specdb::NmrOneD 142538 Specdb::NmrOneD 142539 Specdb::NmrOneD 142540 Specdb::NmrOneD 142541 Specdb::NmrOneD 142542 Specdb::NmrOneD 142543 Specdb::NmrOneD 142544 Specdb::NmrOneD 142545 Specdb::NmrOneD 142546 Specdb::NmrOneD 142547 Specdb::NmrOneD 142548 Specdb::NmrOneD 142549 Specdb::NmrOneD 166521 Specdb::MsMs 215 Specdb::MsMs 216 Specdb::MsMs 217 Specdb::MsMs 178761 Specdb::MsMs 178762 Specdb::MsMs 178763 Specdb::MsMs 181080 Specdb::MsMs 181081 Specdb::MsMs 181082 Specdb::MsMs 1471230 Specdb::MsMs 1471231 Specdb::MsMs 1471232 Specdb::MsMs 2231542 Specdb::MsMs 2232625 Specdb::MsMs 2235043 Specdb::MsMs 2677854 Specdb::MsMs 2677855 Specdb::MsMs 2677856 Specdb::MsMs 3030857 Specdb::MsMs 3030858 Specdb::MsMs 3030859 Specdb::NmrTwoD 968 Specdb::NmrTwoD 1166 HMDB00143 439357 388480 C00984 28061 GALACTOSE GLA Alpha-D-galactose Keseler, I. 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Alpha-galactosidase P06720 AGAL_ECOLI melA http://ecmdb.ca/proteins/P06720.xml Galactokinase P0A6T3 GAL1_ECOLI galK http://ecmdb.ca/proteins/P0A6T3.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 Galactose-proton symporter P0AEP1 GALP_ECOLI galP http://ecmdb.ca/proteins/P0AEP1.xml ABC transporter periplasmic-binding protein ytfQ P39325 YTFQ_ECOLI ytfQ http://ecmdb.ca/proteins/P39325.xml Adenosine triphosphate + D-Galactose + Alpha-D-Galactose <> ADP + Galactose 1-phosphate + Hydrogen ion R01092 GALACTOKIN-RXN Alpha-D-Galactose + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + Galactose 1-phosphate + ADP + Galactose 1-phosphate PW_R002952 Alpha-D-Galactose > beta-D-Galactose PW_R002953 beta-D-Galactose > Alpha-D-Galactose PW_R002954 Melibiose + Water > Alpha-D-Galactose + Beta-D-Glucose + b-D-Glucose PW_R003298