2.0 2012-10-10 12:14:37 -0600 2015-08-05 16:22:04 -0600 ECMDB23064 M2MDB003454 Alpha-D-glucose 6-phosphate A D-glucopyranose 6-phosphate where α-D-glucose is the sugar component 6-O-phosphono-a-D-Glucopyranose 6-O-phosphono-alpha-D-Glucopyranose 6-O-phosphono-α-D-glucopyranose a-D-Glucose 6-phosphate a-D-Glucose 6-phosphoric acid a-D-GLUCOSE-6-phosphate a-D-GLUCOSE-6-phosphoric acid alpha-D-Glucose 6-phosphoric acid ALPHA-D-GLUCOSE-6-phosphATE alpha-D-GLUCOSE-6-phosphoric acid α-D-glucose 6-phosphate α-D-Glucose 6-phosphate α-D-glucose 6-phosphoric acid α-D-Glucose 6-phosphoric acid α-D-glucose-6-phosphate α-D-glucose-6-phosphoric acid C6H13O9P 260.1358 260.029718526 {[(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid α-D-glucose 6-phosphate O[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6+/m1/s1 NBSCHQHZLSJFNQ-DVKNGEFBSA-N logp -2.06 ALOGPS logs -0.92 ALOGPS solubility 3.14e+01 g/l ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac {[(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 260.1358 ChemAxon mono_mass 260.029718526 ChemAxon smiles O[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O ChemAxon formula C6H13O9P ChemAxon inchi InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6+/m1/s1 ChemAxon inchikey NBSCHQHZLSJFNQ-DVKNGEFBSA-N ChemAxon polar_surface_area 156.91 ChemAxon refractivity 46.8 ChemAxon polarizability 20.56 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Starch and sucrose metabolism The metabolism of starch and sucrose begins with D-fructose interacting with a D-glucose in a reversible reaction through a maltodextrin glucosidase resulting in a water molecule and a sucrose. D-fructose is phosphorylated through an ATP driven fructokinase resulting in the release of an ADP, a hydrogen ion and a Beta-D-fructofuranose 6-phosphate. This compound can also be introduced into the cytoplasm through either a mannose PTS permease or a hexose-6-phosphate:phosphate antiporter. The Beta-D-fructofuranose 6-phosphate is isomerized through a phosphoglucose isomerase resulting in a Beta-D-glucose 6-phosphate. This compound can also be incorporated by glucose PTS permease or a hexose-6-phosphate:phosphate antiporter. The beta-D-glucose 6 phosphate can also be produced by a D-glucose being phosphorylated by an ATP-driven glucokinase resulting in a ADP, a hydrogen ion and a Beta-D-glucose 6 phosphate. The beta-D-glucose can produce alpha-D-glucose-1-phosphate by two methods: 1.-Beta-D-glucose is isomerized into an alpha-D-Glucose 6-phosphate and then interacts in a reversible reaction through a phosphoglucomutase-1 resulting in a alpha-D-glucose-1-phosphate. 2.-Beta-D-glucose interacts with a putative beta-phosphoglucomutase resulting in a Beta-D-glucose 1-phosphate. Beta-D-glucose 1-phosphate can be incorporated into the cytoplasm through a glucose PTS permease. This compound is then isomerized into a Alpha-D-glucose-1-phosphate The beta-D-glucose can cycle back into a D-fructose by first interacting with D-fructose in a reversible reaction through a Polypeptide: predicted glucosyltransferase resulting in the release of a phosphate and a sucrose. The sucrose then interacts in a reversible reaction with a water molecule through a maltodextrin glucosidase resulting in a D-glucose and a D-fructose. Alpha-D-glucose-1-phosphate can produce glycogen in by two different sets of reactions: 1.-Alpha-D-glucose-1-phosphate interacts with a hydrogen ion and an ATP through a glucose-1-phosphate adenylyltransferase resulting in a pyrophosphate and an ADP-glucose. The ADP-glucose then interacts with an amylose through a glycogen synthase resulting in the release of an ADP and an Amylose. The amylose then interacts with 1,4-α-glucan branching enzyme resulting in glycogen 2.- Alpha-D-glucose-1-phosphate interacts with amylose through a maltodextrin phosphorylase resulting in a phosphate and a glycogen. Alpha-D-glucose-1-phosphate can also interacts with UDP-galactose through a galactose-1-phosphate uridylyltransferase resulting in a galactose 1-phosphate and a Uridine diphosphate glucose. The UDP-glucose then interacts with an alpha-D-glucose 6-phosphate through a trehalose-6-phosphate synthase resulting in a uridine 5'-diphosphate, a hydrogen ion and a Trehalose 6- phosphate. The latter compound can also be incorporated into the cytoplasm through a trehalose PTS permease. Trehalose interacts with a water molecule through a trehalose-6-phosphate phosphatase resulting in the release of a phosphate and an alpha,alpha-trehalose.The alpha,alpha-trehalose can also be obtained from glycogen being metabolized through a glycogen debranching enzyme resulting in a the alpha, alpha-trehalose. This compound ca then be hydrated through a cytoplasmic trehalase resulting in the release of an alpha-D-glucose and a beta-d-glucose. Glycogen is then metabolized by reacting with a phosphate through a glycogen phosphorylase resulting in a alpha-D-glucose-1-phosphate and a dextrin. The dextrin is then hydrated through a glycogen phosphorylase-limit dextrin α-1,6-glucohydrolase resulting in the release of a debranched limit dextrin and a maltotetraose. This compound can also be incorporated into the cytoplasm through a maltose ABC transporter. The maltotetraose interacts with a phosphate through a maltodextrin phosphorylase releasing a alpha-D-glucose-1-phosphate and a maltotriose. The maltotriose can also be incorporated through a maltose ABC transporter. The maltotriose can then interact with water through a maltodextrin glucosidase resulting in a D-glucose and a D-maltose. D-maltose can also be incorporated through a maltose ABC transporter The D-maltose can then interact with a maltotriose through a amylomaltase resulting in a maltotetraose and a D-glucose. The D-glucose is then phosphorylated through an ATP driven glucokinase resulting in a hydrogen ion, an ADP and a Beta-D-glucose 6-phosphate PW000941 ec00500 Metabolic Glycolysis / Gluconeogenesis ec00010 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 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 colanic acid building blocks biosynthesis The colonic acid building blocks biosynthesis starts with a Beta-D-Glucose undergoing a transport reaction mediated by a glucose PTS permease. The permease phosphorylates the Beta-D-Glucose, producing a Beta-D-Glucose 6-phosphate. This compound can either change to an Alpha-D-Glucose 6-phosphate spontaneously or into a fructose 6-phosphate through a glucose-6-phosphate isomerase. The latter compound can also be present in E.coli through the interaction of D-fructose and a mannose PTS permease which phosphorylate the D-fructose. Fructose 6-phosphate interacts in a reversible reaction with mannose-6-phosphate isomerase in order to produce a Alpha-D-mannose 6-phosphate. This compound can also be present in E.coli through the interaction of Alpha-D-mannose and a mannose PTS permease which phosphorylates the alpha-D-mannose. Alpha-D-mannose 6-phosphate interacts in a reversible reaction with a phosphomannomutase to produce a alpha-D-mannose 1-phosphate. This compound in turn with a hydrogen ion and gtp undergoes a reaction with a mannose-1-phosphate guanylyltransferase, releasing a pyrophosphate and producing a guanosine diphosphate mannose. Guanosine diphosphate mannose interacts with gdp-mannose 4,6-dehydratase releasing a water, and gdp-4-dehydro-6-deoxy-D-mannose. This compound in turn with hydrogen ion and NADPH interact with GDP-L-fucose synthase releasing NADP and producing a GDP-L-fucose. The Alpha-D-Glucose 6-phosphate interacts in a reversible reaction with phosphoglucomutase-1 to produce a alpha-D-glucose 1-phosphate. This in turn with UTP and hydrogen ion interact with UTP--glucose-1-phosphate uridyleltransferase releasing a pyrophosphate and UDP-glucose. UDP-glucose can either interact with galactose-1-phosphate uridylyltransferase to produce a UDP-galactose or in turn with NAD and water interact with UDP-glucose 6-dehydrogenase releasing a NADH and a hydrogen ion and producing a UDP-glucuronate. GDP-L-fucose, UDP-glucose, UDP-galactose and UDP-glucuronate are sugars that need to be activated in the form of nucleotide sugar prior to their assembly into colanic acid, also known as M antigen. Colanic acid is an extracellular polysaccharide which has been linked to a cluster of 19 genes(wca). PW000951 Metabolic Specdb::CMs 3404 Specdb::NmrOneD 304771 Specdb::NmrOneD 304772 Specdb::NmrOneD 304773 Specdb::NmrOneD 304774 Specdb::NmrOneD 304775 Specdb::NmrOneD 304776 Specdb::NmrOneD 304777 Specdb::NmrOneD 304778 Specdb::NmrOneD 304779 Specdb::NmrOneD 304780 Specdb::NmrOneD 304781 Specdb::NmrOneD 304782 Specdb::NmrOneD 304783 Specdb::NmrOneD 304784 Specdb::NmrOneD 304785 Specdb::NmrOneD 304786 Specdb::NmrOneD 304787 Specdb::NmrOneD 304788 Specdb::NmrOneD 304789 Specdb::NmrOneD 304790 Specdb::MsMs 26615 Specdb::MsMs 26616 Specdb::MsMs 26617 Specdb::MsMs 33173 Specdb::MsMs 33174 Specdb::MsMs 33175 Specdb::MsMs 438863 Specdb::MsMs 438864 Specdb::MsMs 438865 Specdb::MsMs 447727 Specdb::MsMs 447728 Specdb::MsMs 447729 C00668 G6P Glucose-6-phosphate isomerase P0A6T1 G6PI_ECOLI pgi http://ecmdb.ca/proteins/P0A6T1.xml Glucokinase P0A6V8 GLK_ECOLI glk http://ecmdb.ca/proteins/P0A6V8.xml Alpha,alpha-trehalose-phosphate synthase [UDP-forming] P31677 OTSA_ECOLI otsA http://ecmdb.ca/proteins/P31677.xml Phosphoglucomutase P36938 PGM_ECOLI pgm http://ecmdb.ca/proteins/P36938.xml Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml PTS system glucose-specific EIICB component P69786 PTGCB_ECOLI ptsG http://ecmdb.ca/proteins/P69786.xml conserved protein P39173 yeaD http://ecmdb.ca/proteins/P39173.xml PTS system glucose-specific EIICB component P69786 PTGCB_ECOLI ptsG http://ecmdb.ca/proteins/P69786.xml Alpha-D-glucose 1-phosphate > Alpha-D-glucose 6-phosphate Alpha-D-glucose 6-phosphate > beta-D-Glucose 6-phosphate Glucose 6-phosphate + Alpha-D-glucose 6-phosphate <> beta-D-Glucose 6-phosphate R02739 Alpha-D-glucose 6-phosphate > α-D-glucose 1-phosphate PW_R002947 Alpha-D-glucose 6-phosphate <> Alpha-D-glucose 1-phosphate PW_R003510 UDP-Glucose + Alpha-D-glucose 6-phosphate > Uridine 5'-diphosphate + Trehalose 6-phosphate + Hydrogen ion + Uridine 5'-diphosphate PW_R003513 Glucose 6-phosphate + Alpha-D-glucose 6-phosphate <> beta-D-Glucose 6-phosphate Glucose 6-phosphate + Alpha-D-glucose 6-phosphate <> beta-D-Glucose 6-phosphate