2.0 2012-05-31 13:58:38 -0600 2015-09-13 12:56:12 -0600 ECMDB03345 M2MDB000492 alpha-D-Glucose Alpha-D-Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. Alpha-D-Glucose is an intermediate in glycolysis/gluconeogenesis pathway where it is converted to beta-D-glucose via galactose-1-epimerase (mutarotase) (EC:5.1.3.3). It is also involved in several other metabolic pathways: fructose and mannose metabolism, galactose metabolism, starch and sucrose metabolism and amino sugar and nucleotide sugar metabolism. &alpha;-glucose 6-(Hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol A-D-Glucopyranose A-D-Glucose a-delta-Glucopyranose a-delta-Glucose A-Dextrose A-Glucose a-δ-Glucopyranose a-δ-Glucose Alpha-D-Glucopyranose Alpha-D-Glucose Alpha-delta-Glucopyranose Alpha-delta-Glucose Alpha-Dextrose Alpha-Glucose D-glucose Glucose Hexopyranose α-D-Glucopyranose α-D-Glucose α-Dextrose α-Glucose α-δ-Glucopyranose α-δ-Glucose C6H12O6 180.1559 180.063388116 (2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol α-glucose 492-62-6 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-DVKNGEFBSA-N Solid Cytoplasm Periplasm logp -2.57 ALOGPS logs 0.64 ALOGPS solubility 7.82e+02 g/l ALOGPS melting_point 146 oC logp -2.9 ChemAxon pka_strongest_acidic 11.3 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S,3R,4S,5S,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-DVKNGEFBSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 35.92 ChemAxon polarizability 16.09 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 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 Fructose and mannose metabolism ec00051 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 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Amino sugar and nucleotide sugar metabolism II The synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate. N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound is then deaminased into Beta-D-fructofuranose 6-phosphate through a glucosamine-6-phosphate deaminase. The beta-D-fructofuranose 6 -phosphate is isomerized in a reversible reaction into an alpha-D-mannose 6-phosphate. This compound can also be introduced into the cell from the periplasmic space through a mannose PTS permease that phosphorylates an alpha-D-mannose. Alpha-D-mannose 6-phosphate undergoes a reversible reaction through a phosphomannomutase to produce an alpha-D-mannose 1-phosphate. The alpha-D-mannose 1-phosphate enters the nucleotide sugar metabolism through a reaction with GTP producing a GDP-mannose and releasing a pyrophosphate, all through a mannose-1-phosphate guanylyltransferase. GDP-mannose is then dehydrated to produce GDP-4-dehydro-6-deoxy-alpha-D-mannose through a GDP-mannose 4,6-dehydratase. This compound is then used to synthesize GDP-Beta-L-fucose through a NADPH dependent GDP-L-fucose synthase. Alpha-D-glucose is introduced into the cytoplasm through a glucose PTS permease, which phosphorylates the compound in order to produce an alpha-D-glucose 6-phosphate. This compound is then modified through a phosphoglucomutase 1 to yield alpha-D-glucose 1-phosphate. This compound can either be adenylated to produce ADP-glucose or uridylylated to produce galactose 1-phosphate through glucose-1-phosphate adenyllyltransferase and galactose-1-phosphate uridylyltransferase respectively. PW000887 Metabolic Amino sugar and nucleotide sugar metabolism III The synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate. N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound is then deaminased into Beta-D-fructofuranose 6-phosphate through a glucosamine-6-phosphate deaminase. Beta-D-fructofuranose 6-phosphate is isomerized into a beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase. The compound is then isomerized by a putative beta-phosphoglucomutase to produce a beta-D-glucose 1-phosphate. This compound enters the nucleotide sugar metabolism through uridylation resulting in a UDP-glucose. UDP-glucose is then dehydrated through a UDP-glucose 6-dehydrogenase to produce a UDP-glucuronic acid. This compound undergoes a NAD dependent reaction through a bifunctional polymyxin resistance protein to produce UDP-Beta-L-threo-pentapyranos-4-ulose. This compound then reacts with L-glutamic acid through a UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase to produce an oxoglutaric acid and UDP-4-amino-4-deoxy-beta-L-arabinopyranose The latter compound interacts with a N10-formyl-tetrahydrofolate through a bifunctional polymyxin resistance protein ArnA, resulting in a tetrahydrofolate, a hydrogen ion and a UDP-4-deoxy-4-formamido-beta-L-arabinopyranose, which in turn reacts with a product of the methylerythritol phosphate and polysoprenoid biosynthesis pathway, di-trans,octa-cis-undecaprenyl phosphate to produce a 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate. Alpha-D-glucose is introduced into the cytoplasm through a glucose PTS permease, which phosphorylates the compound in order to produce an alpha-D-glucose 6-phosphate. This compound is then modified through a phosphoglucomutase 1 to yield alpha-D-glucose 1-phosphate. This compound can either be adenylated to produce ADP-glucose or uridylylated to produce galactose 1-phosphate through glucose-1-phosphate adenyllyltransferase and galactose-1-phosphate uridylyltransferase respectively. PW000895 Metabolic Secondary metabolites: Trehalose Biosynthesis and Metabolism Threhalose biosynthesis begins with an Alpha-D-glucose-1-phosphate interacting with an ATP through a glucose-1-phosphate adenylyltransferase resulting in the release of a pyrophosphate and an ADP-glucose. The latter compound interacts in a reversible reaction with an amylose through a glycogen synthase resulting in the release of an ADP and an amylose. Amylose then interacts in a reversible reaction with 1,4-α-glucan branching enzyme resulting in a glycogen Glycogen can also be produced by a reversible reaction with Amylose through a maltodextrin phosphorylase, releasing a phosphate and a glycogen. Glycogen is then transformed into trehalose through a glycogen debranching enzyme. Trehalose then interacts with a water molecule through a cytoplasmic trehalase resulting in the release of a Beta-D-glucose and an Alpha-D-glucose. The beta-D-glucose is then phosphorylated by and ATP driven glucokinase resulting in a hydrogen ion, an ADP and a Beta-D-glucose 6-phosphate. PW000968 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 glycogen degradation I GLYCOCAT-PWY trehalose degradation II (trehalase) PWY0-1182 trehalose degradation VI (periplasmic) PWY0-1466 Specdb::CMs 2676 Specdb::CMs 38578 Specdb::CMs 161153 Specdb::NmrOneD 1953 Specdb::NmrOneD 4817 Specdb::NmrOneD 135690 Specdb::NmrOneD 135691 Specdb::NmrOneD 135692 Specdb::NmrOneD 135693 Specdb::NmrOneD 135694 Specdb::NmrOneD 135695 Specdb::NmrOneD 135696 Specdb::NmrOneD 135697 Specdb::NmrOneD 135698 Specdb::NmrOneD 135699 Specdb::NmrOneD 135700 Specdb::NmrOneD 135701 Specdb::NmrOneD 135702 Specdb::NmrOneD 135703 Specdb::NmrOneD 135704 Specdb::NmrOneD 135705 Specdb::NmrOneD 135706 Specdb::NmrOneD 135707 Specdb::NmrOneD 135708 Specdb::NmrOneD 135709 Specdb::MsMs 2253028 Specdb::MsMs 2253423 Specdb::MsMs 2255077 Specdb::MsMs 2255515 Specdb::MsMs 2257119 Specdb::MsMs 2257455 Specdb::MsMs 2254 Specdb::MsMs 2255 Specdb::MsMs 180975 Specdb::MsMs 180976 Specdb::MsMs 180977 Specdb::MsMs 3094168 Specdb::MsMs 3094169 Specdb::MsMs 3094170 Specdb::MsMs 178656 Specdb::MsMs 178657 Specdb::MsMs 178658 Specdb::MsMs 3046369 Specdb::MsMs 3046370 Specdb::MsMs 3046371 Specdb::NmrTwoD 1886 HMDB03345 79025 71358 C00267 17925 ALPHA-GLUCOSE GLC Keseler, I. 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Conversion of sucrose to b-D-glucose using three-stage immobilized enzyme process. U.S. (2007), 12pp. http://hmdb.ca/system/metabolites/msds/000/002/926/original/HMDB03345.pdf?1358463389 Beta-galactosidase P00722 BGAL_ECOLI lacZ http://ecmdb.ca/proteins/P00722.xml Xylose isomerase P00944 XYLA_ECOLI xylA http://ecmdb.ca/proteins/P00944.xml Evolved beta-galactosidase subunit alpha P06864 BGA2_ECOLI ebgA http://ecmdb.ca/proteins/P06864.xml Glucokinase P0A6V8 GLK_ECOLI glk http://ecmdb.ca/proteins/P0A6V8.xml Aldose 1-epimerase P0A9C3 GALM_ECOLI galM http://ecmdb.ca/proteins/P0A9C3.xml Periplasmic trehalase P13482 TREA_ECOLI treA http://ecmdb.ca/proteins/P13482.xml PTS system maltose- and glucose-specific EIICB component P19642 PTOCB_ECOLI malX http://ecmdb.ca/proteins/P19642.xml Glucose-1-phosphatase P19926 AGP_ECOLI agp http://ecmdb.ca/proteins/P19926.xml Maltodextrin glucosidase P21517 MALZ_ECOLI malZ http://ecmdb.ca/proteins/P21517.xml Alpha-glucosidase yihQ P32138 YIHQ_ECOLI yihQ http://ecmdb.ca/proteins/P32138.xml Periplasmic beta-glucosidase P33363 BGLX_ECOLI bglX http://ecmdb.ca/proteins/P33363.xml Cytoplasmic trehalase P62601 TREF_ECOLI treF http://ecmdb.ca/proteins/P62601.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 cryptic beta-D-galactosidase, beta subunit P0AC73 ebgC http://ecmdb.ca/proteins/P0AC73.xml Beta-galactosidase G0ZKW2 G0ZKW2_ECOLI lacZ http://ecmdb.ca/proteins/G0ZKW2.xml PTS system maltose- and glucose-specific EIICB component P19642 PTOCB_ECOLI malX http://ecmdb.ca/proteins/P19642.xml PTS system glucose-specific EIICB component P69786 PTGCB_ECOLI ptsG http://ecmdb.ca/proteins/P69786.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 D-Maltose + Water <>2 alpha-D-Glucose R00028 Sucrose + Water <> beta-D-Fructose + alpha-D-Glucose R00802 alpha-D-Glucose <> D-Fructose R00878 Glucose 1-phosphate + Water <> alpha-D-Glucose + Phosphate R00947 alpha-D-Glucose <> b-D-Glucose R01602 alpha-Lactose + Water <> alpha-D-Glucose + D-Galactose R01678 Adenosine triphosphate + alpha-D-Glucose <> ADP + Glucose 6-phosphate R01786 D-Glucoside + Water <> ROH + alpha-D-Glucose R03527 Neohancoside D + Water <> beta-D-Fructose + alpha-D-Glucose R06088 alpha-D-Glucose > b-D-Glucose R01602 Trehalose + Water > b-D-Glucose + alpha-D-Glucose Trehalose + Water <> b-D-Glucose + alpha-D-Glucose R00010 R06103 α,α-trehalose + Water > alpha-D-Glucose + Beta-D-Glucose + b-D-Glucose PW_R003516 alpha-D-Glucose + HPr - phosphorylated > α-D-glucose 6-phosphate + HPr + Mannose 6-phosphate PW_RCT000133