2.0 2012-05-31 09:57:45 -0600 2015-06-03 15:53:12 -0600 ECMDB00122 M2MDB000045 D-Glucose Glucose is a monosaccharide containing six carbon atoms and an aldehyde group and is therefore referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In water solution both forms are in equilibrium and at pH 7 the cyclic one is the predominant. 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. α-glucose (+)-Glucose 6-(Hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol A-D-Glucose a-Glucose Alpha-Glucose Anhydrous dextrose Cerelose Cerelose 2001 Clearsweet 95 Clintose L Corn sugar CPC hydrate CPC hydric acid D(+)-Glucose D-glucose Dextropur Dextrose Dextrosol Glucodin Glucolin Glucose Goldsugar Grape sugar Meritose Roferose ST Staleydex 111 Staleydex 95M Tabfine 097(HS) Vadex α-Glucose C6H12O6 180.1559 180.063388116 (3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol glucose 50-99-7 OC[C@H]1OC(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-GASJEMHNSA-N Solid Cytosol Extra-organism Periplasm logp -2.57 ALOGPS logs 0.64 ALOGPS solubility 7.82e+02 g/l ALOGPS melting_point 146-150 oC logp -2.9 ChemAxon pka_strongest_acidic 11.3 ChemAxon pka_strongest_basic -3 ChemAxon iupac (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]1OC(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-GASJEMHNSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 35.92 ChemAxon polarizability 16.37 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 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 Amino sugar and nucleotide sugar metabolism ec00520 Streptomycin biosynthesis ec00521 Butirosin and neomycin biosynthesis ec00524 Microbial metabolism in diverse environments ec01120 Phosphotransferase system (PTS) ec02060 ABC transporters ec02010 Two-component system ec02020 Metabolic pathways eco01100 Lac Operon When glucose is absent and lactose is present in the environment, cyclic AMP is present and binds to the catabolite activator protein (CAP) which in turn binds to the activator binding site and facilitates transcription. Lactose binds to the repressor and prevents it from binding to the operator site. RNA polymerase can now bind to the promoter and carry out transcription of the lac operon. PW000955 Signaling Lac Operon Inactivation 1 When glucose is present, the concentration of cyclic AMP in the cell is low, hence cyclic AMP does not bind to the catabolite activator protein. This leads to the CAP-CAMP complex does not bind to the activator binding site. Therefore RNA polymerase can't bind efficiently to the promoter and transcription does not occur. PW000957 Signaling Lac Operon Inactivation 2 When neither glucose nor lactose is present in the media cell, the concentration of cyclic AMP is high and the catabolite activator protein is bound to the activator binding site, But even though RNA polymerase can bind to the promoter, it is blocked by the repressor on the operator site. Hence there is no transcription of the lac operon PW000956 Signaling Operon: arabinose inactivation The arabinose catabolic pathway operon, araBAD is regulated by the araC regulator and a pBAD promoter. The pathway repressor is glucose. PW001879 Signaling 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 glycogen degradation I GLYCOCAT-PWY trehalose degradation II (trehalase) PWY0-1182 trehalose degradation VI (periplasmic) PWY0-1466 Specdb::CMs 334 Specdb::CMs 335 Specdb::CMs 336 Specdb::CMs 337 Specdb::CMs 1428 Specdb::CMs 1598 Specdb::CMs 1601 Specdb::CMs 1632 Specdb::CMs 1707 Specdb::CMs 2406 Specdb::CMs 30344 Specdb::CMs 30345 Specdb::CMs 30766 Specdb::CMs 30767 Specdb::CMs 31005 Specdb::CMs 31006 Specdb::CMs 31007 Specdb::CMs 31008 Specdb::CMs 31009 Specdb::CMs 37304 Specdb::NmrOneD 1093 Specdb::NmrOneD 1152 Specdb::MsMs 177 Specdb::MsMs 178 Specdb::MsMs 179 Specdb::MsMs 2913 Specdb::MsMs 2914 Specdb::MsMs 2915 Specdb::MsMs 2916 Specdb::MsMs 2917 Specdb::MsMs 178080 Specdb::MsMs 178081 Specdb::MsMs 178082 Specdb::MsMs 180393 Specdb::MsMs 180394 Specdb::MsMs 180395 Specdb::MsMs 437657 Specdb::MsMs 437658 Specdb::MsMs 437659 Specdb::MsMs 437660 Specdb::MsMs 437661 Specdb::MsMs 3609526 Specdb::MsMs 3609527 Specdb::MsMs 3609528 Specdb::MsMs 3610429 Specdb::MsMs 3610430 Specdb::MsMs 3610431 Specdb::NmrTwoD 1151 HMDB00122 5793 5589 C00031 17634 ALPHA-GLUCOSE Dextrose Keseler, I. 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Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 4 pp Beta-galactosidase P00722 BGAL_ECOLI lacZ http://ecmdb.ca/proteins/P00722.xml Xylose isomerase P00944 XYLA_ECOLI xylA http://ecmdb.ca/proteins/P00944.xml Alpha-galactosidase P06720 AGAL_ECOLI melA http://ecmdb.ca/proteins/P06720.xml Evolved beta-galactosidase subunit alpha P06864 BGA2_ECOLI ebgA http://ecmdb.ca/proteins/P06864.xml Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Glucokinase P0A6V8 GLK_ECOLI glk http://ecmdb.ca/proteins/P0A6V8.xml Galactose/methyl galactoside import ATP-binding protein MglA P0AAG8 MGLA_ECOLI mglA http://ecmdb.ca/proteins/P0AAG8.xml 6-phospho-beta-glucosidase BglB P11988 BGLB_ECOLI bglB http://ecmdb.ca/proteins/P11988.xml Periplasmic trehalase P13482 TREA_ECOLI treA http://ecmdb.ca/proteins/P13482.xml Quinoprotein glucose dehydrogenase P15877 DHG_ECOLI gcd http://ecmdb.ca/proteins/P15877.xml 4-alpha-glucanotransferase P15977 MALQ_ECOLI malQ http://ecmdb.ca/proteins/P15977.xml 6-phospho-beta-glucosidase P17411 CHBF_ECOLI chbF http://ecmdb.ca/proteins/P17411.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 6-phospho-beta-glucosidase AscB P24240 ASCB_ECOLI ascB http://ecmdb.ca/proteins/P24240.xml Trehalose-6-phosphate hydrolase P28904 TREC_ECOLI treC http://ecmdb.ca/proteins/P28904.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 PTS system mannose-specific EIIAB component P69797 PTNAB_ECOLI manX http://ecmdb.ca/proteins/P69797.xml Sugar phosphatase supH P75792 SUPH_ECOLI supH http://ecmdb.ca/proteins/P75792.xml Maltose O-acetyltransferase P77791 MAA_ECOLI maa http://ecmdb.ca/proteins/P77791.xml 6-phospho-beta-glucosidase BglA Q46829 BGLA_ECOLI bglA http://ecmdb.ca/proteins/Q46829.xml Galactoside transport system permease protein mglC P23200 MGLC_ECOLI mglC http://ecmdb.ca/proteins/P23200.xml Mannose permease IIC component P69801 PTNC_ECOLI manY http://ecmdb.ca/proteins/P69801.xml Mannose permease IID component P69805 PTND_ECOLI manZ http://ecmdb.ca/proteins/P69805.xml D-galactose-binding periplasmic protein P0AEE5 DGAL_ECOLI mglB http://ecmdb.ca/proteins/P0AEE5.xml Soluble aldose sugar dehydrogenase yliI P75804 YLII_ECOLI yliI http://ecmdb.ca/proteins/P75804.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml Beta-galactosidase G0ZKW2 G0ZKW2_ECOLI lacZ http://ecmdb.ca/proteins/G0ZKW2.xml Galactose/methyl galactoside import ATP-binding protein MglA P0AAG8 MGLA_ECOLI mglA http://ecmdb.ca/proteins/P0AAG8.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 Galactose-proton symporter P0AEP1 GALP_ECOLI galP http://ecmdb.ca/proteins/P0AEP1.xml Sugar efflux transporter A P31675 SETA_ECOLI setA http://ecmdb.ca/proteins/P31675.xml Galactoside transport system permease protein mglC P23200 MGLC_ECOLI mglC http://ecmdb.ca/proteins/P23200.xml Mannose permease IIC component P69801 PTNC_ECOLI manY http://ecmdb.ca/proteins/P69801.xml Mannose permease IID component P69805 PTND_ECOLI manZ http://ecmdb.ca/proteins/P69805.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 Maltoporin P02943 LAMB_ECOLI lamB http://ecmdb.ca/proteins/P02943.xml D-galactose-binding periplasmic protein P0AEE5 DGAL_ECOLI mglB http://ecmdb.ca/proteins/P0AEE5.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 Phosphoenolpyruvic acid + D-Glucose > Glucose 6-phosphate + Pyruvic acid Ubiquinone-8 + D-Glucose + Water > Ubiquinol-8 + Gluconic acid + Hydrogen ion Adenosine triphosphate + Water + D-Glucose > ADP + D-Glucose + Hydrogen ion + Phosphate Adenosine triphosphate + Water + D-Glucose > ADP + D-Glucose + Hydrogen ion + Phosphate Water + alpha-Lactose > D-Galactose + D-Glucose Water + Maltotriose > D-Glucose + D-Maltose RXN0-5183 Water + Maltotetraose > D-Glucose + Maltotriose Water + Maltoheptaose > D-Glucose + Maltohexaose Water + Maltohexaose > D-Glucose + Maltopentaose Water + Maltopentaose > D-Glucose + Maltotetraose Acetyl-CoA + D-Glucose <> 6-Acetyl-D-glucose + Coenzyme A Glucose 6-phosphate + Water > D-Glucose + Phosphate Glucose 1-phosphate + Water > D-Glucose + Phosphate Water + Trehalose >2 D-Glucose Adenosine triphosphate + D-Glucose > ADP + Glucose 6-phosphate + Hydrogen ion D-Maltose + Maltotriose > D-Glucose + Maltotetraose D-Maltose + Maltotetraose > D-Glucose + Maltopentaose D-Maltose + Maltohexaose > D-Glucose + Maltoheptaose D-Maltose + Maltopentaose > D-Glucose + Maltohexaose D-Glucose <> D-Fructose Water + Melibiose > D-Galactose + D-Glucose R01101 Water + Trehalose 6-phosphate > Glucose 6-phosphate + D-Glucose Trehalose + Water <>2 D-Glucose R00010 Adenosine triphosphate + D-Glucose <> ADP + D-Hexose 6-phosphate + Glucose 6-phosphate R00299 Sucrose + Water <> D-Fructose + D-Glucose R00801 Water + Trehalose 6-phosphate <> D-Glucose + D-Hexose 6-phosphate R06113 Melibiose + Water <> D-Galactose + D-Glucose R01101 Protein N(pi)-phospho-L-histidine + D-Glucose <> Protein histidine + Glucose 6-phosphate R02738 Cyanoglycoside + Water <> Cyanohydrin + D-Glucose R04949 cis-beta-D-Glucosyl-2-hydroxycinnamate + Water <> cis-2-Hydroxycinnamate + D-Glucose R04998 1,4-alpha-D-glucan + D-Glucose <> D-Maltose R05196 Neohancoside D + Water <> D-Fructose + D-Glucose R06087 Melibiose + Water <> D-Galactose + D-Glucose R01101 Water + Trehalose 6-phosphate <> D-Glucose + D-Hexose 6-phosphate R06113 Lactose + Water <> D-Glucose + D-Galactose R06114 D-Glucose + Ubiquinone-1 <> Gluconolactone + Ubiquinol-8 R06620 D-Glucose <> b-D-Glucose ALDOSE-1-EPIMERASE-RXN a 1,4-α-D-glucan + Water > a 1,4-α-D-glucan + D-Glucose MALTODEXGLUCOSID-RXN Maltotriose + Water > D-Maltose + D-Glucose RXN0-5183 nigerose + Water D-Glucose RXN0-5395 Trehalose + Water > b-D-Glucose + D-Glucose TREHALA-RXN Alpha-D-glucose 1-phosphate + Water > D-Glucose + Inorganic phosphate 6-Phospho-beta-D-glucosyl-(1,4)-D-glucose + Water > D-Glucose + Glucose 6-phosphate D-Glucose + Ubiquinone-10 > Gluconolactone + Ubiquinol-1 Adenosine triphosphate + D-Glucose > ADP + Glucose 6-phosphate Cellobiose-6-phosphate + Water <> D-Glucose + Glucose 6-phosphate R00839 R06112 Glucose 1-phosphate + Water <> D-Glucose + Phosphate R00304 Trehalose 6-phosphate + Water <> D-Glucose + Glucose 6-phosphate R00837 R06113 D-Glucose + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + beta-D-Glucose 6-phosphate + ADP PW_R003525 Sucrose + Water <> D-Fructose + D-Glucose + D-Fructose PW_R003504 D-Glucose + [PTS enzyme I]-Nπ-phospho-L-histidine > β-D-glucose 1-phosphate + [PTS enzyme I]-L-histidine PW_RCT000152 D-Glucose + Ubiquinone-1 <> Gluconolactone + Ubiquinol-8 Water + Trehalose >2 D-Glucose D-Glucose + Ubiquinone-1 <> Gluconolactone + Ubiquinol-8 Trehalose + Water <>2 D-Glucose