2.0 2012-05-31 14:31:16 -0600 2015-06-03 17:19:27 -0600 ECMDB20171 M2MDB001018 Maltose 6'-phosphate Maltose 6'-phosphate is a member of the chemical class known as Dihexoses. These are disaccharides containing two hexose carbohydrates. (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yloxyoxan-2-ylmethyl dihydrogen phosphate (2R,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yloxyoxan-2-ylmethyl dihydrogen phosphoric acid 4-O-(6-O-phosphono-a-D-Glucopyranosyl)-a-D-glucopyranose 4-O-(6-O-Phosphono-alpha-D-glucopyranosyl)-alpha-D-glucopyranose 4-O-(6-O-phosphono-α-D-Glucopyranosyl)-α-D-glucopyranose Maltose 6'-phosphoric acid C12H23O14P 422.2764 422.082541956 {[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}phosphonic acid maltose 6'-phosphate [H][C@]1(O)O[C@]([H])(CO)[C@@]([H])(O[C@@]2([H])O[C@]([H])(COP(O)(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)[C@@]1([H])O InChI=1S/C12H23O14P/c13-1-3-10(7(16)8(17)11(19)24-3)26-12-9(18)6(15)5(14)4(25-12)2-23-27(20,21)22/h3-19H,1-2H2,(H2,20,21,22)/t3-,4-,5-,6+,7-,8-,9-,10-,11+,12-/m1/s1 ITPHOIFCAFNCLL-ASMJPISFSA-N Cytosol logp -2.42 ALOGPS logs -1.02 ALOGPS solubility 4.07e+01 g/l ALOGPS logp -4.8 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac {[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 422.2764 ChemAxon mono_mass 422.082541956 ChemAxon smiles [H][C@]1(O)O[C@]([H])(CO)[C@@]([H])(O[C@@]2([H])O[C@]([H])(COP(O)(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)[C@@]1([H])O ChemAxon formula C12H23O14P ChemAxon inchi InChI=1S/C12H23O14P/c13-1-3-10(7(16)8(17)11(19)24-3)26-12-9(18)6(15)5(14)4(25-12)2-23-27(20,21)22/h3-19H,1-2H2,(H2,20,21,22)/t3-,4-,5-,6+,7-,8-,9-,10-,11+,12-/m1/s1 ChemAxon inchikey ITPHOIFCAFNCLL-ASMJPISFSA-N ChemAxon polar_surface_area 236.06 ChemAxon refractivity 79.21 ChemAxon polarizability 35.37 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 13 ChemAxon donor_count 9 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 Specdb::CMs 1083710 Specdb::EiMs 4699 Specdb::NmrOneD 330702 Specdb::NmrOneD 330703 Specdb::NmrOneD 330704 Specdb::NmrOneD 330705 Specdb::NmrOneD 330706 Specdb::NmrOneD 330707 Specdb::NmrOneD 330708 Specdb::NmrOneD 330709 Specdb::NmrOneD 330710 Specdb::NmrOneD 330711 Specdb::NmrOneD 330712 Specdb::NmrOneD 330713 Specdb::NmrOneD 330714 Specdb::NmrOneD 330715 Specdb::NmrOneD 330716 Specdb::NmrOneD 330717 Specdb::NmrOneD 330718 Specdb::NmrOneD 330719 Specdb::NmrOneD 330720 Specdb::NmrOneD 330721 Specdb::MsMs 29216 Specdb::MsMs 29217 Specdb::MsMs 29218 Specdb::MsMs 35774 Specdb::MsMs 35775 Specdb::MsMs 35776 439874 388913 C02995 15703 CPD-1244 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml PTS system maltose- and glucose-specific EIICB component P19642 PTOCB_ECOLI malX http://ecmdb.ca/proteins/P19642.xml Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml PTS system maltose- and glucose-specific EIICB component P19642 PTOCB_ECOLI malX http://ecmdb.ca/proteins/P19642.xml Phosphoenolpyruvic acid + D-Maltose > Maltose 6'-phosphate + Pyruvic acid Protein N(pi)-phospho-L-histidine + D-Maltose <> Protein histidine + Maltose 6'-phosphate R04111