2.0 2012-05-31 14:32:35 -0600 2015-06-03 17:19:31 -0600 ECMDB20196 M2MDB001042 Sucrose-6-phosphate Sucrose-6-phosphate is a member of the chemical class known as Mixed Pentose/Hexose Disaccharides. These are disaccharides containing both an hexose and a pentose. 6-O-Phosphonosucrose 6-Phosphosucrose Sucrose 6-phosphate Sucrose 6-phosphoric acid Sucrose 6^F-phosphate Sucrose 6F-phosphate Sucrose 6f-phosphoric acid Sucrose 6F-phosphoric acid Sucrose-6-P Sucrose-6-phosphoric acid Sucrose-6F-P C12H23O14P 422.2764 422.082541956 {[(2R,3S,4S,5R,6R)-6-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}phosphonic acid sucrose-6-phosphate 22372-29-8 OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O InChI=1S/C12H23O14P/c13-1-4-7(16)10(19)12(3-14,25-4)26-11-9(18)8(17)6(15)5(24-11)2-23-27(20,21)22/h4-11,13-19H,1-3H2,(H2,20,21,22)/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1 WQQSIXKPRAUZJL-UGDNZRGBSA-N Cytosol logp -2.75 ALOGPS logs -1.03 ALOGPS solubility 3.90e+01 g/l ALOGPS logp -4.7 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac {[(2R,3S,4S,5R,6R)-6-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 422.2764 ChemAxon mono_mass 422.082541956 ChemAxon smiles OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O ChemAxon formula C12H23O14P ChemAxon inchi InChI=1S/C12H23O14P/c13-1-4-7(16)10(19)12(3-14,25-4)26-11-9(18)8(17)6(15)5(24-11)2-23-27(20,21)22/h4-11,13-19H,1-3H2,(H2,20,21,22)/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1 ChemAxon inchikey WQQSIXKPRAUZJL-UGDNZRGBSA-N ChemAxon polar_surface_area 236.06 ChemAxon refractivity 79.65 ChemAxon polarizability 35.66 ChemAxon rotatable_bond_count 7 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 Phosphotransferase system (PTS) ec02060 Specdb::CMs 1083476 Specdb::NmrOneD 294735 Specdb::NmrOneD 294736 Specdb::NmrOneD 294737 Specdb::NmrOneD 294738 Specdb::NmrOneD 294739 Specdb::NmrOneD 294740 Specdb::NmrOneD 294741 Specdb::NmrOneD 294742 Specdb::NmrOneD 294743 Specdb::NmrOneD 294744 Specdb::NmrOneD 294745 Specdb::NmrOneD 294746 Specdb::NmrOneD 294747 Specdb::NmrOneD 294748 Specdb::NmrOneD 294749 Specdb::NmrOneD 294750 Specdb::NmrOneD 294751 Specdb::NmrOneD 294752 Specdb::NmrOneD 294753 Specdb::NmrOneD 294754 Specdb::MsMs 24797 Specdb::MsMs 24798 Specdb::MsMs 24799 Specdb::MsMs 31355 Specdb::MsMs 31356 Specdb::MsMs 31357 Specdb::MsMs 3597854 Specdb::MsMs 3597855 Specdb::MsMs 3597856 Specdb::MsMs 3597857 Specdb::MsMs 3597858 Specdb::MsMs 3597859 644101 559141 C16688 SUCROSE-6P Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 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 Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml PTS system N-acetylmuramic acid-specific EIIBC component P77272 PTYBC_ECOLI murP http://ecmdb.ca/proteins/P77272.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml PTS system N-acetylmuramic acid-specific EIIBC component P77272 PTYBC_ECOLI murP http://ecmdb.ca/proteins/P77272.xml Phosphoenolpyruvic acid + Sucrose > Pyruvic acid + Sucrose-6-phosphate