2.0 2012-05-31 14:28:45 -0600 2015-06-03 17:19:21 -0600 ECMDB20124 M2MDB000972 beta-D-Glucose 1-phosphate Beta-D-glucose 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Trehalose phosphorylase from Thermoanaerobacter sp. is a glycoside hydrolase family 65 enzyme which catalyzes the reversible breakdown of trehalose [D-glucopyranosyl-alpha(1,1)alpha-D-glucopyranose] to beta-D-glucose 1-phosphate and D-glucose. (PMID 20383018) SgrS is an Hfq-binding small RNA that is induced under glucose phosphate stress in Escherichia coli. (PMID 18650387) .alpha.-D-Glucose, 1-phosphate .alpha.-D-glucose, 1-phosphoric acid 1-O-phosphono-b-D-Glucopyranose 1-O-Phosphono-beta-D-glucopyranose 1-O-phosphono-β-D-Glucopyranose 1-phospho-b-D-Glucopyranose 1-Phospho-beta-D-glucopyranose 1-phospho-β-D-Glucopyranose b-D-Glucopyranose 1-(dihydrogen phosphate) b-D-Glucopyranose 1-(dihydrogen phosphoric acid) b-D-Glucose 1-phosphate b-D-Glucose 1-phosphoric acid Beta-D-Glucopyranose 1-(dihydrogen phosphate) beta-D-Glucopyranose 1-(dihydrogen phosphoric acid) beta-D-Glucose 1-phosphoric acid Cori ester Dol-p-GLC Dolichol monophosphate glucose Dolichol monophosphoric acid glucose Dolichol-D-glucosylmonophosphate Dolichol-D-glucosylmonophosphoric acid Dolichyl monophosphate glucose Dolichyl monophosphoric acid glucose Dolichylglucose phosphate Dolichylglucose phosphoric acid Glucosylphosphodolichol phospho-b-D-Glucoside Phospho-beta-D-glucoside phospho-β-D-Glucoside β-D-Glucopyranose 1-(dihydrogen phosphate) β-D-Glucopyranose 1-(dihydrogen phosphoric acid) β-D-Glucose 1-phosphate β-D-Glucose 1-phosphoric acid C6H13O9P 260.1358 260.029718526 {[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid β-D-glucose 1-phosphate 55607-88-0 [H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OP(O)(O)=O)[C@]1([H])O InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6+/m1/s1 HXXFSFRBOHSIMQ-DVKNGEFBSA-N Cytoplasm Periplasm logp -2.00 ALOGPS logs -0.91 ALOGPS solubility 3.23e+01 g/l ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 1.16 ChemAxon pka_strongest_basic -3 ChemAxon iupac {[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid ChemAxon average_mass 260.1358 ChemAxon mono_mass 260.029718526 ChemAxon smiles [H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OP(O)(O)=O)[C@]1([H])O ChemAxon formula C6H13O9P ChemAxon inchi InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6+/m1/s1 ChemAxon inchikey HXXFSFRBOHSIMQ-DVKNGEFBSA-N ChemAxon polar_surface_area 156.91 ChemAxon refractivity 46.8 ChemAxon polarizability 20.36 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 Specdb::CMs 1083658 Specdb::NmrOneD 330482 Specdb::NmrOneD 330483 Specdb::NmrOneD 330484 Specdb::NmrOneD 330485 Specdb::NmrOneD 330486 Specdb::NmrOneD 330487 Specdb::NmrOneD 330488 Specdb::NmrOneD 330489 Specdb::NmrOneD 330490 Specdb::NmrOneD 330491 Specdb::NmrOneD 330492 Specdb::NmrOneD 330493 Specdb::NmrOneD 330494 Specdb::NmrOneD 330495 Specdb::NmrOneD 330496 Specdb::NmrOneD 330497 Specdb::NmrOneD 330498 Specdb::NmrOneD 330499 Specdb::NmrOneD 330500 Specdb::NmrOneD 330501 Specdb::MsMs 28844 Specdb::MsMs 28845 Specdb::MsMs 28846 Specdb::MsMs 35402 Specdb::MsMs 35403 Specdb::MsMs 35404 122250 109022 C00663 16218 CPD-448 XGP 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 Van Hoorebeke, A., Stout, J., Van der Meeren, R., Kyndt, J., Van Beeumen, J., Savvides, S. N. (2010). "Crystallization and X-ray diffraction studies of inverting trehalose phosphorylase from Thermoanaerobacter sp." Acta Crystallogr Sect F Struct Biol Cryst Commun 66:442-447. 20383018 Maki, K., Uno, K., Morita, T., Aiba, H. (2008). "RNA, but not protein partners, is directly responsible for translational silencing by a bacterial Hfq-binding small RNA." Proc Natl Acad Sci U S A 105:10332-10337. 18650387 Putative beta-phosphoglucomutase P77366 PGMB_ECOLI ycjU http://ecmdb.ca/proteins/P77366.xml beta-D-Glucose 1-phosphate <> beta-D-Glucose 6-phosphate R02728 Glucose 1-phosphate > beta-D-Glucose 1-phosphate RXN-10639 beta-D-Glucose 1-phosphate Glucose 6-phosphate BETA-PHOSPHOGLUCOMUTASE-RXN beta-D-Glucose 1-phosphate > beta-D-Glucose 6-phosphate