2.0 2015-09-08 17:49:07 -0600 2015-09-08 17:49:07 -0600 ECMDB24082 M2MDB006199 Amylose C14H26O11 370.3496 370.147511674 5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}-6-(hydroxymethyl)-2-methoxyoxane-3,4-diol 5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}-6-(hydroxymethyl)-2-methoxyoxane-3,4-diol COC1OC(CO)C(OC2OC(CO)C(OC)C(O)C2O)C(O)C1O InChI=1S/C14H26O11/c1-21-11-5(3-15)24-14(10(20)7(11)17)25-12-6(4-16)23-13(22-2)9(19)8(12)18/h5-20H,3-4H2,1-2H3 PTHCMJGKKRQCBF-UHFFFAOYSA-N logp -2.41 ALOGPS logs -0.04 ALOGPS solubility 3.39e+02 g/l ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 11.97 ChemAxon pka_strongest_basic -3 ChemAxon iupac 5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}-6-(hydroxymethyl)-2-methoxyoxane-3,4-diol ChemAxon average_mass 370.3496 ChemAxon mono_mass 370.147511674 ChemAxon smiles COC1OC(CO)C(OC2OC(CO)C(OC)C(O)C2O)C(O)C1O ChemAxon formula C14H26O11 ChemAxon inchi InChI=1S/C14H26O11/c1-21-11-5(3-15)24-14(10(20)7(11)17)25-12-6(4-16)23-13(22-2)9(19)8(12)18/h5-20H,3-4H2,1-2H3 ChemAxon inchikey PTHCMJGKKRQCBF-UHFFFAOYSA-N ChemAxon polar_surface_area 167.53 ChemAxon refractivity 77.84 ChemAxon polarizability 35.79 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 11 ChemAxon donor_count 6 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 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 Specdb::CMs 14092 Specdb::CMs 42783 Specdb::CMs 132982 Specdb::CMs 140716 Specdb::NmrOneD 112198 Specdb::NmrOneD 112199 Specdb::NmrOneD 112200 Specdb::NmrOneD 112201 Specdb::NmrOneD 112202 Specdb::NmrOneD 112203 Specdb::NmrOneD 112204 Specdb::NmrOneD 112205 Specdb::NmrOneD 112206 Specdb::NmrOneD 112207 Specdb::NmrOneD 112208 Specdb::NmrOneD 112209 Specdb::NmrOneD 112210 Specdb::NmrOneD 112211 Specdb::NmrOneD 112212 Specdb::NmrOneD 112213 Specdb::NmrOneD 112214 Specdb::NmrOneD 112215 Specdb::NmrOneD 112216 Specdb::NmrOneD 112217 Specdb::MsMs 24590 Specdb::MsMs 24591 Specdb::MsMs 24592 Specdb::MsMs 31148 Specdb::MsMs 31149 Specdb::MsMs 31150 Specdb::MsMs 2322805 Specdb::MsMs 2322806 Specdb::MsMs 2322807 Specdb::MsMs 2616231 Specdb::MsMs 2616232 Specdb::MsMs 2616233 Maltodextrin phosphorylase P00490 PHSM_ECOLI malP http://ecmdb.ca/proteins/P00490.xml 1,4-alpha-glucan-branching enzyme P07762 GLGB_ECOLI glgB http://ecmdb.ca/proteins/P07762.xml Glycogen synthase P0A6U8 GLGA_ECOLI glgA http://ecmdb.ca/proteins/P0A6U8.xml Alpha-D-glucose 1-phosphate + Amylose <> Phosphate + Glycogen PW_R003507 Amylose <> Glycogen PW_R003508 ADP-Glucose + Amylose <> Amylose + Adenosine diphosphate + ADP PW_R003512 ADP-Glucose + Amylose <> Amylose + Adenosine diphosphate + ADP PW_R003512