2.0 2012-07-30 14:55:22 -0600 2015-09-13 12:56:15 -0600 ECMDB21341 M2MDB001740 Glycogen Glycogen is a highly branched glucose polymer. It is formed of small chains of 8 to 12 glucose molecules linked together with (1->4) bonds. These small chains are in turn linked together with (1->6) bonds. A single molecule of glycogen can be made of up to 120,000 molecules of glucose. It is stored in the form of granules in the cytosol. (EcoCyc) Glycogen only has one reducing end and a large number of non-reducing ends with a free hydroxyl group at carbon 4. The glycogen granules contain both glycogen and the enzymes of glycogen synthesis (glycogenesis) and degradation (glycogenolysis). The enzymes are nested between the outer branches of the glycogen molecules and act on the non-reducing ends. Therefore, the many non-reducing end-branches of glycogen facilitate its rapid synthesis and breakdown. (HMDB) Animal starch Glycogen Liver starch Lyoglycogen Phytoglycogen C24H42O21 666.5777 666.221858406 (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-2-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-2-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol 9005-79-2 OC[C@H]1O[C@H](OC[C@H]2O[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]3CO)[C@H](O)[C@@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C24H42O21/c25-1-5-9(28)11(30)16(35)22(41-5)39-4-8-20(45-23-17(36)12(31)10(29)6(2-26)42-23)14(33)18(37)24(43-8)44-19-7(3-27)40-21(38)15(34)13(19)32/h5-38H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15-,16-,17-,18-,19-,20-,21+,22+,23-,24-/m1/s1 BYSGBSNPRWKUQH-UJDJLXLFSA-N Solid Cytosol logp -2.67 ALOGPS logs -0.29 ALOGPS solubility 3.43e+02 g/l ALOGPS melting_point 270-280 oC logp -8.2 ChemAxon pka_strongest_acidic 11.19 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-2-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol ChemAxon average_mass 666.5777 ChemAxon mono_mass 666.221858406 ChemAxon smiles OC[C@H]1O[C@H](OC[C@H]2O[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]3CO)[C@H](O)[C@@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C24H42O21 ChemAxon inchi InChI=1S/C24H42O21/c25-1-5-9(28)11(30)16(35)22(41-5)39-4-8-20(45-23-17(36)12(31)10(29)6(2-26)42-23)14(33)18(37)24(43-8)44-19-7(3-27)40-21(38)15(34)13(19)32/h5-38H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15-,16-,17-,18-,19-,20-,21+,22+,23-,24-/m1/s1 ChemAxon inchikey BYSGBSNPRWKUQH-UJDJLXLFSA-N ChemAxon polar_surface_area 347.83 ChemAxon refractivity 133.16 ChemAxon polarizability 61.39 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 21 ChemAxon donor_count 14 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 686075 Specdb::CMs 686076 Specdb::CMs 686077 Specdb::CMs 686078 Specdb::CMs 686079 Specdb::CMs 686080 Specdb::CMs 686081 Specdb::CMs 686082 Specdb::CMs 686083 Specdb::CMs 686084 Specdb::CMs 686085 Specdb::CMs 686086 Specdb::CMs 686087 Specdb::CMs 686088 Specdb::CMs 686089 Specdb::CMs 686090 Specdb::CMs 686091 Specdb::CMs 686092 Specdb::CMs 686093 Specdb::CMs 686094 Specdb::CMs 686095 Specdb::CMs 686096 Specdb::CMs 686097 Specdb::CMs 686098 Specdb::CMs 686099 Specdb::NmrOneD 1526 Specdb::NmrOneD 4984 Specdb::MsMs 26375 Specdb::MsMs 26376 Specdb::MsMs 26377 Specdb::MsMs 32933 Specdb::MsMs 32934 Specdb::MsMs 32935 Specdb::MsMs 2681565 Specdb::MsMs 2681566 Specdb::MsMs 2681567 Specdb::MsMs 3026646 Specdb::MsMs 3026647 Specdb::MsMs 3026648 Specdb::NmrTwoD 1037 Specdb::NmrTwoD 1472 HMDB00757 439177 388322 C00182 28087 Glycogens Glycogen Price TB, Laurent D, Petersen KF: 13C/31P NMR studies on the role of glucose transport/phosphorylation in human glycogen supercompensation. 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Epub 2005 Aug 23. 16118338 http://hmdb.ca/system/metabolites/msds/000/000/676/original/HMDB00757.pdf?1358894436 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 Glycogen phosphorylase P0AC86 PHSG_ECOLI glgP http://ecmdb.ca/proteins/P0AC86.xml Glycogen debranching enzyme P15067 GLGX_ECOLI glgX http://ecmdb.ca/proteins/P15067.xml Glycogen + Phosphate > Glucose 1-phosphate ADP-Glucose > ADP + Glycogen + Hydrogen ion branching glycogen > Glycogen Glycogen > branching glycogen a 1,4-&alpha;-D-glucan <> Glycogen GLYCOGEN-BRANCH-RXN Glycogen + Phosphate <> a limit dextrin + Glucose 1-phosphate GLYCOPHOSPHORYL-RXN Alpha-D-glucose 1-phosphate + Amylose <> Phosphate + Glycogen PW_R003507 Amylose <> Glycogen PW_R003508 Glycogen <> α,α-trehalose PW_R003515 Glycogen + Phosphate > Alpha-D-glucose 1-phosphate + Dextrin + Dextrin PW_R003520