2.0 2015-09-08 17:50:27 -0600 2015-09-08 17:50:27 -0600 ECMDB24256 M2MDB006373 α,α-trehalose C12H22O11 342.2965 342.116211546 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol α,α'-trehalose OCC1OC(OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O InChI=1S/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2 HDTRYLNUVZCQOY-UHFFFAOYSA-N logp -2.98 ALOGPS logs 0.24 ALOGPS solubility 5.92e+02 g/l ALOGPS logp -4.7 ChemAxon pka_strongest_acidic 11.91 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol ChemAxon average_mass 342.2965 ChemAxon mono_mass 342.116211546 ChemAxon smiles OCC1OC(OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O ChemAxon formula C12H22O11 ChemAxon inchi InChI=1S/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2 ChemAxon inchikey HDTRYLNUVZCQOY-UHFFFAOYSA-N ChemAxon polar_surface_area 189.53 ChemAxon refractivity 68.34 ChemAxon polarizability 31.14 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 11 ChemAxon donor_count 8 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 Trehalose Degradation I (low osmolarity) While E. coli only synthesizes trehalose under conditions of high osmolarity, it can degrade the sugar under conditions of both low and high osmolarity and can utilize it as the sole carbon source. Different pathways are employed under different osmolarity conditions. The cell only synthesizes trehalose under high-osmolarity conditions. Therefore, the only source of trehalose under low-osmolarity conditions is external. Utilization of trehalose is induced by the presence of trehalose in the medium. Trehalose is imported into the cell by the trehalose PTS permease, which is composed of the EIIAGlc of the glucose PTS and a trehalose-specific EIITre. Trehalose is phosphorylated during transport and enters the cytoplasm as trehalose-6-phosphate. The resulting trehalose-6-phosphate is then hydrolyzed by trehalose-6-phosphate hydrolase, yielding glucose and glucose-6-phosphate. The free glucose is phosphorylated further by glucokinase into a second molecule of glucose-6-phosphate, and both glucose-6-phosphate moieties enter glycolysis. (EcoCyc) PW002097 Metabolic trehalose biosynthesis I Under conditions of elevated osmotic strength, E. coli can regulate the osmotic strength of the cytoplasm by accumulating K+ ions and some organic molecules, commonly called osmoprotectants or compatible solutes. The preferred osmoprotectant of E. coli is glycine betaine. However, its synthesis relies on an external supply of proline, betaines, or choline. When these compounds are not available, a cell can achieve a moderate level of osmotic tolerance by accumulation of glutamate and trehalose. E. coli synthesizes and accumulates trehalose when exposed to osmotic stress and low temperatures. It is synthesized from UDP-glucose and glucose-6-phosphate via trehalose-6-phosphate, by the action of two enzymes, trehalose-6-phosphate synthase and trehalose-6-phosphate phosphatase. Expression of both genes encoding the two enzymes, otsA and otsB, is osmotically regulated. Transcription from these genes increases during osmotic stress and cold shock and when the cells enter stationary phase, and requires the stress sigma factor RpoS. Synthesis of trehalose is also stimulated directly by K+ ion-dependent activation of trehalose-6-phosphate synthase enzyme. Under osmotic stress, E. coli overproduces trehalose, some of which is excreted to the periplasmic space. Once there, it is degraded by the periplasmic trehalase. This process was named "a futile cycle for controlling the cytoplasmic level of trehalose". (EcoCyc) PW002088 Metabolic Specdb::CMs 689 Specdb::CMs 690 Specdb::CMs 691 Specdb::CMs 692 Specdb::CMs 693 Specdb::CMs 694 Specdb::CMs 695 Specdb::CMs 696 Specdb::CMs 697 Specdb::CMs 2094 Specdb::CMs 2607 Specdb::CMs 30183 Specdb::CMs 30278 Specdb::CMs 30279 Specdb::CMs 30280 Specdb::CMs 30281 Specdb::CMs 30282 Specdb::CMs 30283 Specdb::CMs 30702 Specdb::CMs 30780 Specdb::CMs 31273 Specdb::CMs 32348 Specdb::CMs 37872 Specdb::CMs 137739 Specdb::CMs 145473 Specdb::EiMs 1987 Specdb::NmrOneD 1289 Specdb::NmrOneD 1627 Specdb::NmrOneD 4720 Specdb::NmrOneD 8142 Specdb::NmrOneD 8143 Specdb::NmrOneD 8144 Specdb::NmrOneD 8145 Specdb::NmrOneD 8146 Specdb::NmrOneD 8147 Specdb::NmrOneD 8148 Specdb::NmrOneD 8149 Specdb::NmrOneD 8150 Specdb::NmrOneD 8151 Specdb::NmrOneD 8152 Specdb::NmrOneD 8153 Specdb::NmrOneD 8154 Specdb::NmrOneD 8155 Specdb::NmrOneD 8156 Specdb::NmrOneD 8157 Specdb::NmrOneD 8158 Specdb::NmrOneD 8159 Specdb::NmrOneD 8160 Specdb::NmrOneD 8161 Specdb::NmrOneD 166427 Specdb::MsMs 1372 Specdb::MsMs 1373 Specdb::MsMs 1374 Specdb::MsMs 5023 Specdb::MsMs 5024 Specdb::MsMs 178527 Specdb::MsMs 178528 Specdb::MsMs 178529 Specdb::MsMs 180846 Specdb::MsMs 180847 Specdb::MsMs 180848 Specdb::MsMs 439058 Specdb::MsMs 440059 Specdb::MsMs 447544 Specdb::MsMs 448006 Specdb::MsMs 2231894 Specdb::MsMs 2232292 Specdb::MsMs 2234330 Specdb::MsMs 2234630 Specdb::MsMs 2236495 Specdb::MsMs 2236868 Specdb::MsMs 2244854 Specdb::MsMs 2245273 Specdb::MsMs 2246894 Specdb::MsMs 2247386 Specdb::NmrTwoD 1051 Specdb::NmrTwoD 1568 Periplasmic trehalase P13482 TREA_ECOLI treA http://ecmdb.ca/proteins/P13482.xml Trehalose-phosphate phosphatase P31678 OTSB_ECOLI otsB http://ecmdb.ca/proteins/P31678.xml PTS system trehalose-specific EIIBC component P36672 PTTBC_ECOLI treB http://ecmdb.ca/proteins/P36672.xml Cytoplasmic trehalase P62601 TREF_ECOLI treF http://ecmdb.ca/proteins/P62601.xml Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml Glycogen debranching enzyme P15067 GLGX_ECOLI glgX http://ecmdb.ca/proteins/P15067.xml PTS system trehalose-specific EIIBC component P36672 PTTBC_ECOLI treB http://ecmdb.ca/proteins/P36672.xml Trehalose 6-phosphate + Water > Phosphate + α,α-trehalose PW_R003514 Glycogen <> α,α-trehalose PW_R003515 α,α-trehalose + Water > alpha-D-Glucose + Beta-D-Glucose + b-D-Glucose PW_R003516 α,α-trehalose + HPr - phosphorylated > Trehalose 6-phosphate + HPr PW_RCT000153 alpha,alpha-Trehalose 6-phosphate + Water > α,α-trehalose + Phosphate PW_R006094 α,α-trehalose + HPr - phosphorylated > alpha,alpha-Trehalose 6-phosphate + HPr PW_RCT000193