2.0 2012-05-31 13:45:44 -0600 2015-06-03 15:53:45 -0600 ECMDB01124 M2MDB000263 Trehalose 6-phosphate Trehalose-6-phopshate is a phosphorylated form of trehalose. Trehalose is a disaccharide that acts as an osmoprotectant as well as a carbon source in Escherichia coli. At high osmolarity the cells synthesize large amounts of trehalose internally as an osmoprotectant. However, they can also degrade trehalose as the sole source of carbon under both high- and low-osmolarity growth conditions. The modes of trehalose utilization are different under the two conditions. At low osmolarity, trehalose is transported via a trehalose-specific enzyme of the phosphotransferase system, encoded by treB. The trehalose-6-phosphate formed by this enzyme is hydrolyzed to glucose and glucose 6-phosphate by trehalose-6-phosphate hydrolase, encoded by treC. α,α-trehalose 6-phosphate α,α-trehalose 6-phosphoric acid a,a-Trehalose 6-phosphate a,a-Trehalose 6-phosphoric acid a,Alpha'-trehalose 6-phosphate a,Alpha'-trehalose 6-phosphoric acid Alpha,alpha'-Trehalose 6-phosphate alpha,Alpha'-trehalose 6-phosphoric acid Alpha,alpha-Trehalose 6-phosphate alpha,alpha-Trehalose 6-phosphoric acid Trehalose 6-phosphoric acid Trehalose phosphate Trehalose phosphoric acid Trehalose-6-phosphate Trehalose-6-phosphoric acid α,Alpha'-trehalose 6-phosphate α,Alpha'-trehalose 6-phosphoric acid α,α-Trehalose 6-phosphate α,α-Trehalose 6-phosphoric acid C12H23O14P 422.2764 422.082541956 {[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}phosphonic acid α,α'-trehalose 6-phosphate 4484-88-2 OC[C@H]1O[C@H](O[C@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C12H23O14P/c13-1-3-5(14)7(16)9(18)11(24-3)26-12-10(19)8(17)6(15)4(25-12)2-23-27(20,21)22/h3-19H,1-2H2,(H2,20,21,22)/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 LABSPYBHMPDTEL-LIZSDCNHSA-N Solid Cytosol logp -2.42 ALOGPS logs -1.02 ALOGPS solubility 4.06e+01 g/l ALOGPS logp -4.8 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac {[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 422.2764 ChemAxon mono_mass 422.082541956 ChemAxon smiles OC[C@H]1O[C@H](O[C@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C12H23O14P ChemAxon inchi InChI=1S/C12H23O14P/c13-1-3-5(14)7(16)9(18)11(24-3)26-12-10(19)8(17)6(15)4(25-12)2-23-27(20,21)22/h3-19H,1-2H2,(H2,20,21,22)/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 ChemAxon inchikey LABSPYBHMPDTEL-LIZSDCNHSA-N ChemAxon polar_surface_area 236.06 ChemAxon refractivity 79.21 ChemAxon polarizability 35.55 ChemAxon rotatable_bond_count 6 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 Metabolic pathways eco01100 trehalose biosynthesis I TRESYN-PWY trehalose degradation I (low osmolarity) TREDEGLOW-PWY Specdb::CMs 25828 Specdb::CMs 32340 Specdb::CMs 37935 Specdb::CMs 99653 Specdb::CMs 146413 Specdb::CMs 153951 Specdb::CMs 153953 Specdb::CMs 153955 Specdb::CMs 153957 Specdb::CMs 153959 Specdb::CMs 153961 Specdb::CMs 153963 Specdb::CMs 153965 Specdb::CMs 153967 Specdb::CMs 153969 Specdb::CMs 153971 Specdb::CMs 153973 Specdb::CMs 153975 Specdb::CMs 153977 Specdb::CMs 153979 Specdb::CMs 153980 Specdb::CMs 153982 Specdb::CMs 153984 Specdb::CMs 153986 Specdb::CMs 153988 Specdb::NmrOneD 8702 Specdb::NmrOneD 8703 Specdb::NmrOneD 8704 Specdb::NmrOneD 8705 Specdb::NmrOneD 8706 Specdb::NmrOneD 8707 Specdb::NmrOneD 8708 Specdb::NmrOneD 8709 Specdb::NmrOneD 8710 Specdb::NmrOneD 8711 Specdb::NmrOneD 8712 Specdb::NmrOneD 8713 Specdb::NmrOneD 8714 Specdb::NmrOneD 8715 Specdb::NmrOneD 8716 Specdb::NmrOneD 8717 Specdb::NmrOneD 8718 Specdb::NmrOneD 8719 Specdb::NmrOneD 8720 Specdb::NmrOneD 8721 Specdb::MsMs 28577 Specdb::MsMs 28578 Specdb::MsMs 28579 Specdb::MsMs 35135 Specdb::MsMs 35136 Specdb::MsMs 35137 Specdb::MsMs 438557 Specdb::MsMs 438558 Specdb::MsMs 438559 Specdb::MsMs 438560 Specdb::MsMs 438561 Specdb::MsMs 447139 Specdb::MsMs 447140 Specdb::MsMs 447141 Specdb::MsMs 447142 Specdb::MsMs 447143 Specdb::MsMs 447295 Specdb::MsMs 2226299 Specdb::MsMs 2228428 Specdb::MsMs 2420079 Specdb::MsMs 2420080 Specdb::MsMs 2420081 Specdb::MsMs 2545102 Specdb::MsMs 2545103 Specdb::MsMs 2545104 HMDB01124 122336 109086 C00689 18283 TREHALOSE-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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 MacDonald, Donald L.; Wong, Roger Y. K. Chemical synthesis of trehalose 6-phosphate. Biochimica et Biophysica Acta, General Subjects (1964), 86(2), 390-2. Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Trehalose-6-phosphate hydrolase P28904 TREC_ECOLI treC http://ecmdb.ca/proteins/P28904.xml Alpha,alpha-trehalose-phosphate synthase [UDP-forming] P31677 OTSA_ECOLI otsA http://ecmdb.ca/proteins/P31677.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 Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml PTS system trehalose-specific EIIBC component P36672 PTTBC_ECOLI treB http://ecmdb.ca/proteins/P36672.xml Phosphoenolpyruvic acid + Trehalose > Pyruvic acid + Trehalose 6-phosphate TRANS-RXN-168 Glucose 6-phosphate + UDP-Glucose > Hydrogen ion + Trehalose 6-phosphate + Uridine 5'-diphosphate R02737 Water + Trehalose 6-phosphate > Phosphate + Trehalose R02778 TREHALOSEPHOSPHA-RXN Water + Trehalose 6-phosphate > Glucose 6-phosphate + D-Glucose Water + Trehalose 6-phosphate <> D-Glucose + D-Hexose 6-phosphate R06113 UDP-Glucose + Glucose 6-phosphate <> Uridine 5'-diphosphate + Trehalose 6-phosphate R02737 Trehalose 6-phosphate + Water <> Trehalose + Phosphate R02778 Trehalose + Protein N(pi)-phospho-L-histidine <> Trehalose 6-phosphate + Protein histidine R02780 Phosphoenolpyruvic acid + Trehalose > Trehalose 6-phosphate + Pyruvic acid TRANS-RXN-168 Trehalose 6-phosphate + Water > Glucose 6-phosphate + b-D-Glucose TRE6PHYDRO-RXN UDP-Glucose + α-D-glucose 6-phosphate > Hydrogen ion + Uridine 5'-diphosphate + Trehalose 6-phosphate TREHALOSE6PSYN-RXN UDP-Glucose + Glucose 6-phosphate > Uridine 5'-diphosphate + Trehalose 6-phosphate Trehalose 6-phosphate + Water > Trehalose + Inorganic phosphate Trehalose 6-phosphate + Water <> D-Glucose + Glucose 6-phosphate R00837 R06113 UDP-Glucose + Alpha-D-glucose 6-phosphate > Uridine 5'-diphosphate + Trehalose 6-phosphate + Hydrogen ion + Uridine 5'-diphosphate PW_R003513 Trehalose 6-phosphate + Water > Phosphate + α,α-trehalose PW_R003514 α,α-trehalose + HPr - phosphorylated > Trehalose 6-phosphate + HPr PW_RCT000153