2.0 2012-05-31 13:02:50 -0600 2015-09-13 12:56:09 -0600 ECMDB00975 M2MDB000214 Trehalose Trehalose, also known as mycose, is a 1-alpha (disaccharide) sugar found extensively but not abundantly in nature. It is thought to be implicated in anhydrobiosis - the ability of plants and animals to withstand prolonged periods of desiccation. The sugar is thought to form a gel phase as cells dehydrate, which prevents disruption of internal cell organelles by effectively splinting them in position. Rehydration then allows normal cellular activity to be resumed without the major, generally lethal damage that would normally follow a dehydration/reyhdration cycle.Trehalose is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond giving it the name of alpha-D-glucopyranoglucopyranosyl-1,1-alpha-D-glucopyranoside. The bonding makes trehalose very resistant to acid hydrolysis, and therefore stable in solution at high temperatures even under acidic conditions. The bonding also keeps non-reducing sugars in closed-ring form, such that the aldehyde or ketone end-groups do not bind to the lysine or arginine residues of proteins (a process called glycation). The enzyme trehalase breaks it into two glucose molecules. &alpha;,&alpha;-trehalose a,a-Trehalose Alpha,alpha-Trehalose D-Trehalose D-Trehalose-anhydrous Delta-Trehalose-anhydrous α,α-Trehalose δ-Trehalose-anhydrous 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 99-20-7 OC[C@H]1O[C@H](O[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/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/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 HDTRYLNUVZCQOY-LIZSDCNHSA-N Solid Cytosol Extra-organism Periplasm logp -2.98 ALOGPS logs 0.24 ALOGPS solubility 5.92e+02 g/l ALOGPS melting_point 203 oC 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 OC[C@H]1O[C@H](O[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 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/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 ChemAxon inchikey HDTRYLNUVZCQOY-LIZSDCNHSA-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 Phosphotransferase system (PTS) ec02060 ABC transporters ec02010 Metabolic pathways eco01100 trehalose degradation II (trehalase) PWY0-1182 trehalose degradation VI (periplasmic) PWY0-1466 trehalose biosynthesis I TRESYN-PWY 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 HMDB00975 1143 7149 C01083 16551 TREHALOSE TRE Trehalose Keseler, I. 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Agricultural and Biological Chemistry (1985), 49(7), 2113-18. http://hmdb.ca/system/metabolites/msds/000/000/876/original/HMDB00975.pdf?1358461601 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml 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 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 Sugar efflux transporter C P31436 SETC_ECOLI setC http://ecmdb.ca/proteins/P31436.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Phosphoenolpyruvic acid + Trehalose > Pyruvic acid + Trehalose 6-phosphate TRANS-RXN-168 Water + Trehalose >2 D-Glucose Water + Trehalose 6-phosphate > Phosphate + Trehalose R02778 TREHALOSEPHOSPHA-RXN Trehalose + Water <>2 D-Glucose R00010 Trehalose 6-phosphate + Water <> Trehalose + Phosphate R02778 Trehalose + Protein N(pi)-phospho-L-histidine <> Trehalose 6-phosphate + Protein histidine R02780 Starch <> Trehalose R09995 Phosphoenolpyruvic acid + Trehalose > Trehalose 6-phosphate + Pyruvic acid TRANS-RXN-168 Trehalose + Water > b-D-Glucose + D-Glucose TREHALA-RXN Trehalose 6-phosphate + Water > Trehalose + Inorganic phosphate Trehalose + Water > b-D-Glucose + alpha-D-Glucose Trehalose + Water <> b-D-Glucose + alpha-D-Glucose R00010 R06103 Water + Trehalose >2 D-Glucose Trehalose + Water <>2 D-Glucose