2.0 2012-05-31 09:56:13 -0600 2015-09-13 12:56:05 -0600 ECMDB00055 M2MDB000018 Cellobiose Cellobiose is a disaccharide consisting of two glucose units in a beta (1-4) glycosidic linkage. It is an intermediate of starch and sucrose metabolism. It is formed through the action of endo-1,4-D-glucanase and converted to beta-D-glucose by beta-D-glucoside glucohydrolase (EC:3.2.1.21). (KEGG) 4-&beta;-D-glucopyranosyl-D-glucopyranose 4-(b-D-Glucosido)-D-glucose 4-(b-delta-Glucosido)-delta-glucose 4-(b-δ-glucosido)-δ-Glucose 4-(beta-D-Glucosido)-D-glucose 4-(beta-delta-Glucosido)-delta-glucose 4-(β-D-glucosido)-D-Glucose 4-(β-δ-glucosido)-δ-Glucose 4-b-D-Glucopyranosyl-D-glucopyranose 4-b-delta-Glucopyranosyl-delta-glucopyranose 4-b-δ-Glucopyranosyl-δ-glucopyranose 4-beta-D-Glucopyranosyl-D-glucopyranose 4-beta-delta-Glucopyranosyl-delta-glucopyranose 4-O-b-D-Glucopyranosyl-D-glucose 4-O-b-delta-Glucopyranosyl-delta-glucose 4-O-b-δ-Glucopyranosyl-δ-glucose 4-O-beta-D-Glucopyranosyl-D-glucose 4-O-beta-delta-Glucopyranosyl-delta-glucose 4-O-β-D-Glucopyranosyl-D-glucose 4-O-β-δ-Glucopyranosyl-δ-glucose 4-β-D-Glucopyranosyl-D-glucopyranose 4-β-δ-Glucopyranosyl-δ-glucopyranose Cellobiose Cellose D-(+)-Cellobiose D-Cellobiose D-Glucosyl-b-(1-4)-D-glucose D-Glucosyl-b-(1->4)-D-glucose D-Glucosyl-beta-(1-4)-D-glucose D-Glucosyl-beta-(1->4)-D-glucose D-Glucosyl-β-(1-4)-D-glucose D-Glucosyl-β-(1->4)-D-glucose Delta-(+)-Cellobiose Delta-Cellobiose delta-Glucosyl-b-(1-4)-delta-glucose delta-Glucosyl-b-(1->4)-delta-glucose Delta-Glucosyl-beta-(1-4)-delta-glucose Delta-Glucosyl-beta-(1->4)-delta-glucose δ-(+)-Cellobiose δ-Cellobiose δ-Glucosyl-b-(1-4)-δ-glucose δ-Glucosyl-b-(1->4)-δ-glucose δ-Glucosyl-β-(1-4)-δ-glucose δ-Glucosyl-β-(1->4)-δ-glucose C12H22O11 342.2965 342.116211546 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol β-cellobiose 528-50-7 OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8-,9-,10-,11-,12+/m1/s1 GUBGYTABKSRVRQ-QRZGKKJRSA-N Solid Cytoplasm Periplasm logp -3.01 ALOGPS logs 0.23 ALOGPS solubility 5.86e+02 g/l ALOGPS melting_point 229-230 oC logp -4.7 ChemAxon pka_strongest_acidic 11.25 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-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]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C12H22O11 ChemAxon inchi InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8-,9-,10-,11-,12+/m1/s1 ChemAxon inchikey GUBGYTABKSRVRQ-QRZGKKJRSA-N ChemAxon polar_surface_area 189.53 ChemAxon refractivity 68.34 ChemAxon polarizability 31.08 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 Specdb::CMs 2066 Specdb::CMs 2084 Specdb::CMs 2125 Specdb::CMs 13823 Specdb::CMs 31995 Specdb::CMs 31996 Specdb::CMs 37269 Specdb::CMs 148277 Specdb::CMs 148279 Specdb::CMs 148281 Specdb::CMs 148283 Specdb::CMs 148284 Specdb::CMs 148287 Specdb::CMs 148289 Specdb::CMs 148291 Specdb::CMs 148293 Specdb::CMs 160559 Specdb::CMs 279667 Specdb::CMs 1048603 Specdb::CMs 1048605 Specdb::CMs 1048607 Specdb::CMs 1048609 Specdb::CMs 1048611 Specdb::CMs 1048613 Specdb::CMs 1048615 Specdb::NmrOneD 1057 Specdb::NmrOneD 5472 Specdb::NmrOneD 5473 Specdb::NmrOneD 5474 Specdb::NmrOneD 5475 Specdb::NmrOneD 5476 Specdb::NmrOneD 5477 Specdb::NmrOneD 5478 Specdb::NmrOneD 5479 Specdb::NmrOneD 5480 Specdb::NmrOneD 5481 Specdb::NmrOneD 5482 Specdb::NmrOneD 5483 Specdb::NmrOneD 5484 Specdb::NmrOneD 5485 Specdb::NmrOneD 5486 Specdb::NmrOneD 5487 Specdb::NmrOneD 5488 Specdb::NmrOneD 5489 Specdb::NmrOneD 5490 Specdb::NmrOneD 5491 Specdb::MsMs 87 Specdb::MsMs 88 Specdb::MsMs 89 Specdb::MsMs 179643 Specdb::MsMs 179644 Specdb::MsMs 179645 Specdb::MsMs 181977 Specdb::MsMs 181978 Specdb::MsMs 181979 Specdb::MsMs 2240383 Specdb::MsMs 2244580 Specdb::MsMs 2245550 Specdb::MsMs 2246638 Specdb::MsMs 2247633 Specdb::MsMs 2248760 Specdb::MsMs 2249639 Specdb::MsMs 2250799 Specdb::MsMs 2251590 Specdb::MsMs 2844788 Specdb::MsMs 2844789 Specdb::MsMs 2844790 Specdb::MsMs 2860471 Specdb::MsMs 2860472 Specdb::MsMs 2860473 Specdb::NmrTwoD 944 Specdb::NmrTwoD 1115 HMDB00055 439178 10261 C00185 17057 CELLOBIOSE CBI Cellobiose Keseler, I. 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Kokai Tokkyo Koho (2006), 20pp. CODEN: JKXXAF JP 2006204294 A 20060810 CAN 145:187210 AN 2006:786561 http://hmdb.ca/system/metabolites/msds/000/000/040/original/HMDB00055.pdf?1358463244 PTS system arbutin-, cellobiose-, and salicin-specific EIIBC component P24241 PTIBC_ECOLI ascF http://ecmdb.ca/proteins/P24241.xml Periplasmic beta-glucosidase P33363 BGLX_ECOLI bglX http://ecmdb.ca/proteins/P33363.xml Endoglucanase P37651 GUN_ECOLI bcsZ http://ecmdb.ca/proteins/P37651.xml PTS system arbutin-, cellobiose-, and salicin-specific EIIBC component P24241 PTIBC_ECOLI ascF http://ecmdb.ca/proteins/P24241.xml Sugar efflux transporter C P31436 SETC_ECOLI setC http://ecmdb.ca/proteins/P31436.xml Cellobiose + Water <>2 b-D-Glucose R00026 Cellulose + Water <> Cellulose + Cellobiose R02886 Phosphoenolpyruvic acid + Cellobiose > Cellobiose-6-phosphate + Pyruvic acid TRANS-RXN-155 Cellobiose + Water <>2 b-D-Glucose