2.0 2012-05-31 13:48:37 -0600 2015-09-13 12:56:10 -0600 ECMDB01262 M2MDB000315 Maltotriose Maltotriose is a member of the chemical class known as Trihexoses. These are trisaccharides containing three hexose carbohydrates. In E. coli, maltotriose is an intermediate involved in degradation of glycogen to glucose. (Ecocyc) 4-O-(4-O-Hexopyranosylhexopyranosyl)hexose Amylotriose D-(+)-Maltotriose Delta-(+)-Maltotriose Maltotriose O-a-D-Glucopyranosyl-(1b94)-O-a-D-glucopyranosyl-(1b94)-O-a-D-glucose O-a-delta-Glucopyranosyl-(1b94)-O-a-delta-glucopyranosyl-(1b94)-O-a-delta-glucose O-a-δ-Glucopyranosyl-(1b94)-O-a-δ-glucopyranosyl-(1b94)-O-a-δ-glucose O-alpha-D-Glucopyranosyl-(1beta94)-O-alpha-D-glucopyranosyl-(1beta94)-O-alpha-D-glucose O-alpha-delta-Glucopyranosyl-(1beta94)-O-alpha-delta-glucopyranosyl-(1beta94)-O-alpha-delta-glucose O-α-D-Glucopyranosyl-(1β94)-O-α-D-glucopyranosyl-(1β94)-O-α-D-glucose O-α-δ-Glucopyranosyl-(1β94)-O-α-δ-glucopyranosyl-(1β94)-O-α-δ-glucose δ-(+)-Maltotriose C18H32O16 504.4371 504.169034976 (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol maltotriose 1109-28-0 OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C18H32O16/c19-1-4-7(22)8(23)12(27)17(31-4)34-15-6(3-21)32-18(13(28)10(15)25)33-14-5(2-20)30-16(29)11(26)9(14)24/h4-29H,1-3H2/t4-,5-,6-,7-,8+,9-,10-,11-,12-,13-,14-,15-,16?,17-,18-/m1/s1 FYGDTMLNYKFZSV-DZOUCCHMSA-N Solid Cytosol Extra-organism Periplasm logp -2.74 ALOGPS logs 0.04 ALOGPS solubility 5.54e+02 g/l ALOGPS logp -6.5 ChemAxon pka_strongest_acidic 11.22 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol ChemAxon average_mass 504.4371 ChemAxon mono_mass 504.169034976 ChemAxon smiles OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C18H32O16 ChemAxon inchi InChI=1S/C18H32O16/c19-1-4-7(22)8(23)12(27)17(31-4)34-15-6(3-21)32-18(13(28)10(15)25)33-14-5(2-20)30-16(29)11(26)9(14)24/h4-29H,1-3H2/t4-,5-,6-,7-,8+,9-,10-,11-,12-,13-,14-,15-,16?,17-,18-/m1/s1 ChemAxon inchikey FYGDTMLNYKFZSV-DZOUCCHMSA-N ChemAxon polar_surface_area 268.68 ChemAxon refractivity 100.75 ChemAxon polarizability 46.65 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 16 ChemAxon donor_count 11 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 Porphyrin and chlorophyll metabolism ec00860 glycogen degradation I GLYCOCAT-PWY Specdb::CMs 722 Specdb::CMs 723 Specdb::CMs 724 Specdb::CMs 725 Specdb::CMs 726 Specdb::CMs 727 Specdb::CMs 12583 Specdb::CMs 31916 Specdb::CMs 31917 Specdb::CMs 37997 Specdb::CMs 168767 Specdb::CMs 168769 Specdb::CMs 168771 Specdb::CMs 168774 Specdb::CMs 168776 Specdb::CMs 168778 Specdb::CMs 168780 Specdb::CMs 168782 Specdb::CMs 168784 Specdb::CMs 168786 Specdb::CMs 168789 Specdb::CMs 168791 Specdb::CMs 168793 Specdb::CMs 168795 Specdb::CMs 168798 Specdb::NmrOneD 1673 Specdb::NmrOneD 87632 Specdb::NmrOneD 87633 Specdb::NmrOneD 87634 Specdb::NmrOneD 87635 Specdb::NmrOneD 87636 Specdb::NmrOneD 87637 Specdb::NmrOneD 87638 Specdb::NmrOneD 87639 Specdb::NmrOneD 87640 Specdb::NmrOneD 87641 Specdb::NmrOneD 87642 Specdb::NmrOneD 87643 Specdb::NmrOneD 87644 Specdb::NmrOneD 87645 Specdb::NmrOneD 87646 Specdb::NmrOneD 87647 Specdb::NmrOneD 87648 Specdb::NmrOneD 87649 Specdb::NmrOneD 87650 Specdb::NmrOneD 87651 Specdb::MsMs 5167 Specdb::MsMs 5168 Specdb::MsMs 2226735 Specdb::MsMs 2231378 Specdb::MsMs 2232848 Specdb::MsMs 2233789 Specdb::MsMs 2235136 Specdb::MsMs 2255878 Specdb::MsMs 1494 Specdb::MsMs 1495 Specdb::MsMs 1496 Specdb::MsMs 2228010 Specdb::MsMs 2229052 Specdb::MsMs 2230382 Specdb::MsMs 334234 Specdb::MsMs 334235 Specdb::MsMs 334236 Specdb::MsMs 2891532 Specdb::MsMs 2891533 Specdb::MsMs 2891534 Specdb::MsMs 293710 Specdb::MsMs 293711 Specdb::MsMs 293712 Specdb::MsMs 2813576 Specdb::MsMs 2813577 Specdb::NmrTwoD 1614 HMDB01262 439586 388669 C01835 27931 MALTOTRIOSE 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 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 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Lingstrom P, Birkhed D, Granfeldt Y, Bjorck I: pH measurements of human dental plaque after consumption of starchy foods using the microtouch and the sampling method. Caries Res. 1993;27(5):394-401. 8242677 Yuge O, Morio M, Fukui T, Fujii K, Kikuchi H, Takahashi S: Maltotriose and maltotetraose excreted in urine following intravenous administration of maltose to human volunteers. Jpn J Surg. 1983 Jul;13(4):296-303. 6645121 http://hmdb.ca/system/metabolites/msds/000/001/130/original/HMDB01262.pdf?1358461768 Maltodextrin phosphorylase P00490 PHSM_ECOLI malP http://ecmdb.ca/proteins/P00490.xml 4-alpha-glucanotransferase P15977 MALQ_ECOLI malQ http://ecmdb.ca/proteins/P15977.xml Maltodextrin glucosidase P21517 MALZ_ECOLI malZ http://ecmdb.ca/proteins/P21517.xml Maltose/maltodextrin import ATP-binding protein MalK P68187 MALK_ECOLI malK http://ecmdb.ca/proteins/P68187.xml Maltose transport system permease protein malF P02916 MALF_ECOLI malF http://ecmdb.ca/proteins/P02916.xml Maltose transport system permease protein malG P68183 MALG_ECOLI malG http://ecmdb.ca/proteins/P68183.xml Maltose-binding periplasmic protein P0AEX9 MALE_ECOLI malE http://ecmdb.ca/proteins/P0AEX9.xml Maltose/maltodextrin import ATP-binding protein MalK P68187 MALK_ECOLI malK http://ecmdb.ca/proteins/P68187.xml Maltose transport system permease protein malF P02916 MALF_ECOLI malF http://ecmdb.ca/proteins/P02916.xml Maltose transport system permease protein malG P68183 MALG_ECOLI malG http://ecmdb.ca/proteins/P68183.xml Maltose-binding periplasmic protein P0AEX9 MALE_ECOLI malE http://ecmdb.ca/proteins/P0AEX9.xml Maltoporin P02943 LAMB_ECOLI lamB http://ecmdb.ca/proteins/P02943.xml Adenosine triphosphate + Water + Maltotriose > ADP + Hydrogen ion + Maltotriose + Phosphate TRANS-RXN0-503 Adenosine triphosphate + Water + Maltotriose > ADP + Hydrogen ion + Maltotriose + Phosphate TRANS-RXN0-503 Water + Maltotriose > D-Glucose + D-Maltose RXN0-5183 Water + Maltotetraose > D-Glucose + Maltotriose D-Maltose + Maltotriose > D-Glucose + Maltotetraose Maltotriose + D-Maltose <> Maltotetraose + b-D-Glucose AMYLOMALT-RXN Maltotetraose + Phosphate <> Maltotriose + Glucose 1-phosphate RXN0-5182 Maltotriose + Water > D-Maltose + D-Glucose RXN0-5183 Maltotriose + Adenosine triphosphate + Water > ADP + Phosphate + Maltotriose + Hydrogen ion TRANS-RXN0-503 Maltotriose + Adenosine triphosphate + Water > ADP + Phosphate + Maltotriose + Hydrogen ion TRANS-RXN0-503 Maltotetraose + Phosphate > Maltotriose + Alpha-D-glucose 1-phosphate PW_R003522 Maltotriose + Adenosine triphosphate + Water > Adenosine diphosphate + Phosphate + Hydrogen ion + Maltotriose + ADP PW_RCT000155 Maltotriose + Adenosine triphosphate + Water > Adenosine diphosphate + Phosphate + Hydrogen ion + Maltotriose + ADP PW_RCT000155