2.02012-05-31 13:48:37 -06002015-09-13 12:56:10 -0600ECMDB01262M2MDB000315MaltotrioseMaltotriose 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)hexoseAmylotrioseD-(+)-MaltotrioseDelta-(+)-MaltotrioseMaltotrioseO-a-D-Glucopyranosyl-(1b94)-O-a-D-glucopyranosyl-(1b94)-O-a-D-glucoseO-a-delta-Glucopyranosyl-(1b94)-O-a-delta-glucopyranosyl-(1b94)-O-a-delta-glucoseO-a-δ-Glucopyranosyl-(1b94)-O-a-δ-glucopyranosyl-(1b94)-O-a-δ-glucoseO-alpha-D-Glucopyranosyl-(1beta94)-O-alpha-D-glucopyranosyl-(1beta94)-O-alpha-D-glucoseO-alpha-delta-Glucopyranosyl-(1beta94)-O-alpha-delta-glucopyranosyl-(1beta94)-O-alpha-delta-glucoseO-α-D-Glucopyranosyl-(1β94)-O-α-D-glucopyranosyl-(1β94)-O-α-D-glucoseO-α-δ-Glucopyranosyl-(1β94)-O-α-δ-glucopyranosyl-(1β94)-O-α-δ-glucoseδ-(+)-MaltotrioseC18H32O16504.4371504.169034976(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-triolmaltotriose1109-28-0OC[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]1OInChI=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/s1FYGDTMLNYKFZSV-DZOUCCHMSA-NSolidCytosolExtra-organismPeriplasmlogp-2.74logs0.04solubility5.54e+02 g/llogp-6.5pka_strongest_acidic11.22pka_strongest_basic-3.6iupac(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-triolaverage_mass504.4371mono_mass504.169034976smilesOC[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]1OformulaC18H32O16inchiInChI=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/s1inchikeyFYGDTMLNYKFZSV-DZOUCCHMSA-Npolar_surface_area268.68refractivity100.75polarizability46.65rotatable_bond_count7acceptor_count16donor_count11physiological_charge0formal_charge0Starch and sucrose metabolismThe 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-phosphatePW000941ec00500MetabolicPorphyrin and chlorophyll metabolismec00860glycogen degradation IGLYCOCAT-PWYSpecdb::CMs722Specdb::CMs723Specdb::CMs724Specdb::CMs725Specdb::CMs726Specdb::CMs727Specdb::CMs12583Specdb::CMs31916Specdb::CMs31917Specdb::CMs37997Specdb::CMs168767Specdb::CMs168769Specdb::CMs168771Specdb::CMs168774Specdb::CMs168776Specdb::CMs168778Specdb::CMs168780Specdb::CMs168782Specdb::CMs168784Specdb::CMs168786Specdb::CMs168789Specdb::CMs168791Specdb::CMs168793Specdb::CMs168795Specdb::CMs168798Specdb::NmrOneD1673Specdb::NmrOneD87632Specdb::NmrOneD87633Specdb::NmrOneD87634Specdb::NmrOneD87635Specdb::NmrOneD87636Specdb::NmrOneD87637Specdb::NmrOneD87638Specdb::NmrOneD87639Specdb::NmrOneD87640Specdb::NmrOneD87641Specdb::NmrOneD87642Specdb::NmrOneD87643Specdb::NmrOneD87644Specdb::NmrOneD87645Specdb::NmrOneD87646Specdb::NmrOneD87647Specdb::NmrOneD87648Specdb::NmrOneD87649Specdb::NmrOneD87650Specdb::NmrOneD87651Specdb::MsMs5167Specdb::MsMs5168Specdb::MsMs2226735Specdb::MsMs2231378Specdb::MsMs2232848Specdb::MsMs2233789Specdb::MsMs2235136Specdb::MsMs2255878Specdb::MsMs1494Specdb::MsMs1495Specdb::MsMs1496Specdb::MsMs2228010Specdb::MsMs2229052Specdb::MsMs2230382Specdb::MsMs334234Specdb::MsMs334235Specdb::MsMs334236Specdb::MsMs2891532Specdb::MsMs2891533Specdb::MsMs2891534Specdb::MsMs293710Specdb::MsMs293711Specdb::MsMs293712Specdb::MsMs2813576Specdb::MsMs2813577Specdb::NmrTwoD1614HMDB01262439586388669C0183527931MALTOTRIOSEKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Sreekumar 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):910-4.19212411Lingstrom 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):394-401.8242677Yuge 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):296-303.6645121http://hmdb.ca/system/metabolites/msds/000/001/130/original/HMDB01262.pdf?1358461768Maltodextrin phosphorylaseP00490PHSM_ECOLImalPhttp://ecmdb.ca/proteins/P00490.xml4-alpha-glucanotransferaseP15977MALQ_ECOLImalQhttp://ecmdb.ca/proteins/P15977.xmlMaltodextrin glucosidaseP21517MALZ_ECOLImalZhttp://ecmdb.ca/proteins/P21517.xmlMaltose/maltodextrin import ATP-binding protein MalKP68187MALK_ECOLImalKhttp://ecmdb.ca/proteins/P68187.xmlMaltose transport system permease protein malFP02916MALF_ECOLImalFhttp://ecmdb.ca/proteins/P02916.xmlMaltose transport system permease protein malGP68183MALG_ECOLImalGhttp://ecmdb.ca/proteins/P68183.xmlMaltose-binding periplasmic proteinP0AEX9MALE_ECOLImalEhttp://ecmdb.ca/proteins/P0AEX9.xmlMaltose/maltodextrin import ATP-binding protein MalKP68187MALK_ECOLImalKhttp://ecmdb.ca/proteins/P68187.xmlMaltose transport system permease protein malFP02916MALF_ECOLImalFhttp://ecmdb.ca/proteins/P02916.xmlMaltose transport system permease protein malGP68183MALG_ECOLImalGhttp://ecmdb.ca/proteins/P68183.xmlMaltose-binding periplasmic proteinP0AEX9MALE_ECOLImalEhttp://ecmdb.ca/proteins/P0AEX9.xmlMaltoporinP02943LAMB_ECOLIlamBhttp://ecmdb.ca/proteins/P02943.xmlAdenosine triphosphate + Water + Maltotriose > ADP + Hydrogen ion + Maltotriose + PhosphateTRANS-RXN0-503Adenosine triphosphate + Water + Maltotriose > ADP + Hydrogen ion + Maltotriose + PhosphateTRANS-RXN0-503Water + Maltotriose > D-Glucose + D-MaltoseRXN0-5183Water + Maltotetraose > D-Glucose + MaltotrioseD-Maltose + Maltotriose > D-Glucose + MaltotetraoseMaltotriose + D-Maltose <> Maltotetraose + b-D-GlucoseAMYLOMALT-RXNMaltotetraose + Phosphate <> Maltotriose + Glucose 1-phosphateRXN0-5182Maltotriose + Water > D-Maltose + D-GlucoseRXN0-5183Maltotriose + Adenosine triphosphate + Water > ADP + Phosphate + Maltotriose + Hydrogen ionTRANS-RXN0-503Maltotriose + Adenosine triphosphate + Water > ADP + Phosphate + Maltotriose + Hydrogen ionTRANS-RXN0-503Maltotetraose + Phosphate > Maltotriose + Alpha-D-glucose 1-phosphatePW_R003522Maltotriose + Adenosine triphosphate + Water > Adenosine diphosphate + Phosphate + Hydrogen ion + Maltotriose + ADPPW_RCT000155Maltotriose + Adenosine triphosphate + Water > Adenosine diphosphate + Phosphate + Hydrogen ion + Maltotriose + ADPPW_RCT000155