2.0 2012-05-31 13:49:19 -0600 2015-09-13 15:15:22 -0600 ECMDB01296 M2MDB000327 Maltotetraose Maltotetraose is a member of the chemical class known as Tetrahexoses. These are tetrasaccharides containing four hexose carbohydrates. Maltotetraose is invovled in Glycerol degradation. r 15;80(8):2939-48.) a-1,4-Tetraglucose Alpha-1,4-Tetraglucose Amylotetraose Maltotetraose Maltotetraose (6CI,8CI) O-a-D-Glucopyranosyl-(1-4)-O-a-D-glucopyranosyl-(1-4)-O-a-D-glucopyranosyl-(1-4)-D-glucose O-a-D-Glucopyranosyl-(1-4)-O-a-D-glucopyranosyl-(1-4)-O-a-D-glucopyranosyl-(1-4)-D-glucose (9ci) O-a-D-Glucopyranosyl-(1->4)-O(4XI)-a-D-xylo-hexopyranosyl-(1->4)-O-a-D-glucopyranosyl-(1->4)-D-glucose O-a-D-Glucopyranosyl-(1.4)-O-a-D-glucopyranosyl-(1.4)-O-a-D-glucopyranosyl-(1.4)-D-glucose O-a-delta-Glucopyranosyl-(1-4)-O-a-delta-glucopyranosyl-(1-4)-O-a-delta-glucopyranosyl-(1-4)-delta-glucose O-a-delta-Glucopyranosyl-(1->4)-O(4XI)-a-delta-xylo-hexopyranosyl-(1->4)-O-a-delta-glucopyranosyl-(1->4)-delta-glucose O-a-delta-Glucopyranosyl-(1.4)-O-a-delta-glucopyranosyl-(1.4)-O-a-delta-glucopyranosyl-(1.4)-delta-glucose O-a-δ-Glucopyranosyl-(1-4)-O-a-δ-glucopyranosyl-(1-4)-O-a-δ-glucopyranosyl-(1-4)-δ-glucose O-a-δ-Glucopyranosyl-(1->4)-O(4xi)-a-δ-xylo-hexopyranosyl-(1->4)-O-a-δ-glucopyranosyl-(1->4)-δ-glucose O-a-δ-Glucopyranosyl-(1.4)-O-a-δ-glucopyranosyl-(1.4)-O-a-δ-glucopyranosyl-(1.4)-δ-glucose O-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-D-Glucose O-alpha-D-Glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-D-Glucose (9CI) O-alpha-D-Glucopyranosyl-(1->4)-O(4xi)-alpha-D-xylo-hexopyranosyl-(1->4)-O-alpha-D-glucopyranosyl-(1->4)-D-glucose O-alpha-D-Glucopyranosyl-(1.4)-O-alpha-D-glucopyranosyl-(1.4)-O-alpha-D-glucopyranosyl-(1.4)-D-glucose O-alpha-delta-glucopyranosyl-(1-4)-O-alpha-delta-glucopyranosyl-(1-4)-O-alpha-delta-glucopyranosyl-(1-4)-delta-Glucose O-alpha-delta-glucopyranosyl-(1->4)-O(4xi)-alpha-delta-xylo-hexopyranosyl-(1->4)-O-alpha-delta-glucopyranosyl-(1->4)-delta-glucose O-alpha-delta-Glucopyranosyl-(1.4)-O-alpha-delta-glucopyranosyl-(1.4)-O-alpha-delta-glucopyranosyl-(1.4)-delta-glucose O-α-D-Glucopyranosyl-(1-4)-O-α-D-glucopyranosyl-(1-4)-O-α-D-glucopyranosyl-(1-4)-D-glucose O-α-D-Glucopyranosyl-(1-4)-O-α-D-glucopyranosyl-(1-4)-O-α-D-glucopyranosyl-(1-4)-D-glucose (9ci) O-α-D-Glucopyranosyl-(1->4)-O(4XI)-α-D-xylo-hexopyranosyl-(1->4)-O-α-D-glucopyranosyl-(1->4)-D-glucose O-α-D-Glucopyranosyl-(1.4)-O-α-D-glucopyranosyl-(1.4)-O-α-D-glucopyranosyl-(1.4)-D-glucose O-α-δ-Glucopyranosyl-(1-4)-O-α-δ-glucopyranosyl-(1-4)-O-α-δ-glucopyranosyl-(1-4)-δ-glucose O-α-δ-Glucopyranosyl-(1->4)-O(4XI)-α-δ-xylo-hexopyranosyl-(1->4)-O-α-δ-glucopyranosyl-(1->4)-δ-glucose O-α-δ-Glucopyranosyl-(1.4)-O-α-δ-glucopyranosyl-(1.4)-O-α-δ-glucopyranosyl-(1.4)-δ-glucose α-1,4-Tetraglucose C24H42O21 666.5777 666.221858406 (3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol (3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol 34612-38-9 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@@H](O[C@H]4[C@H](O)[C@@H](O)C(O)O[C@@H]4CO)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C24H42O21/c25-1-5-9(29)10(30)15(35)22(40-5)44-19-7(3-27)42-24(17(37)12(19)32)45-20-8(4-28)41-23(16(36)13(20)33)43-18-6(2-26)39-21(38)14(34)11(18)31/h5-38H,1-4H2/t5-,6-,7-,8-,9-,10+,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21?,22-,23-,24-/m1/s1 LUEWUZLMQUOBSB-AYQJAVFRSA-N Solid Cytosol Extra-organism Periplasm logp -2.69 ALOGPS logs -0.28 ALOGPS solubility 3.50e+02 g/l ALOGPS logp -8.2 ChemAxon pka_strongest_acidic 11.19 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol ChemAxon average_mass 666.5777 ChemAxon mono_mass 666.221858406 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@@H](O[C@H]4[C@H](O)[C@@H](O)C(O)O[C@@H]4CO)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C24H42O21 ChemAxon inchi InChI=1S/C24H42O21/c25-1-5-9(29)10(30)15(35)22(40-5)44-19-7(3-27)42-24(17(37)12(19)32)45-20-8(4-28)41-23(16(36)13(20)33)43-18-6(2-26)39-21(38)14(34)11(18)31/h5-38H,1-4H2/t5-,6-,7-,8-,9-,10+,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21?,22-,23-,24-/m1/s1 ChemAxon inchikey LUEWUZLMQUOBSB-AYQJAVFRSA-N ChemAxon polar_surface_area 347.83 ChemAxon refractivity 133.16 ChemAxon polarizability 62.12 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 21 ChemAxon donor_count 14 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 glycogen degradation I GLYCOCAT-PWY Specdb::CMs 24917 Specdb::CMs 686649 Specdb::CMs 686650 Specdb::CMs 686651 Specdb::CMs 686652 Specdb::CMs 686653 Specdb::CMs 686654 Specdb::CMs 686655 Specdb::CMs 686656 Specdb::CMs 686657 Specdb::CMs 686658 Specdb::CMs 686659 Specdb::CMs 686660 Specdb::CMs 686661 Specdb::CMs 686662 Specdb::CMs 686663 Specdb::CMs 686664 Specdb::CMs 686665 Specdb::CMs 686666 Specdb::CMs 686667 Specdb::CMs 686668 Specdb::CMs 686669 Specdb::CMs 686670 Specdb::CMs 686671 Specdb::CMs 686672 Specdb::NmrOneD 1678 Specdb::NmrOneD 147210 Specdb::NmrOneD 147211 Specdb::NmrOneD 147212 Specdb::NmrOneD 147213 Specdb::NmrOneD 147214 Specdb::NmrOneD 147215 Specdb::NmrOneD 147216 Specdb::NmrOneD 147217 Specdb::NmrOneD 147218 Specdb::NmrOneD 147219 Specdb::NmrOneD 147220 Specdb::NmrOneD 147221 Specdb::NmrOneD 147222 Specdb::NmrOneD 147223 Specdb::NmrOneD 147224 Specdb::NmrOneD 147225 Specdb::NmrOneD 147226 Specdb::NmrOneD 147227 Specdb::NmrOneD 147228 Specdb::NmrOneD 147229 Specdb::MsMs 1507 Specdb::MsMs 1508 Specdb::MsMs 1509 Specdb::MsMs 321205 Specdb::MsMs 321206 Specdb::MsMs 321207 Specdb::MsMs 368758 Specdb::MsMs 368759 Specdb::MsMs 368760 Specdb::MsMs 2279977 Specdb::MsMs 2279978 Specdb::MsMs 2279979 Specdb::MsMs 3089269 Specdb::MsMs 3089270 Specdb::MsMs 3089271 Specdb::NmrTwoD 1619 HMDB01296 439639 388711 C02052 MALTOTETRAOSE 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 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 Dewit O, Dibba B, Prentice A: Breast-milk amylase activity in English and Gambian mothers: effects of prolonged lactation, maternal parity, and individual variations. Pediatr Res. 1990 Nov;28(5):502-6. 1701531 An Y, Young SP, Kishnani PS, Millington DS, Amalfitano A, Corz D, Chen YT: Glucose tetrasaccharide as a biomarker for monitoring the therapeutic response to enzyme replacement therapy for Pompe disease. Mol Genet Metab. 2005 Aug;85(4):247-54. 15886040 Kuriyama M, Hiwatari R, Osame M, Igata A: Leucocyte alpha-1,4- and alpha-1,6-glucosidase activities towards oligosaccharides in late onset glycogenosis type II. Tohoku J Exp Med. 1990 Aug;161(4):343-51. 2256108 Whitlow KJ, Gochman N, Forrester RL, Wataji LJ: Maltotetraose as a substrate for enzyme-coupled assay of amylase activity in serum and urine. Clin Chem. 1979 Mar;25(3):481-3. 95558 Zhu, Ming. Production of maltotetraose. Wuxi Qinggong Daxue Xuebao (1999), 18(2), 7-12. http://hmdb.ca/system/metabolites/msds/000/001/159/original/HMDB01296.pdf?1358462613 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 Glycogen debranching enzyme P15067 GLGX_ECOLI glgX http://ecmdb.ca/proteins/P15067.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 + Maltotetraose > ADP + Hydrogen ion + Maltotetraose + Phosphate TRANS-RXN0-504 Adenosine triphosphate + Water + Maltotetraose > ADP + Hydrogen ion + Maltotetraose + Phosphate TRANS-RXN0-504 Water + Maltotetraose > D-Glucose + Maltotriose Water + Maltopentaose > D-Glucose + Maltotetraose D-Maltose + Maltotriose > D-Glucose + Maltotetraose D-Maltose + Maltotetraose > D-Glucose + Maltopentaose Maltopentaose + Phosphate <> Glucose 1-phosphate + Maltotetraose Maltotriose + D-Maltose <> Maltotetraose + b-D-Glucose AMYLOMALT-RXN a limit dextrin + Water > a debranched limit dextrin + Maltotetraose RXN0-5146 Maltotetraose + Phosphate <> Maltotriose + Glucose 1-phosphate RXN0-5182 Maltotetraose + Adenosine triphosphate + Water > ADP + Maltotetraose + Phosphate + Hydrogen ion TRANS-RXN0-504 Maltotetraose + Adenosine triphosphate + Water > ADP + Maltotetraose + Phosphate + Hydrogen ion TRANS-RXN0-504 Maltotetraose + Phosphate > Maltotriose + Alpha-D-glucose 1-phosphate PW_R003522 Dextrin + Water + Dextrin > debranched limit dextrin + Maltotetraose PW_R003521 Maltotetraose + Adenosine triphosphate + Water > Maltotetraose + Phosphate + Hydrogen ion + Adenosine diphosphate + ADP PW_RCT000154 Maltotetraose + Adenosine triphosphate + Water > Maltotetraose + Phosphate + Hydrogen ion + Adenosine diphosphate + ADP PW_RCT000154