2.0 2012-05-31 10:22:31 -0600 2015-09-13 12:56:06 -0600 ECMDB00163 M2MDB000065 D-Maltose Maltose, or malt sugar, is a disaccharide formed from two units of glucose joined with an alpha (1->4) linkage. It is the second member of an important biochemical series of glucose chains. The addition of another glucose unit yields maltotriose, Further additions will produce dextrins, also called maltodextrins, and eventually starch. Maltose can be broken down into two glucose molecules by hydrolysis in living organisms. (PMID: 14522745) 1-a-D-Glucopyranosyl-4-a-D-glucopyranose 1-a-delta-Glucopyranosyl-4-a-delta-glucopyranose 1-a-δ-Glucopyranosyl-4-a-δ-glucopyranose 1-alpha-D-Glucopyranosyl-4-alpha-D-glucopyranose 1-alpha-delta-Glucopyranosyl-4-alpha-delta-glucopyranose 1-α-D-Glucopyranosyl-4-α-D-glucopyranose 1-α-δ-Glucopyranosyl-4-α-δ-glucopyranose 4-(a-D-glucopyranosido)-a-Glucopyranose 4-(a-D-glucosido)-D-Glucose 4-(a-delta-glucopyranosido)-a-Glucopyranose 4-(a-delta-glucosido)-delta-Glucose 4-(a-δ-glucopyranosido)-a-Glucopyranose 4-(a-δ-glucosido)-δ-Glucose 4-(alpha-D-Glucopyranosido)-alpha-glucopyranose 4-(alpha-D-Glucosido)-D-glucose 4-(alpha-delta-Glucopyranosido)-alpha-glucopyranose 4-(alpha-delta-Glucosido)-delta-glucose 4-(α-D-glucopyranosido)-α-Glucopyranose 4-(α-D-glucosido)-D-Glucose 4-(α-δ-glucopyranosido)-α-Glucopyranose 4-(α-δ-glucosido)-δ-Glucose 4-O-a-D-Glucopyranosyl-D-glucopyranose 4-O-a-D-Glucopyranosyl-D-glucose 4-O-a-delta-Glucopyranosyl-delta-glucopyranose 4-O-a-delta-Glucopyranosyl-delta-glucose 4-O-a-δ-Glucopyranosyl-δ-glucopyranose 4-O-a-δ-Glucopyranosyl-δ-glucose 4-O-alpha-D-Glucopyranosyl-D-glucopyranose 4-O-alpha-D-Glucopyranosyl-D-glucose 4-O-alpha-delta-Glucopyranosyl-delta-glucopyranose 4-O-alpha-delta-Glucopyranosyl-delta-glucose 4-O-α-D-Glucopyranosyl-D-glucopyranose 4-O-α-D-Glucopyranosyl-D-glucose 4-O-α-δ-Glucopyranosyl-δ-glucopyranose 4-O-α-δ-Glucopyranosyl-δ-glucose a-D-GLCP-(1->4)-D-GLCP a-D-Glucopyranosyl-(1->4)-D-glucopyranose a-D-Glucopyranosyl-(1->4)-D-glucose a-delta-GLCP-(1->4)-delta-GLCP a-delta-Glucopyranosyl-(1->4)-delta-glucopyranose a-delta-Glucopyranosyl-(1->4)-delta-glucose a-Malt sugar a-δ-GLCP-(1->4)-δ-GLCP a-δ-Glucopyranosyl-(1->4)-δ-glucopyranose a-δ-Glucopyranosyl-(1->4)-δ-glucose Advantose 100 Alpha-D-Glcp-(1->4)-D-Glcp Alpha-D-Glucopyranosyl-(1->4)-D-glucopyranose Alpha-D-Glucopyranosyl-(1->4)-D-glucose Alpha-delta-Glcp-(1->4)-delta-Glcp Alpha-delta-Glucopyranosyl-(1->4)-delta-glucopyranose Alpha-delta-Glucopyranosyl-(1->4)-delta-glucose Alpha-Malt sugar Cextromaltose D-(+)-Maltose D-Maltose Delta-(+)-Maltose Delta-Maltose Finetose Finetose F Madoros Madoros (TN) Malt sugar Maltobiose Maltodiose Maltos Maltose Maltose HH Maltose HHH Maltose solution Malzzucker Martos-10 Sunmalt Sunmalt S α-D-GLCP-(1->4)-D-GLCP α-D-Glucopyranosyl-(1->4)-D-glucopyranose α-D-Glucopyranosyl-(1->4)-D-glucose α-Malt sugar α-δ-GLCP-(1->4)-δ-GLCP α-δ-Glucopyranosyl-(1->4)-δ-glucopyranose α-δ-Glucopyranosyl-(1->4)-δ-glucose δ-(+)-Maltose δ-Maltose C12H22O11 342.2965 342.116211546 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol 69-79-4 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-DKBJLJRDSA-N Solid Cytosol Extra-organism Periplasm logp -3.01 ALOGPS logs 0.23 ALOGPS solubility 5.86e+02 g/l ALOGPS melting_point 102-103 oC logp -4.7 ChemAxon pka_strongest_acidic 11.25 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-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-DKBJLJRDSA-N ChemAxon polar_surface_area 189.53 ChemAxon refractivity 68.34 ChemAxon polarizability 31.43 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 Bacterial chemotaxis ec02030 glycogen degradation I GLYCOCAT-PWY Specdb::CMs 15658 Specdb::CMs 37332 Specdb::CMs 148295 Specdb::CMs 148297 Specdb::CMs 148299 Specdb::CMs 148301 Specdb::CMs 148304 Specdb::CMs 148306 Specdb::CMs 148308 Specdb::CMs 148310 Specdb::CMs 148312 Specdb::CMs 173951 Specdb::CMs 279668 Specdb::CMs 1051769 Specdb::CMs 1051771 Specdb::CMs 1051773 Specdb::CMs 1051775 Specdb::CMs 1051777 Specdb::CMs 1051779 Specdb::CMs 1051781 Specdb::CMs 1051783 Specdb::CMs 1051785 Specdb::CMs 1051787 Specdb::CMs 1051789 Specdb::CMs 1051791 Specdb::NmrOneD 1125 Specdb::NmrOneD 1181 Specdb::NmrOneD 5932 Specdb::NmrOneD 5933 Specdb::NmrOneD 5934 Specdb::NmrOneD 5935 Specdb::NmrOneD 5936 Specdb::NmrOneD 5937 Specdb::NmrOneD 5938 Specdb::NmrOneD 5939 Specdb::NmrOneD 5940 Specdb::NmrOneD 5941 Specdb::NmrOneD 5942 Specdb::NmrOneD 5943 Specdb::NmrOneD 5944 Specdb::NmrOneD 5945 Specdb::NmrOneD 5946 Specdb::NmrOneD 5947 Specdb::NmrOneD 5948 Specdb::NmrOneD 5949 Specdb::NmrOneD 5950 Specdb::NmrOneD 5951 Specdb::NmrOneD 166525 Specdb::MsMs 257 Specdb::MsMs 258 Specdb::MsMs 259 Specdb::MsMs 300682 Specdb::MsMs 300683 Specdb::MsMs 300684 Specdb::MsMs 343009 Specdb::MsMs 343010 Specdb::MsMs 343011 Specdb::MsMs 2423731 Specdb::MsMs 2423732 Specdb::MsMs 2423733 Specdb::MsMs 2515392 Specdb::MsMs 2515393 Specdb::MsMs 2515394 Specdb::NmrTwoD 978 Specdb::NmrTwoD 1180 HMDB00163 439186 9166684 C00208 17306 MALTOSE Malt sugar Keseler, I. 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(2001), 99 pp. http://hmdb.ca/system/metabolites/msds/000/000/114/original/HMDB00163.pdf?1358461794 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml 4-alpha-glucanotransferase P15977 MALQ_ECOLI malQ http://ecmdb.ca/proteins/P15977.xml PTS system maltose- and glucose-specific EIICB component P19642 PTOCB_ECOLI malX http://ecmdb.ca/proteins/P19642.xml Maltodextrin glucosidase P21517 MALZ_ECOLI malZ http://ecmdb.ca/proteins/P21517.xml Alpha-glucosidase yihQ P32138 YIHQ_ECOLI yihQ http://ecmdb.ca/proteins/P32138.xml Maltose/maltodextrin import ATP-binding protein MalK P68187 MALK_ECOLI malK http://ecmdb.ca/proteins/P68187.xml Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml Maltose O-acetyltransferase P77791 MAA_ECOLI maa http://ecmdb.ca/proteins/P77791.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 Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml PTS system maltose- and glucose-specific EIICB component P19642 PTOCB_ECOLI malX http://ecmdb.ca/proteins/P19642.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 Phosphoenolpyruvic acid + D-Maltose > Maltose 6'-phosphate + Pyruvic acid Adenosine triphosphate + Water + D-Maltose > ADP + Hydrogen ion + D-Maltose + Phosphate ABC-16-RXN Adenosine triphosphate + Water + D-Maltose > ADP + Hydrogen ion + D-Maltose + Phosphate ABC-16-RXN Water + Maltotriose > D-Glucose + D-Maltose RXN0-5183 Acetyl-CoA + D-Maltose <> Acetyl-maltose + Coenzyme A MALTACETYLTRAN-RXN D-Maltose + Maltotriose > D-Glucose + Maltotetraose D-Maltose + Maltotetraose > D-Glucose + Maltopentaose D-Maltose + Maltohexaose > D-Glucose + Maltoheptaose D-Maltose + Maltopentaose > D-Glucose + Maltohexaose D-Maltose + Water <>2 alpha-D-Glucose R00028 Protein N(pi)-phospho-L-histidine + D-Maltose <> Protein histidine + Maltose 6'-phosphate R04111 1,4-alpha-D-glucan + D-Glucose <> D-Maltose R05196 Adenosine triphosphate + D-Maltose + Water > ADP + Phosphate + D-Maltose + Hydrogen ion ABC-16-RXN Adenosine triphosphate + D-Maltose + Water > ADP + Phosphate + D-Maltose + Hydrogen ion ABC-16-RXN Maltotriose + D-Maltose <> Maltotetraose + b-D-Glucose AMYLOMALT-RXN Maltotriose + Water > D-Maltose + D-Glucose RXN0-5183 Acetyl-CoA + D-Maltose > CoA + Acetyl-maltose Adenosine triphosphate + Water + D-Maltose > ADP + Inorganic phosphate + D-Maltose Adenosine triphosphate + Water + D-Maltose > ADP + Inorganic phosphate + D-Maltose ADP + Phosphate + 4 Hydrogen ion + Heme + Nickel(2+) + Iron chelate + Taurine + Molybdate + Magnesium + Fe3+ + Potassium + Polyamine + vitamin B12 + Sulfate + glycerol-3-phosphate + Phosphonate + D-Maltose <> Adenosine triphosphate +3 Hydrogen ion + Water R00086 RXN0-1061 D-Maltose + Adenosine triphosphate + Water > D-Maltose + Phosphate + Hydrogen ion + Adenosine diphosphate + ADP PW_RCT000156 D-Maltose + Adenosine triphosphate + Water > D-Maltose + Phosphate + Hydrogen ion + Adenosine diphosphate + ADP PW_RCT000156