2.0 2012-08-15 08:51:32 -0600 2015-09-17 15:41:21 -0600 ECMDB21651 M2MDB002045 Dextrin Dextrins are a group of low-molecular-weight carbohydrates produced by the hydrolysis of starch or glycogen. Dextrins are mixtures of polymers of D-glucose units linked by -(1_4) or -(1_6) glycosidic bonds. The cyclical dextrins are known as cyclodextrins. They are formed by enzymatic degradation of starch by certain bacteria, for example, Bacillus macerans. Cyclodextrins have toroidal structures formed by 6-8 glucose residues. (Wikipedia) In E. coli metabolism, the enzyme alpha-amylase (EC 3.2.1.1) catalyzes the breakdown of glycogen into dextrin. (KEGG) British gum Caloreen Corn dextrin Crystal gum Dextrid Dextrina Bianca Dextrine Dextrins Fortodex C18H32O16 504.4371 504.169034976 2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol amylose 9004-53-9 OC[C@H]1OC(O[C@H]2[C@H](O)[C@@H](O)C(O[C@H]3[C@H](O)[C@@H](O)[C@@H](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-MRCIVHHJSA-N Solid 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 2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{[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]1OC(O[C@H]2[C@H](O)[C@@H](O)C(O[C@H]3[C@H](O)[C@@H](O)[C@@H](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-MRCIVHHJSA-N ChemAxon polar_surface_area 268.68 ChemAxon refractivity 100.75 ChemAxon polarizability 47.51 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 Specdb::CMs 15574 Specdb::CMs 46101 Specdb::CMs 169638 Specdb::CMs 169641 Specdb::CMs 169643 Specdb::CMs 169645 Specdb::CMs 169647 Specdb::CMs 169649 Specdb::CMs 169651 Specdb::CMs 169653 Specdb::CMs 169655 Specdb::CMs 169657 Specdb::CMs 169659 Specdb::CMs 169661 Specdb::CMs 169663 Specdb::CMs 169665 Specdb::CMs 169667 Specdb::CMs 169669 Specdb::CMs 169671 Specdb::CMs 169673 Specdb::CMs 169675 Specdb::CMs 169677 Specdb::CMs 169679 Specdb::CMs 169681 Specdb::CMs 169684 Specdb::NmrOneD 4059 Specdb::NmrOneD 29582 Specdb::NmrOneD 29583 Specdb::NmrOneD 29584 Specdb::NmrOneD 29585 Specdb::NmrOneD 29586 Specdb::NmrOneD 29587 Specdb::NmrOneD 29588 Specdb::NmrOneD 29589 Specdb::NmrOneD 29590 Specdb::NmrOneD 29591 Specdb::NmrOneD 29592 Specdb::NmrOneD 29593 Specdb::NmrOneD 29594 Specdb::NmrOneD 29595 Specdb::NmrOneD 29596 Specdb::NmrOneD 29597 Specdb::NmrOneD 29598 Specdb::NmrOneD 29599 Specdb::NmrOneD 29600 Specdb::NmrOneD 29601 Specdb::MsMs 9344 Specdb::MsMs 9345 Specdb::MsMs 9346 Specdb::MsMs 9956 Specdb::MsMs 9957 Specdb::MsMs 9958 Specdb::MsMs 10349 Specdb::MsMs 10350 Specdb::MsMs 10351 Specdb::MsMs 16016 Specdb::MsMs 16017 Specdb::MsMs 16018 Specdb::MsMs 16628 Specdb::MsMs 16629 Specdb::MsMs 16630 Specdb::MsMs 17021 Specdb::MsMs 17022 Specdb::MsMs 17023 Specdb::MsMs 2809979 Specdb::MsMs 2809980 Specdb::MsMs 2809981 Specdb::MsMs 2899665 Specdb::MsMs 2899666 Specdb::MsMs 2899667 HMDB06857 62698 848 C00721 Dextrin Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC. http://hmdb.ca/system/metabolites/msds/000/005/982/original/HMDB06857.pdf?1358894077 Glycogen phosphorylase P0AC86 PHSG_ECOLI glgP http://ecmdb.ca/proteins/P0AC86.xml Alpha-amylase P25718 AMY1_ECOLI malS http://ecmdb.ca/proteins/P25718.xml Cytoplasmic alpha-amylase P26612 AMY2_ECOLI amyA http://ecmdb.ca/proteins/P26612.xml Glycogen debranching enzyme P15067 GLGX_ECOLI glgX http://ecmdb.ca/proteins/P15067.xml Starch + Water <> Dextrin + Starch R02108 Glycogen + Phosphate > Alpha-D-glucose 1-phosphate + Dextrin + Dextrin PW_R003520 Dextrin + Water + Dextrin > debranched limit dextrin + Maltotetraose PW_R003521