2.02012-05-31 14:04:55 -06002015-06-04 18:21:29 -0600ECMDB04097M2MDB000608L-LyxosePectin is a heterosaccharide derived from the cell wall of plants. Pectins vary in their chain lengths, complexity and the order of each of the monosaccharide units. The characteristic structure of pectin is a linear chain of alpha(1-4)linked D-galacturonic acid that forms the pectin-backbone, a homogalacturonan.(+)-Xylose2,3,4,5-TetrahydroxypentanalD-LyxoseDL-XyloseL(+)-XyloseL-LyxoseLyxosePectinPectin sugarPectinosePentoseTrobicinC6H10O7194.1394194.042652674(2S,3R,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acidβ-D-galactopyranuronic acid9000-69-5O[C@@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)C(O)=OInChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2+,3+,4-,6+/m0/s1AEMOLEFTQBMNLQ-DTEWXJGMSA-NSolidCytosolExtra-organismPeriplasmlogp-2.30logs0.18solubility2.95e+02 g/lmelting_point116 - 121logp-2.6pka_strongest_acidic3.21pka_strongest_basic-3.7iupac(2S,3R,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acidaverage_mass194.1394mono_mass194.042652674smilesO[C@@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)C(O)=OformulaC6H10O7inchiInChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2+,3+,4-,6+/m0/s1inchikeyAEMOLEFTQBMNLQ-DTEWXJGMSA-Npolar_surface_area127.45refractivity35.79polarizability16.37rotatable_bond_count1acceptor_count7donor_count5physiological_charge-1formal_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-phosphatePW000941ec00500MetabolicAmino sugar and nucleotide sugar metabolismec00520Pentose and glucuronate interconversionsec00040Specdb::CMs2606Specdb::CMs38590Specdb::CMs137757Specdb::CMs145491Specdb::NmrOneD21602Specdb::NmrOneD21603Specdb::NmrOneD21604Specdb::NmrOneD21605Specdb::NmrOneD21606Specdb::NmrOneD21607Specdb::NmrOneD21608Specdb::NmrOneD21609Specdb::NmrOneD21610Specdb::NmrOneD21611Specdb::NmrOneD21612Specdb::NmrOneD21613Specdb::NmrOneD21614Specdb::NmrOneD21615Specdb::NmrOneD21616Specdb::NmrOneD21617Specdb::NmrOneD21618Specdb::NmrOneD21619Specdb::NmrOneD21620Specdb::NmrOneD21621Specdb::MsMs2277Specdb::MsMs2278Specdb::MsMs2279Specdb::MsMs178524Specdb::MsMs178525Specdb::MsMs178526Specdb::MsMs180843Specdb::MsMs180844Specdb::MsMs180845Specdb::MsMs2290176Specdb::MsMs2290177Specdb::MsMs2290178Specdb::MsMs2649396Specdb::MsMs2649397Specdb::MsMs2649398Specdb::NmrTwoD1097Specdb::NmrTwoD1894HMDB03402390200C01508PECTINGTRL-LyxoseKanehisa, 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-D114.22080510Winder, 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):910-4.19212411Andoh A, Bamba T, Sasaki M: Physiological and anti-inflammatory roles of dietary fiber and butyrate in intestinal functions. JPEN J Parenter Enteral Nutr. 1999 Sep-Oct;23(5 Suppl):S70-3.10483900Fleming SE, Marthinsen D, Kuhnlein H: Colonic function and fermentation in men consuming high fiber diets. J Nutr. 1983 Dec;113(12):2535-44.6317826Lewinska D, Rosinski S, Piatkiewicz W: A new pectin-based material for selective LDL-cholesterol removal. Artif Organs. 1994 Mar;18(3):217-22.8185488Kelsay JL, Goering HK, Behall KM, Prather ES: Effect of fiber from fruits and vegetables on metabolic responses of human subjects: fiber intakes, fecal excretions, and apparent digestibilities. Am J Clin Nutr. 1981 Sep;34(9):1849-52.6269418Baig MM, Cerda JJ: Pectin: its interaction with serum lipoproteins. Am J Clin Nutr. 1981 Jan;34(1):50-3.7446458Lairon D, Lafont H, Vigne JL, Nalbone G, Leonardi J, Hauton JC: Effects of dietary fibers and cholestyramine on the activity of pancreatic lipase in vitro. Am J Clin Nutr. 1985 Oct;42(4):629-38.2996326Miettinen TA, Tarpila S: Effect of pectin on serum cholesterol, fecal bile acids and biliary lipids in normolipidemic and hyperlipidemic individuals. Clin Chim Acta. 1977 Sep 1;79(2):471-7.890983Bosaeus I, Carlsson NG, Sandberg AS, Andersson H: Effect of wheat bran and pectin on bile acid and cholesterol excretion in ileostomy patients. Hum Nutr Clin Nutr. 1986 Nov;40(6):429-40.3025137Fan TY, Feng QQ, Jia CR, Fan Q, Li CA, Bai XL: Protective effect of Weikang decoction and partial ingredients on model rat with gastric mucosa ulcer. World J Gastroenterol. 2005 Feb 28;11(8):1204-9.15754406Levy MC, Edwards-Levy F: Coating alginate beads with cross-linked biopolymers: a novel method based on a transacylation reaction. J Microencapsul. 1996 Mar-Apr;13(2):169-83.8999122Veldman FJ, Nair CH, Vorster HH, Vermaak WJ, Jerling JC, Oosthuizen W, Venter CS: Possible mechanisms through which dietary pectin influences fibrin network architecture in hypercholesterolaemic subjects. Thromb Res. 1999 Mar 15;93(6):253-64.10093966Gu, Qu-Ming; Nickol, Robert G.; Cheng, H. N. Enzyme-catalyzed modification of pectin. Polymer Preprints (American Chemical Society, Division of Polymer Chemistry) (2003), 44(2), 608-609.L-rhamnose isomeraseP32170RHAA_ECOLIrhaAhttp://ecmdb.ca/proteins/P32170.xmlPutative acyl-CoA thioester hydrolase ybhCP46130YBHC_ECOLIybhChttp://ecmdb.ca/proteins/P46130.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlL-rhamnose-proton symporterP27125RHAT_ECOLIrhaThttp://ecmdb.ca/proteins/P27125.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlL-Lyxose > L-Threo-2-pentuloseL-Lyxose + Water <> Methanol + Pectic acidR02362