2.02012-05-31 09:57:17 -06002015-09-13 12:56:06 -0600ECMDB00098M2MDB000037D-XyloseXylose or wood sugar is an aldopentose - a monosaccharide containing five carbon atoms and an aldehyde functional group. It has chemical formula C5H10O5 and is 40% as sweet as sucrose. Xylose is found in the embryos of most edible plants. The polysaccharide xylan, which is closely associated with cellulose, consists practically entirely of d-xylose. Corncobs, cottonseed hulls, pecan shells, and straw contain considerable amounts of this sugar. Xylose is the first sugar added to serine or threonine residues during proteoglycan type O-glycosylation. Therefore xylose is involved in the biosythetic pathways of most anionic polysaccharides such as heparan sulphate and chondroitin sulphate.α-D-xylosea-D-XyloseAlpha-D-XyloseD-(+)-XyloseD-Xylo-pentoseD-XyloseWood sugarXylo-pfanXylomedXyloseXylosideα-D-XyloseC5H10O5150.1299150.05282343(3R,4S,5R)-oxane-2,3,4,5-tetrold-xylose58-86-6O[C@@H]1COC(O)[C@H](O)[C@H]1OInChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1SRBFZHDQGSBBOR-IOVATXLUSA-NSolidCytosolExtra-organismPeriplasmlogp-2.57logs0.91solubility1.22e+03 g/lmelting_point90.5 oClogp-2.3pka_strongest_acidic11.31pka_strongest_basic-3.5iupac(3R,4S,5R)-oxane-2,3,4,5-tetrolaverage_mass150.1299mono_mass150.05282343smilesO[C@@H]1COC(O)[C@H](O)[C@H]1OformulaC5H10O5inchiInChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1inchikeySRBFZHDQGSBBOR-IOVATXLUSA-Npolar_surface_area90.15refractivity29.96polarizability13.43rotatable_bond_count0acceptor_count5donor_count4physiological_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-phosphatePW000941ec00500MetabolicAmino sugar and nucleotide sugar metabolismec00520Pentose and glucuronate interconversionsec00040ABC transportersec02010Specdb::CMs25082Specdb::CMs37293Specdb::CMs102604Specdb::CMs102605Specdb::CMs102606Specdb::CMs102607Specdb::CMs158325Specdb::CMs1049954Specdb::CMs1049955Specdb::CMs1049957Specdb::CMs1049959Specdb::CMs1049961Specdb::CMs1049963Specdb::CMs1049964Specdb::CMs1049966Specdb::CMs1049968Specdb::CMs1049970Specdb::CMs1049972Specdb::CMs1049974Specdb::CMs1049976Specdb::CMs1049977Specdb::CMs1049979Specdb::CMs1049981Specdb::CMs1049983Specdb::CMs1049985Specdb::NmrOneD1083Specdb::NmrOneD1145Specdb::NmrOneD142170Specdb::NmrOneD142171Specdb::NmrOneD142172Specdb::NmrOneD142173Specdb::NmrOneD142174Specdb::NmrOneD142175Specdb::NmrOneD142176Specdb::NmrOneD142177Specdb::NmrOneD142178Specdb::NmrOneD142179Specdb::NmrOneD142180Specdb::NmrOneD142181Specdb::NmrOneD142182Specdb::NmrOneD142183Specdb::NmrOneD142184Specdb::NmrOneD142185Specdb::NmrOneD142186Specdb::NmrOneD142187Specdb::NmrOneD142188Specdb::NmrOneD142189Specdb::MsMs153Specdb::MsMs154Specdb::MsMs155Specdb::MsMs321589Specdb::MsMs321590Specdb::MsMs321591Specdb::MsMs369244Specdb::MsMs369245Specdb::MsMs369246Specdb::MsMs2227272Specdb::MsMs2227432Specdb::MsMs2229628Specdb::MsMs2229866Specdb::MsMs2234459Specdb::MsMs2234480Specdb::MsMs2677755Specdb::MsMs2677756Specdb::MsMs2677757Specdb::MsMs3030968Specdb::MsMs3030969Specdb::MsMs3030970Specdb::NmrTwoD956Specdb::NmrTwoD1141HMDB00098135191119104C0018115936XYLOSEXyloseKeseler, 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). 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Proceedings of the Conference of the Australian Society of Sugar Cane Technologists (1999), 21st 394-400. http://hmdb.ca/system/metabolites/msds/000/000/068/original/HMDB00098.pdf?1358894054Xylose isomeraseP00944XYLA_ECOLIxylAhttp://ecmdb.ca/proteins/P00944.xmlXylose import ATP-binding protein XylGP37388XYLG_ECOLIxylGhttp://ecmdb.ca/proteins/P37388.xmlPutative beta-xylosidaseP77713YAGH_ECOLIyagHhttp://ecmdb.ca/proteins/P77713.xmlXylose transport system permease protein xylHP0AGI4XYLH_ECOLIxylHhttp://ecmdb.ca/proteins/P0AGI4.xmlD-xylose-binding periplasmic proteinP37387XYLF_ECOLIxylFhttp://ecmdb.ca/proteins/P37387.xmlXylose import ATP-binding protein XylGP37388XYLG_ECOLIxylGhttp://ecmdb.ca/proteins/P37388.xmlD-xylose-proton symporterP0AGF4XYLE_ECOLIxylEhttp://ecmdb.ca/proteins/P0AGF4.xmlXylose transport system permease protein xylHP0AGI4XYLH_ECOLIxylHhttp://ecmdb.ca/proteins/P0AGI4.xmlD-xylose-binding periplasmic proteinP37387XYLF_ECOLIxylFhttp://ecmdb.ca/proteins/P37387.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlAdenosine triphosphate + Water + D-Xylose > ADP + Hydrogen ion + Phosphate + D-XyloseABC-33-RXNAdenosine triphosphate + Water + D-Xylose > ADP + Hydrogen ion + Phosphate + D-XyloseABC-33-RXND-Xylose <> D-XyluloseR01432D-Xylose + 1,4-beta-D-Xylan <> 1,4-beta-D-Xylan + WaterR01433Adenosine triphosphate + D-Xylose + Water > ADP + Phosphate + D-Xylose + Hydrogen ionABC-33-RXNAdenosine triphosphate + D-Xylose + Water > ADP + Phosphate + D-Xylose + Hydrogen ionABC-33-RXNisoprimeverose + Water b-D-Glucose + D-XyloseRXN-12402xylan + Water D-XyloseRXN0-5001D-Xylose > D-Xylulose