2.0 2012-05-31 09:57:17 -0600 2015-09-13 12:56:06 -0600 ECMDB00098 M2MDB000037 D-Xylose Xylose 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. &alpha;-D-xylose a-D-Xylose Alpha-D-Xylose D-(+)-Xylose D-Xylo-pentose D-Xylose Wood sugar Xylo-pfan Xylomed Xylose Xyloside α-D-Xylose C5H10O5 150.1299 150.05282343 (3R,4S,5R)-oxane-2,3,4,5-tetrol d-xylose 58-86-6 O[C@@H]1COC(O)[C@H](O)[C@H]1O InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1 SRBFZHDQGSBBOR-IOVATXLUSA-N Solid Cytosol Extra-organism Periplasm logp -2.57 ALOGPS logs 0.91 ALOGPS solubility 1.22e+03 g/l ALOGPS melting_point 90.5 oC logp -2.3 ChemAxon pka_strongest_acidic 11.31 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (3R,4S,5R)-oxane-2,3,4,5-tetrol ChemAxon average_mass 150.1299 ChemAxon mono_mass 150.05282343 ChemAxon smiles O[C@@H]1COC(O)[C@H](O)[C@H]1O ChemAxon formula C5H10O5 ChemAxon inchi InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1 ChemAxon inchikey SRBFZHDQGSBBOR-IOVATXLUSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 29.96 ChemAxon polarizability 13.43 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 4 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 Amino sugar and nucleotide sugar metabolism ec00520 Pentose and glucuronate interconversions ec00040 ABC transporters ec02010 Specdb::CMs 25082 Specdb::CMs 37293 Specdb::CMs 102604 Specdb::CMs 102605 Specdb::CMs 102606 Specdb::CMs 102607 Specdb::CMs 158325 Specdb::CMs 1049954 Specdb::CMs 1049955 Specdb::CMs 1049957 Specdb::CMs 1049959 Specdb::CMs 1049961 Specdb::CMs 1049963 Specdb::CMs 1049964 Specdb::CMs 1049966 Specdb::CMs 1049968 Specdb::CMs 1049970 Specdb::CMs 1049972 Specdb::CMs 1049974 Specdb::CMs 1049976 Specdb::CMs 1049977 Specdb::CMs 1049979 Specdb::CMs 1049981 Specdb::CMs 1049983 Specdb::CMs 1049985 Specdb::NmrOneD 1083 Specdb::NmrOneD 1145 Specdb::NmrOneD 142170 Specdb::NmrOneD 142171 Specdb::NmrOneD 142172 Specdb::NmrOneD 142173 Specdb::NmrOneD 142174 Specdb::NmrOneD 142175 Specdb::NmrOneD 142176 Specdb::NmrOneD 142177 Specdb::NmrOneD 142178 Specdb::NmrOneD 142179 Specdb::NmrOneD 142180 Specdb::NmrOneD 142181 Specdb::NmrOneD 142182 Specdb::NmrOneD 142183 Specdb::NmrOneD 142184 Specdb::NmrOneD 142185 Specdb::NmrOneD 142186 Specdb::NmrOneD 142187 Specdb::NmrOneD 142188 Specdb::NmrOneD 142189 Specdb::MsMs 153 Specdb::MsMs 154 Specdb::MsMs 155 Specdb::MsMs 321589 Specdb::MsMs 321590 Specdb::MsMs 321591 Specdb::MsMs 369244 Specdb::MsMs 369245 Specdb::MsMs 369246 Specdb::MsMs 2227272 Specdb::MsMs 2227432 Specdb::MsMs 2229628 Specdb::MsMs 2229866 Specdb::MsMs 2234459 Specdb::MsMs 2234480 Specdb::MsMs 2677755 Specdb::MsMs 2677756 Specdb::MsMs 2677757 Specdb::MsMs 3030968 Specdb::MsMs 3030969 Specdb::MsMs 3030970 Specdb::NmrTwoD 956 Specdb::NmrTwoD 1141 HMDB00098 135191 119104 C00181 15936 XYLOSE Xylose 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 Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. 2026685 Saliba F, Hagipantelli R, Misset JL, Bastian G, Vassal G, Bonnay M, Herait P, Cote C, Mahjoubi M, Mignard D, Cvitkovic E: Pathophysiology and therapy of irinotecan-induced delayed-onset diarrhea in patients with advanced colorectal cancer: a prospective assessment. J Clin Oncol. 1998 Aug;16(8):2745-51. 9704727 Weiner R, Dietze F, Laue R: Age-dependent alterations of intestinal absorption. II. A clinical study using a modified D-xylose absorption test. Arch Gerontol Geriatr. 1984 Jul;3(2):97-108. 6548110 Molina JM, Tourneur M, Sarfati C, Chevret S, de Gouvello A, Gobert JG, Balkan S, Derouin F: Fumagillin treatment of intestinal microsporidiosis. N Engl J Med. 2002 Jun 20;346(25):1963-9. 12075057 Kost S, Keinert K, Glaser FH: [D-xylose test of resorption as a method to determine radiation side effects in the small intestine] Strahlenther Onkol. 1998 Sep;174(9):462-7. 9765687 Weiner R, Laue R, Dietze F: [Enteral resorption kinetics in the aging process] Z Gesamte Inn Med. 1986 Mar 1;41(5):152-8. 3716508 Ehrenpreis ED, Salvino M, Craig RM: Improving the serum D-xylose test for the identification of patients with small intestinal malabsorption. J Clin Gastroenterol. 2001 Jul;33(1):36-40. 11418788 Weiner R: [Characteristics of disease and involution-induced changes in intestinal absorption] ZFA. 1986 Jul-Aug;41(4):219-24. 3751145 Weiner R, Laue R, Dietze F, Hartig W: A modified D-xylose absorption test. Infusionsther Klin Ernahr. 1984 Dec;11(6):333-7. 6526497 Horvath K, Horn G, Bingadeem H, Nemes Nagy A, Bodanszky H: [The value of the d-xylose loading test in the diagnosis of malabsorption syndromes] Orv Hetil. 1990 Aug 19;131(33):1803-6, 1809. 2204861 Wang SC, You RD: [Clinical and experimental study on treatment of anorexy in children with the activating spleen prescription] Zhong Xi Yi Jie He Za Zhi. 1991 Feb;11(2):75-8, 67. 2060054 Lavarack, B. P.; Griffin, G.; Rodman, D. Optimizing the autohydrolysis of bagasse to extract D-xylose. 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?1358894054 Xylose isomerase P00944 XYLA_ECOLI xylA http://ecmdb.ca/proteins/P00944.xml Xylose import ATP-binding protein XylG P37388 XYLG_ECOLI xylG http://ecmdb.ca/proteins/P37388.xml Putative beta-xylosidase P77713 YAGH_ECOLI yagH http://ecmdb.ca/proteins/P77713.xml Xylose transport system permease protein xylH P0AGI4 XYLH_ECOLI xylH http://ecmdb.ca/proteins/P0AGI4.xml D-xylose-binding periplasmic protein P37387 XYLF_ECOLI xylF http://ecmdb.ca/proteins/P37387.xml Xylose import ATP-binding protein XylG P37388 XYLG_ECOLI xylG http://ecmdb.ca/proteins/P37388.xml D-xylose-proton symporter P0AGF4 XYLE_ECOLI xylE http://ecmdb.ca/proteins/P0AGF4.xml Xylose transport system permease protein xylH P0AGI4 XYLH_ECOLI xylH http://ecmdb.ca/proteins/P0AGI4.xml D-xylose-binding periplasmic protein P37387 XYLF_ECOLI xylF http://ecmdb.ca/proteins/P37387.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Adenosine triphosphate + Water + D-Xylose > ADP + Hydrogen ion + Phosphate + D-Xylose ABC-33-RXN Adenosine triphosphate + Water + D-Xylose > ADP + Hydrogen ion + Phosphate + D-Xylose ABC-33-RXN D-Xylose <> D-Xylulose R01432 D-Xylose + 1,4-beta-D-Xylan <> 1,4-beta-D-Xylan + Water R01433 Adenosine triphosphate + D-Xylose + Water > ADP + Phosphate + D-Xylose + Hydrogen ion ABC-33-RXN Adenosine triphosphate + D-Xylose + Water > ADP + Phosphate + D-Xylose + Hydrogen ion ABC-33-RXN isoprimeverose + Water b-D-Glucose + D-Xylose RXN-12402 xylan + Water D-Xylose RXN0-5001 D-Xylose > D-Xylulose