2.0 2012-05-31 14:40:08 -0600 2015-07-07 11:22:39 -0600 ECMDB20344 M2MDB001173 beta-D-Ribopyranose Beta-D-ribopyranose is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Ribose 5-phosphate is involved in the pentose phosphate pathway and ribose degradation. The pentose phosphate pathway plays several key roles in metabolism including supply of biosynthetic carbon skeletons and reducing power. (PMID 9546650) Ribose-5-phosphate isomerase A (RpiA) plays an important role in interconverting between ribose-5-phosphate (R5P) and ribulose-5-phosphate in the pentose phosphate pathway and the Calvin cycle. (PMID 19214439). In Escherichia coli, RpiA catalyzes the interconversion of ribose-5-phosphate and ribulose-5-phosphate and is a key enzyme in the pentose phosphate pathway. (PMID 12182339). 5-(Dihydrogen phosphate)D-Ribose 5-(Dihydrogen phosphoric acid)D-ribose 5-O-Phosphono-D-ribose b-D-Ribopyranose D-Ribofuranose, 5-(dihydrogen phosphate) D-Ribofuranose, 5-(dihydrogen phosphoric acid) D-Ribose D-Ribose 5-(dihydrogen phosphate) D-Ribose 5-(dihydrogen phosphoric acid) D-Ribose 5-phosphate D-Ribose 5-phosphoric acid D-Ribose, 5-(dihydrogen phosphate) D-Ribose, 5-(dihydrogen phosphoric acid) D-Ribose-5-P D-Ribose-5-phosphate D-Ribose-5-phosphorate D-Ribose-5-phosphoric acid Pentose Ribose Ribose 5-monophosphate Ribose 5-monophosphoric acid Ribose 5-phosphate Ribose 5-phosphoric acid Ribose phosphate Ribose phosphoric acid Ribose, 5-(dihydrogen phosphate) Ribose, 5-(dihydrogen phosphoric acid) Ribose-5-P Ribose-5-phosphate Ribose-5-phosphorate Ribose-5-phosphoric acid Ribose-5P β-D-Ribopyranose C5H10O5 150.1299 150.05282343 (2R,3R,4R,5R)-oxane-2,3,4,5-tetrol β-D-ribopyranose 50-69-1 O[C@@H]1CO[C@@H](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-TXICZTDVSA-N Solid Cytoplasm Periplasm logp -2.57 ALOGPS logs 0.91 ALOGPS solubility 1.22e+03 g/l ALOGPS melting_point 95 oC logp -2.3 ChemAxon pka_strongest_acidic 11.31 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (2R,3R,4R,5R)-oxane-2,3,4,5-tetrol ChemAxon average_mass 150.1299 ChemAxon mono_mass 150.05282343 ChemAxon smiles O[C@@H]1CO[C@@H](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-TXICZTDVSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 29.96 ChemAxon polarizability 13.39 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon ABC transporters ec02010 Ribose Degradation D-ribose, which can serve as a total source of carbon and energy for E. coli, enters the cell via a high-affinity ABC transport system and hence in unphosphorylated form. The crystal structure of the periplasmic ribose binding protein of the ribose ABC transporter showed it to bind (and thus presumably to facilitate transport of) β-D-ribopyranose. ribose pyranase accelerates the conversion between the pyranose and furanose forms of β-D-ribose. Interconversion of the α- and β-anomers of D-ribofuranose is fast and spontaneous. ribokinase then converts it to D-ribose 5-phosphate, an intermediate of the pentose phosphate pathway, and hence it flows through the pathways of central metabolism to satisfy the cell's need for precursor metabolites, reducing power, and metabolic energy. (EcoCyc) PW002102 Metabolic ribose degradation RIBOKIN-PWY Specdb::CMs 24968 Specdb::CMs 39855 Specdb::NmrOneD 254288 Specdb::NmrOneD 254289 Specdb::NmrOneD 254290 Specdb::NmrOneD 254291 Specdb::NmrOneD 254292 Specdb::NmrOneD 254293 Specdb::NmrOneD 254294 Specdb::NmrOneD 254295 Specdb::NmrOneD 254296 Specdb::NmrOneD 254297 Specdb::NmrOneD 254298 Specdb::NmrOneD 254299 Specdb::NmrOneD 254300 Specdb::NmrOneD 254301 Specdb::NmrOneD 254302 Specdb::NmrOneD 254303 Specdb::NmrOneD 254304 Specdb::NmrOneD 254305 Specdb::NmrOneD 254306 Specdb::NmrOneD 254307 Specdb::MsMs 28034 Specdb::MsMs 28035 Specdb::MsMs 28036 Specdb::MsMs 34592 Specdb::MsMs 34593 Specdb::MsMs 34594 HMDB12194 441481 5575 C08353 27476 CPD0-1110 RIP 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 Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. 18402659 Buchholz, A., Takors, R., Wandrey, C. (2001). "Quantification of intracellular metabolites in Escherichia coli K12 using liquid chromatographic-electrospray ionization tandem mass spectrometric techniques." Anal Biochem 295:129-137. 11488613 Ribose import ATP-binding protein RbsA P04983 RBSA_ECOLI rbsA http://ecmdb.ca/proteins/P04983.xml Ribose transport system permease protein rbsC P0AGI1 RBSC_ECOLI rbsC http://ecmdb.ca/proteins/P0AGI1.xml D-ribose pyranase P04982 RBSD_ECOLI rbsD http://ecmdb.ca/proteins/P04982.xml D-ribose-binding periplasmic protein P02925 RBSB_ECOLI rbsB http://ecmdb.ca/proteins/P02925.xml Ribose import ATP-binding protein RbsA P04983 RBSA_ECOLI rbsA http://ecmdb.ca/proteins/P04983.xml Sugar efflux transporter C P31436 SETC_ECOLI setC http://ecmdb.ca/proteins/P31436.xml Ribose transport system permease protein rbsC P0AGI1 RBSC_ECOLI rbsC http://ecmdb.ca/proteins/P0AGI1.xml D-ribose-binding periplasmic protein P02925 RBSB_ECOLI rbsB http://ecmdb.ca/proteins/P02925.xml beta-D-Ribopyranose <> beta-D-ribofuranose R08247 RXN0-5304 Adenosine triphosphate + beta-D-Ribopyranose + Water > ADP + Phosphate + beta-D-Ribopyranose + Hydrogen ion ABC-28-RXN Adenosine triphosphate + beta-D-Ribopyranose + Water > ADP + Phosphate + beta-D-Ribopyranose + Hydrogen ion ABC-28-RXN beta-D-ribofuranose <> beta-D-Ribopyranose RXN0-5304 beta-D-Ribopyranose > beta-D-ribofuranose beta-D-Ribopyranose + Adenosine triphosphate + Water > ADP + Phosphate + Hydrogen ion PW_RCT000194 0.2 g/L NH4Cl, 2.0 g/L (NH4)2SO4, 3.25 g/L KH2PO4, 2.5 g/L K2HPO4, 1.5 g/L NaH2PO4, 0.5 g/L MgSO4; trace substances: 10 mg/L CaCl2, 0.5 mg/L ZnSO4, 0.25 mg/L CuCl2, 0.25 mg/L MnSO4, 0.175 mg/L CoCl2, 0.125 mg/L H3BO3, 2.5 mg/L AlCl3, 0.5 mg/L Na2MoO4, 10 Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h 260.0 uM 21.0 37 oC K12 Stationary Phase, glucose limited 1040000 84000 Buchholz, A., Takors, R., Wandrey, C. (2001). "Quantification of intracellular metabolites in Escherichia coli K12 using liquid chromatographic-electrospray ionization tandem mass spectrometric techniques." Anal Biochem 295:129-137. 11488613