2.02012-05-31 10:21:42 -06002015-09-13 12:56:06 -0600ECMDB00133M2MDB000052GuanosineGuanosine is a nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a beta-N9-glycosidic bond. Guanosine can be phosphorylated to become GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate) and GTP (guanosine triphosphate). (Wikipedia)2-Amino-1,9-dihydro-9-b-D-ribofuranosyl-6H-purin-6-one2-amino-1,9-dihydro-9-b-delta-Ribofuranosyl-6H-purin-6-one2-amino-1,9-dihydro-9-b-δ-Ribofuranosyl-6H-purin-6-one2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one2-Amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one2-amino-1,9-dihydro-9-β-D-Ribofuranosyl-6H-purin-6-one2-amino-1,9-dihydro-9-β-δ-Ribofuranosyl-6H-purin-6-one2-Amino-Inosine9-b-D-ribofuranosyl-Guanine9-b-delta-Ribofuranosyl-guanine9-b-δ-Ribofuranosyl-guanine9-beta-D-Ribofuranosyl-Guanine9-beta-delta-Ribofuranosyl-Guanine9-β-D-Ribofuranosyl-guanine9-β-δ-Ribofuranosyl-guanineB-D-Ribofuranoside guanine-9b-delta-Ribofuranoside guanine-9b-δ-Ribofuranoside guanine-9Beta-D-Ribofuranoside guanine-9Beta-delta-Ribofuranoside guanine-9GuanosineNucleoside QRibonucleosideVernineβ-D-Ribofuranoside guanine-9β-δ-Ribofuranoside guanine-9C10H13N5O5283.2407283.0916685512-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-oneguanosine118-00-3NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1NYHBQMYGNKIUIF-UUOKFMHZSA-NSolidCytosolExtra-organismPeriplasmlogp-2.06logs-1.27solubility1.53e+01 g/lmelting_point239 oClogp-2.7pka_strongest_acidic10.16pka_strongest_basic0.45iupac2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-oneaverage_mass283.2407mono_mass283.091668551smilesNC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1formulaC10H13N5O5inchiInChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1inchikeyNYHBQMYGNKIUIF-UUOKFMHZSA-Npolar_surface_area155.22refractivity64.62polarizability26.03rotatable_bond_count2acceptor_count8donor_count5physiological_charge0formal_charge0Purine metabolismec00230guanine and guanosine salvageGuanosine can be converted into guanine through a phosphate driven guanosine phosphorylase resulting in the release of an alpha-D-ribose 1 phosphate and a guanine. This compound in turn reacts with a PRPP through a guanine phosphoribosyltransferase resulting in the release of a pyrophosphate and a GMP.
Guanosine can also react with and ATP driven guanosine kinase resulting in the release of an ADP, s hydrogen ion and a GMP
PW002074Metabolicpurine ribonucleosides degradationPurine ribonucleoside degradation leads to the production of alpha-D-ribose-1-phosphate.
Xanthosine is transported into the cytosol through a xapB. Once in the cytosol xanthosine interacts with phosphate through a xanthosine phosphorylase resulting in the release of a xanthine and a alpha-D-ribose-1-phosphate.
Adenosine is transported through a nupC or a nupG transporter, once inside the cytosol it can either react with a phosphate through a adenosine phosphorylase resultin in the release of a adenine and an alpha-D-ribose-1-phosphate. Adenosine reacts with water and hydrogen ion through a adenosine deaminase resulting in the release of ammonium and inosine. Inosine reacts with phosphate through a inosine phosphorylase resulting in the release of a hypoxanthine and an alpha-D-ribose-1-phosphate.
Guanosine reacts with a phosphate through a guanosine phosphorylase resulting in the release of a guanine and a alpha-D-ribose-1-phosphate.PW002076Metabolicpurine ribonucleosides degradation to ribose-1-phosphatePWY0-1296guanosine nucleotides degradation IIIPWY-6608guanine and guanosine salvage IPWY-6620guanine and guanosine salvage IIIPWY-6618Specdb::CMs356Specdb::CMs357Specdb::CMs358Specdb::CMs359Specdb::CMs2710Specdb::CMs30191Specdb::CMs30564Specdb::CMs30873Specdb::CMs30874Specdb::CMs37313Specdb::CMs131331Specdb::CMs139065Specdb::CMs1051195Specdb::CMs1051196Specdb::CMs1051197Specdb::CMs1051199Specdb::CMs1051201Specdb::CMs1051203Specdb::CMs1051205Specdb::CMs1051207Specdb::CMs1051209Specdb::CMs1051211Specdb::CMs1051213Specdb::CMs1051215Specdb::CMs1051217Specdb::EiMs1973Specdb::NmrOneD1103Specdb::NmrOneD1161Specdb::NmrOneD142450Specdb::NmrOneD142451Specdb::NmrOneD142452Specdb::NmrOneD142453Specdb::NmrOneD142454Specdb::NmrOneD142455Specdb::NmrOneD142456Specdb::NmrOneD142457Specdb::NmrOneD142458Specdb::NmrOneD142459Specdb::NmrOneD142460Specdb::NmrOneD142461Specdb::NmrOneD142462Specdb::NmrOneD142463Specdb::NmrOneD142464Specdb::NmrOneD142465Specdb::NmrOneD142466Specdb::NmrOneD142467Specdb::NmrOneD142468Specdb::NmrOneD142469Specdb::NmrOneD166526Specdb::NmrOneD166605Specdb::MsMs203Specdb::MsMs204Specdb::MsMs205Specdb::MsMs3006Specdb::MsMs3007Specdb::MsMs3008Specdb::MsMs3009Specdb::MsMs3010Specdb::MsMs3011Specdb::MsMs3012Specdb::MsMs3013Specdb::MsMs3014Specdb::MsMs3015Specdb::MsMs3016Specdb::MsMs3017Specdb::MsMs3018Specdb::MsMs3019Specdb::MsMs3020Specdb::MsMs3021Specdb::MsMs3022Specdb::MsMs3023Specdb::MsMs3024Specdb::MsMs3025Specdb::MsMs3026Specdb::MsMs3027Specdb::NmrTwoD965Specdb::NmrTwoD1161HMDB0013368026544C0038716750GUANOSINEGMPGuanosineKeseler, I. 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Gongye Weishengwu (1998), 28(4), 11-16. http://hmdb.ca/system/metabolites/msds/000/000/093/original/HMDB00133.pdf?1358894469Protein ushAP07024USHA_ECOLIushAhttp://ecmdb.ca/proteins/P07024.xml2',3'-cyclic-nucleotide 2'-phosphodiesterase/3'-nucleotidaseP08331CPDB_ECOLIcpdBhttp://ecmdb.ca/proteins/P08331.xmlMultifunctional protein surEP0A840SURE_ECOLIsurEhttp://ecmdb.ca/proteins/P0A840.xml5'-nucleotidase yjjGP0A8Y1YJJG_ECOLIyjjGhttp://ecmdb.ca/proteins/P0A8Y1.xmlPurine nucleoside phosphorylase deoD-typeP0ABP8DEOD_ECOLIdeoDhttp://ecmdb.ca/proteins/P0ABP8.xmlClass B acid phosphataseP0AE22APHA_ECOLIaphAhttp://ecmdb.ca/proteins/P0AE22.xmlInosine-guanosine kinaseP0AEW6INGK_ECOLIgskhttp://ecmdb.ca/proteins/P0AEW6.xmlDeoxyguanosinetriphosphate triphosphohydrolaseP15723DGTP_ECOLIdgthttp://ecmdb.ca/proteins/P15723.xmlPyrimidine-specific ribonucleoside hydrolase rihBP33022RIHB_ECOLIrihBhttp://ecmdb.ca/proteins/P33022.xml5'-nucleotidase yfbRP76491YFBR_ECOLIyfbRhttp://ecmdb.ca/proteins/P76491.xmlXanthosine phosphorylaseP45563XAPA_ECOLIxapAhttp://ecmdb.ca/proteins/P45563.xmlNucleoside permease nupGP0AFF4NUPG_ECOLInupGhttp://ecmdb.ca/proteins/P0AFF4.xmlNucleoside permease nupXP33021NUPX_ECOLInupXhttp://ecmdb.ca/proteins/P33021.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.xmlGuanosine monophosphate + Water > Guanosine + PhosphateGuanosine + Phosphate <> Guanine + Ribose-1-phosphateRXN0-5199Guanosine triphosphate + Water > Guanosine + TriphosphateAdenosine triphosphate + Guanosine > ADP + Guanosine monophosphate + Hydrogen ionR01228GUANOSINEKIN-RXNGuanosine 3'-phosphate + Water > Guanosine + PhosphateGuanosine monophosphate + Water <> Guanosine + PhosphateR01227Adenosine triphosphate + Guanosine <> ADP + Guanosine monophosphateR01228Guanosine + Water <> Guanine + RiboseR01677Guanosine + Phosphate <> Guanine + alpha-D-Ribose 1-phosphateR02147Guanosine + Phosphate > Ribose-1-phosphate + GuaninePW_R006058Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseShake flask and filter culture1.62uM0.037 oCK12 NCM3722Mid-Log Phase64800Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.1956162148 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h25.3uM0.037 oCBW25113Stationary Phase, glucose limited1012000Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597.17379776