2.02012-05-31 10:21:39 -06002015-09-13 12:56:06 -0600ECMDB00132M2MDB000051GuanineGuanine is one of the five main nucleobases found in the nucleic acids DNA and RNA. Guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. Being unsaturated, the bicyclic molecule is planar. The guanine nucleoside is called guanosine. High affinity binding of guanine nucleotides and the ability to hydrolyze bound GTP to GDP are characteristics of an extended family of intracellular proteins. Hypoxanthine-guanine phosphoribosyltransferase (HPRT, EC 2.4.2.8) is a purine salvage enzyme that catalyses the conversion of hypoxanthine and guanine to their respective mononucleotides. Peroxynitrite induces DNA base damage predominantly at guanine (G) and 8-oxoguanine (8-oxoG) nucleobases via oxidation reactions. G and 8-oxoG are the most reactive bases toward Peroxynitrite and possibly the major contributors to peroxynitrite-derived genotoxic and mutagenic lesions. The neutral G radical, reacts with NO2 to yield 8-nitroguanine and 5-nitro-4-guanidinohydantoin. (PMID: 16352449, 2435586)2-Amino-1,7-dihydro-6H-Purin-6-one2-Amino-1,9-dihydro-6H-purin-6-one2-Amino-1,9-dihydro-purin-6-one2-Amino-3,7-dihydro-6H-purin-6-one2-Amino-6-hydroxy-1H-purine2-Amino-6-hydroxypurine2-Amino-6-purinol2-Amino-Hypoxanthine2-Aminohypoxanthine6-Hydroxy-2-aminopurineC.I. Natural White 1CI Natural white 1Dew PearlGUAGuaninGuanineGuanine enolGUNMearlmaidMearlmaid AANatural pearl essenceNatural White 1NaturonPathocidinPearl EssenceStella PolarisC5H5N5O151.1261151.0494098072-amino-6,7-dihydro-3H-purin-6-one2-aminohypoxanthine73-40-5NC1=NC(=O)C2=C(N1)N=CN2InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)UYTPUPDQBNUYGX-UHFFFAOYSA-NSolidCytosolExtra-organismPeriplasmlogp-0.92logs-1.82solubility2.31e+00 g/lmelting_point360 oClogp-0.59pka_strongest_acidic8.95pka_strongest_basic2.22iupac2-amino-6,7-dihydro-3H-purin-6-oneaverage_mass151.1261mono_mass151.049409807smilesNC1=NC(=O)C2=C(N1)N=CN2formulaC5H5N5OinchiInChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)inchikeyUYTPUPDQBNUYGX-UHFFFAOYSA-Npolar_surface_area96.16refractivity38.9polarizability13.34rotatable_bond_count0acceptor_count5donor_count3physiological_charge0formal_charge0Purine metabolismec00230Metabolic pathwayseco01100preQ0 metabolismPreQ0 or 7-cyano-7-carbaguanine is biosynthesized by degrading GTP.
GTP first interacts with water through a GTP cyclohydrolase resulting in the release of a formate, a hydrogen ion and a 7,8-dihydroneopterin 3'-triphosphate. The latter compound then interacts with water through a 6-carboxy-5,6,7,8-tetrahydropterin synthase resulting in a acetaldehyde, triphosphate, 2 hydrogen ion and 6-carboxy-5,6,7,8-tetrahydropterin. The latter compound then reacts spontaneously with a hydrogen ion resulting in the release of a ammonium molecule and a 7-carboxy-7-deazaguanine. This compound then interacts with ATP and ammonium through 7-cyano-7-deazaguanine synthase resulting in the release of water, phosphate, ADP, hydrogen ion and a 7-cyano-7-carbaguanine.
The degradation of 7-cyano-7-deazaguanine can lead to produce a preQ1 or a queuine by reacting with 3 hydrogen ions and 2 NADPH through a 7-cyano-7-deazaguanine reductase. PreQ1 then interacts with a guanine 34 in tRNA through a tRNA-guanine transglycosylase resulting in a release of a guanine and a 7-aminomethyl-7-deazaguanosine 34 in tRNA. This nucleic acid then interacts with SAM through a S-adenosylmethionine tRNA ribosyltransferase-isomerase resulting in a release of a hydrogen ion, L-methionine, adenine and an epoxyqueuosinePW001893Metabolicguanine 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 deoxyribonucleosides degradationPW002077Metabolicpurine 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-phosphatePWY0-1296purine deoxyribonucleosides degradationPWY0-1297queuosine biosynthesisPWY-6700guanosine nucleotides degradation IIIPWY-6608guanine and guanosine salvage IPWY-6620Specdb::CMs861Specdb::CMs1824Specdb::CMs3036Specdb::CMs29897Specdb::CMs30563Specdb::CMs31016Specdb::CMs31820Specdb::CMs31821Specdb::CMs163048Specdb::EiMs1803Specdb::NmrOneD1102Specdb::NmrOneD4947Specdb::NmrOneD4948Specdb::NmrOneD142430Specdb::NmrOneD142431Specdb::NmrOneD142432Specdb::NmrOneD142433Specdb::NmrOneD142434Specdb::NmrOneD142435Specdb::NmrOneD142436Specdb::NmrOneD142437Specdb::NmrOneD142438Specdb::NmrOneD142439Specdb::NmrOneD142440Specdb::NmrOneD142441Specdb::NmrOneD142442Specdb::NmrOneD142443Specdb::NmrOneD142444Specdb::NmrOneD142445Specdb::NmrOneD142446Specdb::NmrOneD142447Specdb::NmrOneD142448Specdb::NmrOneD142449Specdb::NmrOneD166581Specdb::MsMs6223Specdb::MsMs6224Specdb::MsMs6225Specdb::MsMs6226Specdb::MsMs6227Specdb::MsMs6228Specdb::MsMs6229Specdb::MsMs6230Specdb::MsMs6231Specdb::MsMs6232Specdb::MsMs6233Specdb::MsMs6234Specdb::MsMs6236Specdb::MsMs6237Specdb::MsMs19967Specdb::MsMs19968Specdb::MsMs19969Specdb::MsMs21518Specdb::MsMs21519Specdb::MsMs21520Specdb::MsMs438628Specdb::MsMs438828Specdb::MsMs438829Specdb::MsMs439072Specdb::MsMs440048Specdb::NmrTwoD964Specdb::NmrTwoD1160HMDB00132764744C0024216235GUANINEGUNGuanineKeseler, I. 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Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.http://hmdb.ca/system/metabolites/msds/000/000/092/original/HMDB00132.pdf?1358894467Queuine tRNA-ribosyltransferaseP0A847TGT_ECOLItgthttp://ecmdb.ca/proteins/P0A847.xmlHypoxanthine phosphoribosyltransferaseP0A9M2HPRT_ECOLIhpthttp://ecmdb.ca/proteins/P0A9M2.xmlXanthine phosphoribosyltransferaseP0A9M5XGPT_ECOLIgpthttp://ecmdb.ca/proteins/P0A9M5.xmlPurine nucleoside phosphorylase deoD-typeP0ABP8DEOD_ECOLIdeoDhttp://ecmdb.ca/proteins/P0ABP8.xmlPyrimidine-specific ribonucleoside hydrolase rihBP33022RIHB_ECOLIrihBhttp://ecmdb.ca/proteins/P33022.xmlAdenine phosphoribosyltransferaseP69503APT_ECOLIapthttp://ecmdb.ca/proteins/P69503.xmlGuanine deaminaseP76641GUAD_ECOLIguaDhttp://ecmdb.ca/proteins/P76641.xmlXanthosine phosphorylaseP45563XAPA_ECOLIxapAhttp://ecmdb.ca/proteins/P45563.xmlXanthine permease XanPP0AGM9XANP_ECOLIxanPhttp://ecmdb.ca/proteins/P0AGM9.xmlNucleoside-specific channel-forming protein tsxP0A927TSX_ECOLItsxhttp://ecmdb.ca/proteins/P0A927.xmlGuanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + PyrophosphateR01229GUANPRIBOSYLTRAN-RXNDeoxyguanosine + Phosphate <> Deoxyribose 1-phosphate + GuanineR01969Guanosine + Phosphate <> Guanine + Ribose-1-phosphateRXN0-5199Guanine + Hydrogen ion + Water > Ammonium + XanthineGuanosine monophosphate + Pyrophosphate <> Guanine + Phosphoribosyl pyrophosphateR01229Guanine + Water <> Xanthine + AmmoniaR01676GUANINE-DEAMINASE-RXNGuanosine + Water <> Guanine + RiboseR01677Guanosine + Phosphate <> Guanine + alpha-D-Ribose 1-phosphateR02147Deoxyguanosine + Phosphate <> deoxyribose-1-phosphate + GuanineDEOXYGUANPHOSPHOR-RXNWater + Guanine > Ammonia + XanthineGUANINE-DEAMINASE-RXNGuanine(34) in tRNA + Queuine > queuosine(34) in tRNA + GuanineGuanine(34) in tRNA + 7-Aminomethyl-7-carbaguanine > 7-aminomethyl-7-carbaguanine(34) in tRNA + GuanineQueuine + 7-Aminomethyl-7-carbaguanine <> GuanineR03789 7-Aminomethyl-7-carbaguanine + tRNA guanine > 7-aminomethyl-7-deazaguanosine34 in tRNA + GuaninePW_R005183Guanosine + Phosphate > Ribose-1-phosphate + GuaninePW_R006058Guanine + Phosphoribosyl pyrophosphate > Pyrophosphate + Guanosine monophosphatePW_R006059Guanine + Water <> Xanthine + AmmoniaGuanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + PyrophosphateQueuine + 7 7-Aminomethyl-7-carbaguanine <> GuanineGuanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + PyrophosphateQueuine + 7 7-Aminomethyl-7-carbaguanine <> GuanineGutnick 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 culture188.0uM0.037 oCK12 NCM3722Mid-Log Phase7520000Bennett, 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 5:593-599.19561621Gutnick 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 glycerolShake flask and filter culture3.13uM0.037 oCK12 NCM3722Mid-Log Phase125200Bennett, 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 5:593-599.19561621Gutnick 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 acetateShake flask and filter culture3.13uM0.037 oCK12 NCM3722Mid-Log Phase125200Bennett, 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/h65.1uM0.037 oCBW25113Stationary Phase, glucose limited2604000Ishii, 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