2.02012-08-09 09:16:18 -06002015-06-03 17:21:33 -0600ECMDB21456M2MDB0018517-Aminomethyl-7-carbaguanine7-Aminomethyl-7-carbaguanine is one of the precursors of nucleoside Q (queuosine) biosynthesis. It is a substrate for preQ1 synthase (EC 1.7.1.13) which catalyzes the NADPH-dependent reduction of 7-cyano-7-carbaguanine (preQ0) to 7-aminomethyl-7-carbaguanine (preQ1). More specifically, this enzyme catalyzes the chemical reaction7-Aminomethyl-7-carbaguanine7-Aminomethyl-7-deazaguaninePreQ1C7H9N5O179.1793179.0807099352-amino-5-(aminomethyl)-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one7-aminomethyl-7-deazaguanineNCC1=CNC2=C1C(=O)NC(N)=N2InChI=1S/C7H9N5O/c8-1-3-2-10-5-4(3)6(13)12-7(9)11-5/h2H,1,8H2,(H4,9,10,11,12,13)MEYMBLGOKYDGLZ-UHFFFAOYSA-NSolidCytoplasmlogp-1.43logs-1.79solubility2.93e+00 g/llogp-1.2pka_strongest_acidic11.04pka_strongest_basic8.6iupac2-amino-5-(aminomethyl)-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-oneaverage_mass179.1793mono_mass179.080709935smilesNCC1=CNC2=C1C(=O)NC(N)=N2formulaC7H9N5OinchiInChI=1S/C7H9N5O/c8-1-3-2-10-5-4(3)6(13)12-7(9)11-5/h2H,1,8H2,(H4,9,10,11,12,13)inchikeyMEYMBLGOKYDGLZ-UHFFFAOYSA-Npolar_surface_area109.29refractivity48.67polarizability17.44rotatable_bond_count1acceptor_count4donor_count4physiological_charge1formal_charge0Folate biosynthesisThe biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.
Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid.
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate.
This product goes on to a one carbon pool by folate pathway.
PW000908ec00790MetabolicMetabolic 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 epoxyqueuosinePW001893MetabolicSpecdb::CMs10409Specdb::CMs173383Specdb::NmrOneD94032Specdb::NmrOneD94033Specdb::NmrOneD94034Specdb::NmrOneD94035Specdb::NmrOneD94036Specdb::NmrOneD94037Specdb::NmrOneD94038Specdb::NmrOneD94039Specdb::NmrOneD94040Specdb::NmrOneD94041Specdb::NmrOneD94042Specdb::NmrOneD94043Specdb::NmrOneD94044Specdb::NmrOneD94045Specdb::NmrOneD94046Specdb::NmrOneD94047Specdb::NmrOneD94048Specdb::NmrOneD94049Specdb::NmrOneD94050Specdb::NmrOneD94051Specdb::MsMs27539Specdb::MsMs27540Specdb::MsMs27541Specdb::MsMs34097Specdb::MsMs34098Specdb::MsMs34099Specdb::MsMs2398125Specdb::MsMs2398126Specdb::MsMs2398127Specdb::MsMs2536895Specdb::MsMs2536896Specdb::MsMs2536897HMDB11690171166C16675PRFWinder, 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 80:2939-2948.18331064Queuine tRNA-ribosyltransferaseP0A847TGT_ECOLItgthttp://ecmdb.ca/proteins/P0A847.xmlNADPH-dependent 7-cyano-7-deazaguanine reductaseQ46920QUEF_ECOLIqueFhttp://ecmdb.ca/proteins/Q46920.xml7-Aminomethyl-7-carbaguanine + 2 NADP > 7-Cyano-7-carbaguanine +2 NADPHGuanine(34) in tRNA + 7-Aminomethyl-7-carbaguanine > 7-aminomethyl-7-carbaguanine(34) in tRNA + GuanineQueuine + 7-Aminomethyl-7-carbaguanine <> GuanineR03789 7-Aminomethyl-7-carbaguanine + NADP <> 7-Cyano-7-carbaguanine + NADPH +2 Hydrogen ionR07605 7-Cyano-7-carbaguanine + 3 Hydrogen ion + 2 NADPH + 2 NADPH >2 NADP + 7-Aminomethyl-7-carbaguaninePW_R0051817-Aminomethyl-7-carbaguanine + tRNA guanine > 7-aminomethyl-7-deazaguanosine34 in tRNA + GuaninePW_R0051837 7-Aminomethyl-7-carbaguanine + NADP <>7 7-Cyano-7-carbaguanine + NADPH +2 Hydrogen ionQueuine + 7 7-Aminomethyl-7-carbaguanine <> GuanineQueuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine