2.0 2012-08-09 09:16:18 -0600 2015-06-03 17:21:33 -0600 ECMDB21456 M2MDB001851 7-Aminomethyl-7-carbaguanine 7-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 reaction 7-Aminomethyl-7-carbaguanine 7-Aminomethyl-7-deazaguanine PreQ1 C7H9N5O 179.1793 179.080709935 2-amino-5-(aminomethyl)-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one 7-aminomethyl-7-deazaguanine NCC1=CNC2=C1C(=O)NC(N)=N2 InChI=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-N Solid Cytoplasm logp -1.43 ALOGPS logs -1.79 ALOGPS solubility 2.93e+00 g/l ALOGPS logp -1.2 ChemAxon pka_strongest_acidic 11.04 ChemAxon pka_strongest_basic 8.6 ChemAxon iupac 2-amino-5-(aminomethyl)-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one ChemAxon average_mass 179.1793 ChemAxon mono_mass 179.080709935 ChemAxon smiles NCC1=CNC2=C1C(=O)NC(N)=N2 ChemAxon formula C7H9N5O ChemAxon inchi InChI=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) ChemAxon inchikey MEYMBLGOKYDGLZ-UHFFFAOYSA-N ChemAxon polar_surface_area 109.29 ChemAxon refractivity 48.67 ChemAxon polarizability 17.44 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Folate biosynthesis The 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. PW000908 ec00790 Metabolic Metabolic pathways eco01100 preQ0 metabolism PreQ0 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 epoxyqueuosine PW001893 Metabolic Specdb::CMs 10409 Specdb::CMs 173383 Specdb::NmrOneD 94032 Specdb::NmrOneD 94033 Specdb::NmrOneD 94034 Specdb::NmrOneD 94035 Specdb::NmrOneD 94036 Specdb::NmrOneD 94037 Specdb::NmrOneD 94038 Specdb::NmrOneD 94039 Specdb::NmrOneD 94040 Specdb::NmrOneD 94041 Specdb::NmrOneD 94042 Specdb::NmrOneD 94043 Specdb::NmrOneD 94044 Specdb::NmrOneD 94045 Specdb::NmrOneD 94046 Specdb::NmrOneD 94047 Specdb::NmrOneD 94048 Specdb::NmrOneD 94049 Specdb::NmrOneD 94050 Specdb::NmrOneD 94051 Specdb::MsMs 27539 Specdb::MsMs 27540 Specdb::MsMs 27541 Specdb::MsMs 34097 Specdb::MsMs 34098 Specdb::MsMs 34099 Specdb::MsMs 2398125 Specdb::MsMs 2398126 Specdb::MsMs 2398127 Specdb::MsMs 2536895 Specdb::MsMs 2536896 Specdb::MsMs 2536897 HMDB11690 171 166 C16675 PRF 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 Queuine tRNA-ribosyltransferase P0A847 TGT_ECOLI tgt http://ecmdb.ca/proteins/P0A847.xml NADPH-dependent 7-cyano-7-deazaguanine reductase Q46920 QUEF_ECOLI queF http://ecmdb.ca/proteins/Q46920.xml 7-Aminomethyl-7-carbaguanine + 2 NADP > 7-Cyano-7-carbaguanine +2 NADPH Guanine(34) in tRNA + 7-Aminomethyl-7-carbaguanine > 7-aminomethyl-7-carbaguanine(34) in tRNA + Guanine Queuine + 7-Aminomethyl-7-carbaguanine <> Guanine R03789 7-Aminomethyl-7-carbaguanine + NADP <> 7-Cyano-7-carbaguanine + NADPH +2 Hydrogen ion R07605 7-Cyano-7-carbaguanine + 3 Hydrogen ion + 2 NADPH + 2 NADPH >2 NADP + 7-Aminomethyl-7-carbaguanine PW_R005181 7-Aminomethyl-7-carbaguanine + tRNA guanine > 7-aminomethyl-7-deazaguanosine34 in tRNA + Guanine PW_R005183 7 7-Aminomethyl-7-carbaguanine + NADP <>7 7-Cyano-7-carbaguanine + NADPH +2 Hydrogen ion Queuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine Queuine + 7 7-Aminomethyl-7-carbaguanine <> Guanine