2.02012-07-30 14:54:47 -06002015-06-03 17:20:49 -0600ECMDB21183M2MDB0015927-Deaza-7-carboxyguanine7-deaza-7-carboxyguanine is a member of the chemical class known as Pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. 2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-D]pyrimidine-5-carboxylate2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-D]pyrimidine-5-carboxylic acid7-Deaza-7-carboxyguanineC7H6N4O3194.1475194.0439900782-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid2-amino-4-oxo-1H,7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid[H]OC(=O)C1=C([H])N([H])C2=C1C(=O)N=C(N([H])[H])N2[H]InChI=1S/C7H6N4O3/c8-7-10-4-3(5(12)11-7)2(1-9-4)6(13)14/h1H,(H,13,14)(H4,8,9,10,11,12)XIUIRSLBMMTDSK-UHFFFAOYSA-NCytosollogp-0.51logs-1.82solubility2.96e+00 g/llogp-0.16pka_strongest_acidic5.21pka_strongest_basic0.05iupac2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acidaverage_mass194.1475mono_mass194.043990078smiles[H]OC(=O)C1=C([H])N([H])C2=C1C(=O)N=C(N([H])[H])N2[H]formulaC7H6N4O3inchiInChI=1S/C7H6N4O3/c8-7-10-4-3(5(12)11-7)2(1-9-4)6(13)14/h1H,(H,13,14)(H4,8,9,10,11,12)inchikeyXIUIRSLBMMTDSK-UHFFFAOYSA-Npolar_surface_area120.57refractivity47.02polarizability17.1rotatable_bond_count1acceptor_count6donor_count4physiological_charge-1formal_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::CMs1084200Specdb::EiMs3079Specdb::NmrOneD313761Specdb::NmrOneD313762Specdb::NmrOneD313763Specdb::NmrOneD313764Specdb::NmrOneD313765Specdb::NmrOneD313766Specdb::NmrOneD313767Specdb::NmrOneD313768Specdb::NmrOneD313769Specdb::NmrOneD313770Specdb::NmrOneD313771Specdb::NmrOneD313772Specdb::NmrOneD313773Specdb::NmrOneD313774Specdb::NmrOneD313775Specdb::NmrOneD313776Specdb::NmrOneD313777Specdb::NmrOneD313778Specdb::NmrOneD313779Specdb::NmrOneD313780Specdb::MsMs24710Specdb::MsMs24711Specdb::MsMs24712Specdb::MsMs31268Specdb::MsMs31269Specdb::MsMs312701334469426332127C20248611257-cyano-7-deazaguanine synthaseP77756QUEC_ECOLIqueChttp://ecmdb.ca/proteins/P77756.xml7-carboxy-7-deazaguanine synthase; queosine biosynthesisP64554queEhttp://ecmdb.ca/proteins/P64554.xmlAdenosine triphosphate + 7-Deaza-7-carboxyguanine + Ammonium > ADP + Hydrogen ion + Water + Phosphate + 7-Cyano-7-carbaguanine7-Deaza-7-carboxyguanine + Ammonia + Adenosine triphosphate > 7-Cyano-7-carbaguanine + ADP + Inorganic phosphate + Water6-Carboxy-5,6,7,8-tetrahydropterin > 7-Deaza-7-carboxyguanine + Ammonia7-Deaza-7-carboxyguanine + Ammonia + Adenosine triphosphate <> 7-Cyano-7-carbaguanine + ADP + Phosphate + WaterR09978 6-Carboxy-5,6,7,8-tetrahydropterin <> 7-Carboxy-7-carbaguanine + Ammonia + 7-Deaza-7-carboxyguanineR100027-Deaza-7-carboxyguanine + Adenosine triphosphate + Ammonium > Water + Phosphate + Adenosine diphosphate + Hydrogen ion + 7-Cyano-7-carbaguanine + ADPPW_R005180