2.02012-05-31 13:54:38 -06002015-06-03 15:54:12 -0600ECMDB01567M2MDB000422GlycineamideribotideGlycinamidoribotide conversion to N-formylglycinamide ribonucleotide is the third reaction of the de novo purine biosynthesis, a reaction catalyzed by the enzyme glycinamide ribonucleotide transformylase (EC 2.1.2.2). Glycinamide ribonucleotide (GAR) synthetase catalyzes the conversion of phosphoribosylamine, glycine, and MgATP to glycinamide ribonucleotide. (PMID: 2182115)5'-p-Ribosylglycinamide5'-p-Ribosylglycineamide5'-Phosphoribosyl-glycineamide5'-Phosphoribosylglycinamide5'-PhosphoribosylglycineamideGARGlycinamide ribonucleotideGlycineamide ribonucleotideN(1)-(5-Phospho-D-ribosyl)glycinamideN-Glycyl-5-O-phosphono-D-ribofuranosylamineN1-(5-phospho-D-ribosyl)glycinamideC7H15N2O8P286.1764286.056601978{[(2R,3S,4R,5R)-5-(2-aminoacetamido)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acidglycineamide ribonucleotide10074-18-7NCC(=O)N[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1OInChI=1S/C7H15N2O8P/c8-1-4(10)9-7-6(12)5(11)3(17-7)2-16-18(13,14)15/h3,5-7,11-12H,1-2,8H2,(H,9,10)(H2,13,14,15)/t3-,5-,6-,7-/m1/s1OBQMLSFOUZUIOB-SHUUEZRQSA-NSolidCytosollogp-2.40logs-1.29solubility1.46e+01 g/llogp-4.7pka_strongest_acidic1.23pka_strongest_basic8.14iupac{[(2R,3S,4R,5R)-5-(2-aminoacetamido)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acidaverage_mass286.1764mono_mass286.056601978smilesNCC(=O)N[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1OformulaC7H15N2O8PinchiInChI=1S/C7H15N2O8P/c8-1-4(10)9-7-6(12)5(11)3(17-7)2-16-18(13,14)15/h3,5-7,11-12H,1-2,8H2,(H,9,10)(H2,13,14,15)/t3-,5-,6-,7-/m1/s1inchikeyOBQMLSFOUZUIOB-SHUUEZRQSA-Npolar_surface_area171.57refractivity55.29polarizability23.68rotatable_bond_count5acceptor_count8donor_count6physiological_charge-1formal_charge0Purine metabolismec00230One carbon pool by folateDihydrofolic acid, a product of the folate biosynthesis pathway, can be metabolized by multiple enzymes.
Dihydrofolic acid can be reduced by a NADP-driven dihydrofolate reductase resulting in a NADPH, hydrogen ion and folic acid.
Dihydrofolic acid can also be reduced by an NADPH-driven dihydrofolate reductase resulting in a NADP and a tetrahydrofolic acid. Folic acid can also produce a tetrahydrofolic acid through a NADPH-driven dihydrofolate reductase.
Dihydrofolic acid also interacts with 5-thymidylic acid through a thymidylate synthase resulting in the release of dUMP and 5,10-methylene-THF
Tetrahydrofolic acid can be converted into 5,10-methylene-THF through two different reversible reactions.
Tetrahydrofolic acid interacts with a S-Aminomethyldihydrolipoylprotein through a aminomethyltransferase resulting in the release of ammonia, a dihydrolipoylprotein and 5,10-Methylene-THF
Tetrahydrofolic acid interacts with L-serine through a glycine hydroxymethyltransferase resulting in a glycine, water and 5,10-Methylene-THF.
The compound 5,10-methylene-THF reacts with an NADPH dependent methylenetetrahydrofolate reductase [NAD(P)H] resulting in NADP and 5-Methyltetrahydrofolic acid. This compound interacts with homocysteine through a methionine synthase resulting in L-methionine and tetrahydrofolic acid.
Tetrahydrofolic acid can be metabolized into 10-formyltetrahydrofolate through 4 different enzymes:
1.- Tetrahydrofolic acid interacts with FAICAR through a phosphoribosylaminoimidazolecarboxamide formyltransferase resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide and a 10-formyltetrahydrofolate
2.-Tetrahydrofolic acid interacts with 5'-Phosphoribosyl-N-formylglycinamide through a phosphoribosylglycinamide formyltransferase 2 resulting in a Glycineamideribotide and a 10-formyltetrahydrofolate
3.-Tetrahydrofolic acid interacts with Formic acid through a formyltetrahydrofolate hydrolase resulting in water and a 10-formyltetrahydrofolate
4.-Tetrahydrofolic acid interacts with N-formylmethionyl-tRNA(fMet) through a 10-formyltetrahydrofolate:L-methionyl-tRNA(fMet) N-formyltransferase resulting in a L-methionyl-tRNA(Met) and a 10-formyltetrahydrofolate
10-formyltetrahydrofolate can interact with a hydrogen ion through a bifunctional 5,10-methylene-tetrahydrofolate dehydrogenase resulting in water and
5,10-methenyltetrahydrofolic acid.
Tetrahydrofolic acid can be metabolized into 5,10-methenyltetrahydrofolic acid by reacting with a
5'-phosphoribosyl-a-N-formylglycineamidine through a phosphoribosylglycinamide formyltransferase 2 resulting in water, glycineamideribotide and 5,10-methenyltetrahydrofolic acid. The latter compound can either interact with water through an aminomethyltransferase resulting in a N5-Formyl-THF, or it can interact with a NADPH driven bifunctional 5,10-methylene-tetrahydrofolate dehydrogenase resulting in a NADP and 5,10-Methylene THF.
PW000773ec00670MetabolicMetabolic pathwayseco01100One Carbon Pool by Folate IDihydrofolic acid, a product of the folate biosynthesis pathway, can be metabolized by multiple enzymes.
Dihydrofolic acid can be reduced by a NADP-driven dihydrofolate reductase resulting in a NADPH, hydrogen ion and folic acid.
Dihydrofolic acid can also be reduced by an NADPH-driven dihydrofolate reductase resulting in a NADP and a tetrahydrofolic acid. Folic acid can also produce a tetrahydrofolic acid through a NADPH-driven dihydrofolate reductase.
Dihydrofolic acid also interacts with 5-thymidylic acid through a thymidylate synthase resulting in the release of dUMP and 5,10-methylene-THF
Tetrahydrofolic acid can be converted into 5,10-methylene-THF through two different reversible reactions.
Tetrahydrofolic acid interacts with a S-Aminomethyldihydrolipoylprotein through a aminomethyltransferase resulting in the release of ammonia, a dihydrolipoylprotein and 5,10-Methylene-THF
Tetrahydrofolic acid interacts with L-serine through a glycine hydroxymethyltransferase resulting in a glycine, water and 5,10-Methylene-THF.
The compound 5,10-methylene-THF reacts with an NADPH dependent methylenetetrahydrofolate reductase [NAD(P)H] resulting in NADP and 5-Methyltetrahydrofolic acid. This compound interacts with homocysteine through a methionine synthase resulting in L-methionine and tetrahydrofolic acid.
Tetrahydrofolic acid can be metabolized into 10-formyltetrahydrofolate through 4 different enzymes:
1.- Tetrahydrofolic acid interacts with FAICAR through a phosphoribosylaminoimidazolecarboxamide formyltransferase resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide and a 10-formyltetrahydrofolate
2.-Tetrahydrofolic acid interacts with 5'-Phosphoribosyl-N-formylglycinamide through a phosphoribosylglycinamide formyltransferase 2 resulting in a Glycineamideribotide and a 10-formyltetrahydrofolate
3.-Tetrahydrofolic acid interacts with Formic acid through a formyltetrahydrofolate hydrolase resulting in water and a 10-formyltetrahydrofolate
4.-Tetrahydrofolic acid interacts with N-formylmethionyl-tRNA(fMet) through a 10-formyltetrahydrofolate:L-methionyl-tRNA(fMet) N-formyltransferase resulting in a L-methionyl-tRNA(Met) and a 10-formyltetrahydrofolate
10-formyltetrahydrofolate can interact with a hydrogen ion through a bifunctional 5,10-methylene-tetrahydrofolate dehydrogenase resulting in water and
5,10-methenyltetrahydrofolic acid.
Tetrahydrofolic acid can be metabolized into 5,10-methenyltetrahydrofolic acid by reacting with a
5'-phosphoribosyl-a-N-formylglycineamidine through a phosphoribosylglycinamide formyltransferase 2 resulting in water, glycineamideribotide and 5,10-methenyltetrahydrofolic acid. The latter compound can either interact with water through an aminomethyltransferase resulting in a N5-Formyl-THF, or it can interact with a NADPH driven bifunctional 5,10-methylene-tetrahydrofolate dehydrogenase resulting in a NADP and 5,10-Methylene THF.
PW001735Metabolicsuperpathway of 5-aminoimidazole ribonucleotide biosynthesisPWY-62775-aminoimidazole ribonucleotide biosynthesis IPWY-61215-aminoimidazole ribonucleotide biosynthesis IIPWY-6122tetrahydrofolate salvage from 5,10-methenyltetrahydrofolatePWY-6613Specdb::CMs2935Specdb::CMs38227Specdb::CMs148298Specdb::NmrOneD148780Specdb::NmrOneD148781Specdb::NmrOneD148782Specdb::NmrOneD148783Specdb::NmrOneD148784Specdb::NmrOneD148785Specdb::NmrOneD148786Specdb::NmrOneD148787Specdb::NmrOneD148788Specdb::NmrOneD148789Specdb::NmrOneD148790Specdb::NmrOneD148791Specdb::NmrOneD148792Specdb::NmrOneD148793Specdb::NmrOneD148794Specdb::NmrOneD148795Specdb::NmrOneD148796Specdb::NmrOneD148797Specdb::NmrOneD148798Specdb::NmrOneD148799Specdb::MsMs29540Specdb::MsMs29541Specdb::MsMs29542Specdb::MsMs36098Specdb::MsMs36099Specdb::MsMs36100Specdb::MsMs2703398Specdb::MsMs2703399Specdb::MsMs2703400Specdb::MsMs3002740Specdb::MsMs3002741Specdb::MsMs3002742HMDB02022440137141370C03838183495-PHOSPHO-RIBOSYL-GLYCINEAMIDEGARKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Caperelli CA, Giroux EL: The human glycinamide ribonucleotide transformylase domain: purification, characterization, and kinetic mechanism. Arch Biochem Biophys. 1997 May 1;341(1):98-103.9143358McKerns KW: Gonadotropin regulation of nucleotide biosynthesis in corpus luteum. Biochemistry. 1973 Dec 4;12(25):5206-11.4366083Phosphoribosylglycinamide formyltransferaseP08179PUR3_ECOLIpurNhttp://ecmdb.ca/proteins/P08179.xmlPhosphoribosylamine--glycine ligaseP15640PUR2_ECOLIpurDhttp://ecmdb.ca/proteins/P15640.xmlPhosphoribosylglycinamide formyltransferase 2P33221PURT_ECOLIpurThttp://ecmdb.ca/proteins/P33221.xmlAdenosine triphosphate + Formic acid + Glycineamideribotide > ADP + 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + PhosphateGARTRANSFORMYL2-RXNN10-Formyl-THF + Glycineamideribotide <> 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acidR04325GART-RXNAdenosine triphosphate + Glycine + 5-Phosphoribosylamine <> ADP + Glycineamideribotide + Hydrogen ion + PhosphateR04144GLYRIBONUCSYN-RXNAdenosine triphosphate + 5-Phosphoribosylamine + Glycine <> ADP + Phosphate + GlycineamideribotideR04144N10-Formyl-THF + Glycineamideribotide <> Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamideR04325Glycineamideribotide + 5,10-Methenyltetrahydrofolate + Water <> 5'-Phosphoribosyl-N-formylglycineamide + Tetrahydrofolic acidR04326Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide > Water + 5,10-Methenyltetrahydrofolic acid + Glycineamideribotide + GlycineamideribotidePW_R002546Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide > 10-Formyltetrahydrofolate + Glycineamideribotide + N10-Formyl-THF + GlycineamideribotidePW_R0025475'-phosphoribosyl-a-N-formylglycineamidine + Tetrahydrofolic acid + Tetrahydrofolic acid > Water + Glycineamideribotide + 5,10-Methenyltetrahydrofolic acid + GlycineamideribotidePW_R002550N10-Formyl-THF + Glycineamideribotide <>5 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acidAdenosine triphosphate + Glycine + 5 5-Phosphoribosylamine <> ADP + Glycineamideribotide + Hydrogen ion + PhosphateN10-Formyl-THF + Glycineamideribotide <>5 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid