2.0 2012-05-31 10:25:26 -0600 2015-06-03 15:53:26 -0600 ECMDB00280 M2MDB000115 Phosphoribosyl pyrophosphate Phosphoribosyl pyrophosphate (PRPP) is a pentosephosphate. The key substance in the biosynthesis of histidine, tryptophan, and purine and pyrimidine nucleotides. It is formed from ribose 5-phosphate by the enzyme ribose-phosphate diphosphokinase. It plays a role in transferring phosphate groups in several reactions. (Wikipedia) &alpha;-D-5-P-RibosylPP &alpha;-D-5-phosphoribosylPP 5-phospho-a-D-Ribose 1-diphosphate 5-phospho-a-D-Ribose 1-diphosphoric acid 5-Phospho-a-D-ribose-1-diphosphate 5-phospho-a-D-Ribose-1-diphosphoric acid 5-Phospho-a-D-ribosyl pyrophosphate 5-phospho-a-D-Ribosyl pyrophosphoric acid 5-phospho-a-D-Riobse 1-diphosphate 5-phospho-a-D-Riobse 1-diphosphoric acid 5-phospho-a-delta-Ribose 1-diphosphate 5-phospho-a-delta-Ribose 1-diphosphoric acid 5-phospho-a-delta-Ribose-1-diphosphate 5-phospho-a-delta-Ribose-1-diphosphoric acid 5-phospho-a-delta-Ribosyl pyrophosphate 5-phospho-a-delta-Ribosyl pyrophosphoric acid 5-phospho-a-δ-Ribose 1-diphosphate 5-phospho-a-δ-Ribose 1-diphosphoric acid 5-phospho-a-δ-Ribose-1-diphosphate 5-phospho-a-δ-Ribose-1-diphosphoric acid 5-phospho-a-δ-Ribosyl pyrophosphate 5-phospho-a-δ-Ribosyl pyrophosphoric acid 5-Phospho-alpha-D-ribose 1-diphosphate 5-phospho-alpha-D-Ribose 1-diphosphoric acid 5-Phospho-alpha-D-ribose-1-diphosphate 5-phospho-alpha-D-Ribose-1-diphosphoric acid 5-Phospho-alpha-D-ribosyl pyrophosphate 5-phospho-alpha-D-Ribosyl pyrophosphoric acid 5-Phospho-alpha-D-riobse 1-diphosphate 5-phospho-alpha-D-Riobse 1-diphosphoric acid 5-Phospho-alpha-delta-ribose 1-diphosphate 5-phospho-alpha-delta-Ribose 1-diphosphoric acid 5-Phospho-alpha-delta-ribose-1-diphosphate 5-phospho-alpha-delta-Ribose-1-diphosphoric acid 5-Phospho-alpha-delta-ribosyl pyrophosphate 5-phospho-alpha-delta-Ribosyl pyrophosphoric acid 5-Phospho-ribosyl-pyrophosphate 5-phospho-Ribosyl-pyrophosphoric acid 5-phospho-α-D-Ribose 1-diphosphate 5-phospho-α-D-Ribose 1-diphosphoric acid 5-phospho-α-D-Ribose-1-diphosphate 5-phospho-α-D-Ribose-1-diphosphoric acid 5-phospho-α-D-Ribosyl pyrophosphate 5-phospho-α-D-Ribosyl pyrophosphoric acid 5-phospho-α-D-Riobse 1-diphosphate 5-phospho-α-D-Riobse 1-diphosphoric acid 5-phospho-α-δ-Ribose 1-diphosphate 5-phospho-α-δ-Ribose 1-diphosphoric acid 5-phospho-α-δ-Ribose-1-diphosphate 5-phospho-α-δ-Ribose-1-diphosphoric acid 5-phospho-α-δ-Ribosyl pyrophosphate 5-phospho-α-δ-Ribosyl pyrophosphoric acid 5-Phosphoribose 1-pyrophosphate 5-Phosphoribose 1-pyrophosphoric acid 5-Phosphoribosyl 1-diphosphate 5-Phosphoribosyl 1-diphosphoric acid 5-Phosphoribosyl 1-pyrophosphate 5-Phosphoribosyl 1-pyrophosphoric acid 5-Phosphoribosyl a-1-pyrophosphate 5-Phosphoribosyl a-1-pyrophosphoric acid 5-Phosphoribosyl diphosphate 5-Phosphoribosyl diphosphoric acid 5-Phosphoribosyl-1-PP 5-Phosphoribosyl-1-pyrophosphate 5-Phosphoribosyl-1-pyrophosphoric acid 5-Phosphoribosyl-PP 5-Phosphoribosylpyrophosphate 5-Phosphoribosylpyrophosphoric acid 5-Phosphorylribose 1-a-diphosphate 5-Phosphorylribose 1-a-diphosphoric acid 5-Phosphorylribose 1-alpha-diphosphate 5-Phosphorylribose 1-alpha-diphosphoric acid 5-Phosphorylribose 1-pyrophosphate 5-Phosphorylribose 1-pyrophosphoric acid 5-Phosphorylribose 1-α-diphosphate 5-Phosphorylribose 1-α-diphosphoric acid 5-Phosphorylribosyl 1-pyrophosphate 5-Phosphorylribosyl 1-pyrophosphoric acid A-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose a-D-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose a-D-5-P-RibosylPP A-D-5-Phosphoribosyl 1-pyrophosphate a-D-5-Phosphoribosyl 1-pyrophosphoric acid a-D-5-PhosphoribosylPP A-D-Ribofuranose 5-phosphate 1-pyrophosphate a-D-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid A-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate) a-D-Ribofuranose, 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid) a-delta-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose a-delta-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose a-delta-5-Phosphoribosyl 1-pyrophosphate a-delta-5-Phosphoribosyl 1-pyrophosphoric acid a-delta-Ribofuranose 5-phosphate 1-pyrophosphate a-delta-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid a-δ-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose a-δ-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose a-δ-5-Phosphoribosyl 1-pyrophosphate a-δ-5-Phosphoribosyl 1-pyrophosphoric acid a-δ-Ribofuranose 5-phosphate 1-pyrophosphate a-δ-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid Alpha-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose alpha-D-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose Alpha-D-5-P-RibosylPP Alpha-D-5-Phosphoribosyl 1-pyrophosphate alpha-D-5-Phosphoribosyl 1-pyrophosphoric acid Alpha-D-5-PhosphoribosylPP Alpha-D-Ribofuranose 5-phosphate 1-pyrophosphate alpha-D-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid Alpha-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate) alpha-D-Ribofuranose, 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid) Alpha-delta-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) Ribofuranose alpha-delta-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose Alpha-delta-5-Phosphoribosyl 1-pyrophosphate alpha-delta-5-Phosphoribosyl 1-pyrophosphoric acid Alpha-delta-Ribofuranose 5-phosphate 1-pyrophosphate alpha-delta-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid Phosphoribosyl pyrophosphate Phosphoribosyl pyrophosphoric acid Phosphoribosyl-1-pyrophosphate Phosphoribosyl-1-pyrophosphoric acid Phosphoribosyl-pyrophosphate Phosphoribosyl-pyrophosphoric acid Phosphoribosylpyrophosphate Phosphoribosylpyrophosphorate Phosphoribosylpyrophosphoric acid PP-Ribose-P PRib-PP PRPP α-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose α-D-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose α-D-5-P-RibosylPP α-D-5-Phosphoribosyl 1-pyrophosphate α-D-5-Phosphoribosyl 1-pyrophosphoric acid α-D-5-PhosphoribosylPP α-D-Ribofuranose 5-phosphate 1-pyrophosphate α-D-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid α-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate) α-D-Ribofuranose, 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid) α-δ-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose α-δ-5-(Dihydrogen phosphoric acid) 1-(trihydrogen pyrophosphoric acid) ribofuranose α-δ-5-Phosphoribosyl 1-pyrophosphate α-δ-5-Phosphoribosyl 1-pyrophosphoric acid α-δ-Ribofuranose 5-phosphate 1-pyrophosphate α-δ-Ribofuranose 5-phosphoric acid 1-pyrophosphoric acid C5H13O14P3 390.0696 389.95181466 [({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid phosphoribosylpyrophosphate 7540-64-9 O[C@H]1[C@@H](O)[C@@H](O[P@](O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O InChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1 PQGCEDQWHSBAJP-TXICZTDVSA-N Solid Cytosol logp -0.74 ALOGPS logs -1.53 ALOGPS solubility 1.16e+01 g/l ALOGPS logp -3 ChemAxon pka_strongest_acidic 1.09 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac [({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid ChemAxon average_mass 390.0696 ChemAxon mono_mass 389.95181466 ChemAxon smiles O[C@H]1[C@@H](O)[C@@H](O[P@](O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O ChemAxon formula C5H13O14P3 ChemAxon inchi InChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1 ChemAxon inchikey PQGCEDQWHSBAJP-TXICZTDVSA-N ChemAxon polar_surface_area 229.74 ChemAxon refractivity 62.58 ChemAxon polarizability 27.46 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 11 ChemAxon donor_count 7 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Alanine, aspartate and glutamate metabolism ec00250 Purine metabolism ec00230 Pyrimidine metabolism The metabolism of pyrimidines begins with L-glutamine interacting with water molecule and a hydrogen carbonate through an ATP driven carbamoyl phosphate synthetase resulting in a hydrogen ion, an ADP, a phosphate, an L-glutamic acid and a carbamoyl phosphate. The latter compound interacts with an L-aspartic acid through a aspartate transcarbamylase resulting in a phosphate, a hydrogen ion and a N-carbamoyl-L-aspartate. The latter compound interacts with a hydrogen ion through a dihydroorotase resulting in the release of a water molecule and a 4,5-dihydroorotic acid. This compound interacts with an ubiquinone-1 through a dihydroorotate dehydrogenase, type 2 resulting in a release of an ubiquinol-1 and an orotic acid. The orotic acid then interacts with a phosphoribosyl pyrophosphate through a orotate phosphoribosyltransferase resulting in a pyrophosphate and an orotidylic acid. The latter compound then interacts with a hydrogen ion through an orotidine-5 '-phosphate decarboxylase, resulting in an release of carbon dioxide and an Uridine 5' monophosphate. The Uridine 5' monophosphate process to get phosphorylated by an ATP driven UMP kinase resulting in the release of an ADP and an Uridine 5--diphosphate. Uridine 5-diphosphate can be metabolized in multiple ways in order to produce a Deoxyuridine triphosphate. 1.-Uridine 5-diphosphate interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in the release of a water molecule and an oxidized thioredoxin and an dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate. 2.-Uridine 5-diphosphate interacts with a reduced NrdH glutaredoxin-like protein through a Ribonucleoside-diphosphate reductase 1 resulting in a release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate. 3.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate. The latter compound interacts with a reduced flavodoxin through ribonucleoside-triphosphate reductase resulting in the release of an oxidized flavodoxin, a water molecule and a Deoxyuridine triphosphate 4.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in the release of a water molecule, an oxidized flavodoxin and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. 5.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP then interacts with a reduced NrdH glutaredoxin-like protein through a ribonucleoside-diphosphate reductase 2 resulting in the release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. 6.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. The deoxyuridine triphosphate then interacts with a water molecule through a nucleoside triphosphate pyrophosphohydrolase resulting in a release of a hydrogen ion, a phosphate and a dUMP. The dUMP then interacts with a methenyltetrahydrofolate through a thymidylate synthase resulting in a dihydrofolic acid and a 5-thymidylic acid. Then 5-thymidylic acid is then phosphorylated through a nucleoside diphosphate kinase resulting in the release of an ADP and thymidine 5'-triphosphate. PW000942 ec00240 Metabolic Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Tryptophan metabolism The biosynthesis of L-tryptophan begins with L-glutamine interacting with a chorismate through a anthranilate synthase which results in a L-glutamic acid, a pyruvic acid, a hydrogen ion and a 2-aminobenzoic acid. The aminobenzoic acid interacts with a phosphoribosyl pyrophosphate through an anthranilate synthase component II resulting in a pyrophosphate and a N-(5-phosphoribosyl)-anthranilate. The latter compound is then metabolized by an indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in a 1-(o-carboxyphenylamino)-1-deoxyribulose 5'-phosphate. This compound then interacts with a hydrogen ion through a indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in the release of carbon dioxide, a water molecule and a (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate. The latter compound then interacts with a D-glyceraldehyde 3-phosphate and an Indole. The indole interacts with an L-serine through a tryptophan synthase, β subunit dimer resulting in a water molecule and an L-tryptophan. The metabolism of L-tryptophan starts with L-tryptophan being dehydrogenated by a tryptophanase / L-cysteine desulfhydrase resulting in the release of a hydrogen ion, an Indole and a 2-aminoacrylic acid. The latter compound is isomerized into a 2-iminopropanoate. This compound then interacts with a water molecule and a hydrogen ion spontaneously resulting in the release of an Ammonium and a pyruvic acid. The pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an Acetyl-CoA PW000815 ec00380 Metabolic Drug metabolism - other enzymes ec00983 Histidine metabolism ec00340 Nicotinate and nicotinamide metabolism ec00760 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 NAD biosynthesis Nicotinamide adenine dinucleotide (NAD) can be biosynthesized from L-aspartic acid.This amino acid reacts with oxygen through an L-aspartate oxidase resulting in a hydrogen ion, hydrogen peroxide and an iminoaspartic acid. The latter compound interacts with dihydroxyacetone phosphate through a quinolinate synthase A, resulting in a phosphate, water, and a quinolic acid. Quinolic acid interacts with phosphoribosyl pyrophosphate and hydrogen ion through a quinolinate phosphoribosyltransferase resulting in pyrophosphate, carbon dioxide and nicotinate beta-D-ribonucleotide. This last compound is adenylated through an ATP driven nicotinate-mononucleotide adenylyltransferase releasing a pyrophosphate and resulting in a nicotinic acid adenine dinucleotide. Nicotinic acid adenine dinucleotide is processed through an NAD synthetase, NH3-dependent in two different manners. In the first case, Nicotinic acid adenine dinucleotide interacts with ATP, L-glutamine and water through the enzyme and results in hydrogen ion, AMP, pyrophosphate, L-glutamic acid and NAD. In the second case, Nicotinic acid adenine dinucleotide interacts with ATP and ammonium through the enzyme resulting in a pyrophosphate, AMP, hydrogen ion and NAD. NAD then proceeds to regulate its own pathway by repressing L-aspartate oxidase. As a general rule, most prokaryotes utilize the aspartate de novo pathway, in which the nicotinate moiety of NAD is synthesized from aspartate , while in eukaryotes, the de novo pathway starts with tryptophan. PW000829 Metabolic NAD salvage Even though NAD molecules are not consumed during oxidation reactions, they have a relatively short half-life. For example, in E. coli the NAD+ half-life is 90 minutes. Once enzymatically degraded, the pyrimidine moiety of the molecule can be recouped via the NAD salvage cycles. This pathway is used for two purposes: it recycles the internally degraded NAD products nicotinamide D-ribonucleotide (also known as nicotinamide mononucleotide, or NMN) and nicotinamide, and it is used for the assimilation of exogenous NAD+. NAD reacts spontaneously with water resulting in the release of hydrogen ion, AMP and beta-nicotinamide D-ribonucleotide. This enzyme can either interact spontaneously with water resulting in the release of D-ribofuranose 5-phosphate, hydrogen ion and Nacinamide. On the other hand beta-nicotinamide D-ribonucleotide can also react with water through NMN amidohydrolase resulting in ammonium, and Nicotinate beta-D-ribonucleotide. Also it can interact with water spontaneously resulting in the release of phosphate resulting in a Nicotinamide riboside. Niacinamide interacts with water through a nicotinamidase resulting in a release of ammonium and nicotinic acid. This compound interacts with water and phosphoribosyl pyrophosphate through an ATP driven nicotinate phosphoribosyltransferase resulting in the release of ADP, pyrophosphate and phosphate and nicotinate beta-D-ribonucleotide. Nicotinamide riboside interacts with an ATP driven NadR DNA-binding transcriptional repressor and NMN adenylyltransferase (Escherichia coli) resulting in a ADP, hydrogen ion and beta-nicotinamide D-ribonucleotide. This compound interacts with ATP and hydrogen ion through NadR DNA-binding transcriptional repressor and NMN adenylyltransferase resulting in pyrophosphate and NAD. Nicotinate beta-D-ribonucleotide is adenylated through the interaction with ATP and a hydrogen ion through a nicotinate-mononucleotide adenylyltransferase resulting in pyrophosphate and Nicotinic acid adenine dinucleotide. Nicotinic acid adenine dinucleotide interacts with L-glutamine and water through an ATP driven NAD synthetase, NH3-dependent resulting in AMP, pyrophosphate, hydrogen ion, L-glutamic acid and NAD. PW000830 Metabolic PRPP Biosynthesis The biosynthesis of phosphoribosyl pyrophosphate begins with a product of the pentose phosphate, D-ribose 5-phosphate interact with a phosphopentomutase resulting in a Ribose 1-phosphate or it can be phosphorylated through an ATP driven ribose-phosphate diphosphokinase resulting in a release of a hydrogen ion, an AMP and a phosphoribosyl pyrophosphate. The latter compound is then involved in the purine nucleotides de novo biosynthesis pathway. Ribose 1-phosphate can interact spontaneously with ATP resulting in a release of hydrogen ion, ADP and a ribose 1,5-biphosphate. The latter compound is then phosphorylated through a ribose 1,5-bisphosphokinase resulting in the release of ADP and phosphoribosyl pyrophosphate. The latter compound is then involved in the purine nucleotides de novo biosynthesis pathway. PW000909 Metabolic Secondary Metabolites: Histidine biosynthesis Histidine biosynthesis starts with a product of PRPP biosynthesis pathway, phosphoribosyl pyrophosphate which interacts with a hydrogen ion through an ATP phosphoribosyltransferase resulting in an pyrophosphate and a phosphoribosyl-ATP. This compound interacts with water through a phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase resulting in the release of pyrophosphate, hydrogen ion and a phosphoribosyl-AMP. This enzyme proceeds to interact with phosphoribosyl-AMP and water resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide. This compound is then isomerized by a N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase resulting in a PhosphoribosylformiminoAICAR-phosphate. This compound reacts with L-glutamine through an imidazole glycerol phosphate synthase resulting in a L-glutamic acid, hydrogen ion, 5-aminoimidazole-4-carboxamide and a D-erythro-imidazole-glycerol-phosphate. This compound reacts with a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase, dehydrating the compound and resulting in a imidazole acetol-phosphate. This compound interacts with L-glutamic acid through a histidinol-phosphate aminotransferase, releasing oxoglutaric acid and L-histidinol-phosphate. The latter compound interacts with water and a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase resulting in L-histidinol and phosphate. L-histidinol interacts with a NAD-driven histidinol dehydrogenase resulting in a Histidinal. This in turn reacts with water in a NAD driven histidinal dehydrogenase resulting in L-Histidine. L-Histidine then represses ATP phosphoribosyltransferase, regulation its own biosynthesis. PW000984 Metabolic histidine biosynthesis Histidine biosynthesis starts with a product of PRPP biosynthesis pathway, phosphoribosyl pyrophosphate which interacts with a hydrogen ion through an ATP phosphoribosyltransferase resulting in an pyrophosphate and a phosphoribosyl-ATP. This compound interacts with water through a phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase resulting in the release of pyrophosphate, hydrogen ion and a phosphoribosyl-AMP. This enzyme proceeds to interact with phosphoribosyl-AMP and water resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide. This compound is then isomerized by a N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase resulting in a PhosphoribosylformiminoAICAR-phosphate. This compound reacts with L-glutamine through an imidazole glycerol phosphate synthase resulting in a L-glutamic acid, hydrogen ion, 5-aminoimidazole-4-carboxamide and a D-erythro-imidazole-glycerol-phosphate. This compound reacts with a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase, dehydrating the compound and resulting in a imidazole acetol-phosphate. This compound interacts with L-glutamic acid through a histidinol-phosphate aminotransferase, releasing oxoglutaric acid and L-histidinol-phosphate. The latter compound interacts with water and a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase resulting in L-histidinol and phosphate. L-histidinol interacts with a NAD-driven histidinol dehydrogenase resulting in a Histidinal. This in turn reacts with water in a NAD driven histidinal dehydrogenase resulting in L-Histidine. L-Histidine then represses ATP phosphoribosyltransferase, regulation its own biosynthesis. PW000810 Metabolic purine nucleotides de novo biosynthesis The biosynthesis of purine nucleotides is a complex process that begins with a phosphoribosyl pyrophosphate. This compound interacts with water and L-glutamine through a amidophosphoribosyl transferase resulting in a pyrophosphate, L-glutamic acid and a 5-phosphoribosylamine. The latter compound proceeds to interact with a glycine through an ATP driven phosphoribosylamine-glycine ligase resulting in the addition of glycine to the compound. This reaction releases an ADP, a phosphate, a hydrogen ion and a N1-(5-phospho-β-D-ribosyl)glycinamide. The latter compound interacts with formic acid, through an ATP driven phosphoribosylglycinamide formyltransferase 2 resulting in a phosphate, an ADP, a hydrogen ion and a 5-phosphoribosyl-N-formylglycinamide. The latter compound interacts with L-glutamine, and water through an ATP-driven phosphoribosylformylglycinamide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion, a L-glutamic acid and a 2-(formamido)-N1-(5-phospho-D-ribosyl)acetamidine. The latter compound interacts with an ATP driven phosphoribosylformylglycinamide cyclo-ligase resulting in a release of ADP, a phosphate, a hydrogen ion and a 5-aminoimidazole ribonucleotide. The latter compound interacts with a hydrogen carbonate through an ATP driven N5-carboxyaminoimidazole ribonucleotide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion and a N5-carboxyaminoimidazole ribonucleotide.The latter compound then interacts with a N5-carboxyaminoimidazole ribonucleotide mutase resulting in a 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate. This compound interacts with an L-aspartic acid through an ATP driven phosphoribosylaminoimidazole-succinocarboxamide synthase resulting in a phosphate, an ADP, a hydrogen ion and a SAICAR. SAICAR interacts with an adenylosuccinate lyase resulting in a fumaric acid and an AICAR. AICAR interacts with a formyltetrahydrofolate through a AICAR transformylase / IMP cyclohydrolase resulting in a release of a tetrahydropterol mono-l-glutamate and a FAICAR. The latter compound, FAICAR, interacts in a reversible reaction through a AICAR transformylase / IMP cyclohydrolase resulting in a release of water and Inosinic acid. Inosinic acid can be metabolized to produce dGTP and dATP three different methods each. dGTP: Inosinic acid, water and NAD are processed by IMP dehydrogenase resulting in a release of NADH, a hydrogen ion and Xanthylic acid. Xanthylic acid interacts with L-glutamine, and water through an ATP driven GMP synthetase resulting in pyrophosphate, AMP, L-glutamic acid, a hydrogen ion and Guanosine monophosphate. The latter compound is the phosphorylated by reacting with an ATP driven guanylate kinase resulting in a release of ADP and a Gaunosine diphosphate. Guanosine diphosphate can be metabolized in three different ways: 1.-Guanosine diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and a Guanosine triphosphate. This compound interacts with a reduced flavodoxin protein through a ribonucleoside-triphosphate reductase resulting in a oxidized flavodoxin a water moleculer and a dGTP 2.-Guanosine diphosphate interacts with a reduced NrdH glutaredoxin-like proteins through a ribonucleoside-diphosphate reductase 2 resulting in the release of an oxidized NrdH glutaredoxin-like protein, a water molecule and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP. 3.-Guanosine diphosphate interacts with a reduced thioredoxin ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP. dATP: Inosinic acid interacts with L-aspartic acid through an GTP driven adenylosuccinate synthase results in the release of GDP, a hydrogen ion, a phosphate and N(6)-(1,2-dicarboxyethyl)AMP. The latter compound is then cleaved by a adenylosuccinate lyase resulting in a fumaric acid and an Adenosine monophosphate. This compound is then phosphorylated by an adenylate kinase resulting in the release of ATP and an adenosine diphosphate. Adenosine diphosphate can be metabolized in three different ways: 1.-Adenosine diphosphate is involved in a reversible reaction by interacting with a hydrogen ion and a phosphate through a ATP synthase / thiamin triphosphate synthase resulting in a hydrogen ion, a water molecule and an Adenosine triphosphate. The adenosine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in an oxidized flavodoxin, a water molecule and a dATP 2.- Adenosine diphosphate interacts with an reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, a oxidized thioredoxin and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP 3.- Adenosine diphosphate interacts with an reduced NrdH glutaredoxin-like protein through a ribonucleoside diphosphate reductase 2 resulting in a release of a water molecule, a oxidized glutaredoxin-like protein and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP PW000910 Metabolic purine nucleotides de novo biosynthesis 1435709748 PW000960 Metabolic tryptophan metabolism II The biosynthesis of L-tryptophan begins with L-glutamine interacting with a chorismate through a anthranilate synthase which results in a L-glutamic acid, a pyruvic acid, a hydrogen ion and a 2-aminobenzoic acid. The aminobenzoic acid interacts with a phosphoribosyl pyrophosphate through an anthranilate synthase component II resulting in a pyrophosphate and a N-(5-phosphoribosyl)-anthranilate. The latter compound is then metabolized by an indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in a 1-(o-carboxyphenylamino)-1-deoxyribulose 5'-phosphate. This compound then interacts with a hydrogen ion through a indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in the release of carbon dioxide, a water molecule and a (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate. The latter compound then interacts with a D-glyceraldehyde 3-phosphate and an Indole. The indole interacts with an L-serine through a tryptophan synthase, β subunit dimer resulting in a water molecule and an L-tryptophan. The metabolism of L-tryptophan starts with L-tryptophan being dehydrogenated by a tryptophanase / L-cysteine desulfhydrase resulting in the release of a hydrogen ion, an Indole and a 2-aminoacrylic acid. The latter compound is isomerized into a 2-iminopropanoate. This compound then interacts with a water molecule and a hydrogen ion spontaneously resulting in the release of an Ammonium and a pyruvic acid. The pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an Acetyl-CoA PW001916 Metabolic Thiamin diphosphate biosynthesis PW002028 Metabolic adenine and adenosine salvage I The salvage of adenine begins with adenine being transporter into the cytosol through a adeP hydrogen symporter. Once in the cytosol adenine is degraded by reacting with a ribose-1-phosphate through an adenosine phosphorylase resulting in the release of a phosphate and adenosine. Adenosine is then deaminated by reacting with water, a hydrogen ion and an adenosine deaminase resulting in the release of an ammonium and a inosine . Inosine then reacts with a phosphate through a inosine phosphorylase resulting in the release of a ribose 1-phosphate and a hypoxanthine. Hypoxanthine reacts with a PRPP through a hypoxanthine phosphoribosyltransferase resulting in the release of a pyrophosphate and a IMP molecule. PW002069 Metabolic adenine and adenosine salvage III Adenosine is first incorporated into the cytosol through either a nupG or a nupC transporter. Once in the cytosol, adenosine is degraded into adenine by reacting with a water and a adenosine nucleosidase, releasing a D-ribofuranose and a adenine. The adenine then reacts with a PRPP through a adenine phosphoribosyltransferase resulting in the release of a pyrophosphate and an AMP PW002072 Metabolic guanine and guanosine salvage Guanosine 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 PW002074 Metabolic purine nucleotides de novo biosynthesis 2 The biosynthesis of purine nucleotides is a complex process that begins with a phosphoribosyl pyrophosphate. This compound interacts with water and L-glutamine through a amidophosphoribosyl transferase resulting in a pyrophosphate, L-glutamic acid and a 5-phosphoribosylamine. The latter compound proceeds to interact with a glycine through an ATP driven phosphoribosylamine-glycine ligase resulting in the addition of glycine to the compound. This reaction releases an ADP, a phosphate, a hydrogen ion and a N1-(5-phospho-β-D-ribosyl)glycinamide. The latter compound interacts with formic acid, through an ATP driven phosphoribosylglycinamide formyltransferase 2 resulting in a phosphate, an ADP, a hydrogen ion and a 5-phosphoribosyl-N-formylglycinamide. The latter compound interacts with L-glutamine, and water through an ATP-driven phosphoribosylformylglycinamide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion, a L-glutamic acid and a 2-(formamido)-N1-(5-phospho-D-ribosyl)acetamidine. The latter compound interacts with an ATP driven phosphoribosylformylglycinamide cyclo-ligase resulting in a release of ADP, a phosphate, a hydrogen ion and a 5-aminoimidazole ribonucleotide. The latter compound interacts with a hydrogen carbonate through an ATP driven N5-carboxyaminoimidazole ribonucleotide synthetase resulting in a release of a phosphate, an ADP, a hydrogen ion and a N5-carboxyaminoimidazole ribonucleotide(5-Phosphoribosyl-5-carboxyaminoimidazole).The latter compound then interacts with a N5-carboxyaminoimidazole ribonucleotide mutase resulting in a 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate. This compound interacts with an L-aspartic acid through an ATP driven phosphoribosylaminoimidazole-succinocarboxamide synthase resulting in a phosphate, an ADP, a hydrogen ion and a SAICAR. SAICAR interacts with an adenylosuccinate lyase resulting in a fumaric acid and an AICAR. AICAR interacts with a formyltetrahydrofolate through a AICAR transformylase / IMP cyclohydrolase resulting in a release of a tetrahydropterol mono-l-glutamate and a FAICAR. The latter compound, FAICAR, interacts in a reversible reaction through a AICAR transformylase / IMP cyclohydrolase resulting in a release of water and Inosinic acid. Inosinic acid can be metabolized to produce dGTP and dATP three different methods each. dGTP: Inosinic acid, water and NAD are processed by IMP dehydrogenase resulting in a release of NADH, a hydrogen ion and Xanthylic acid. Xanthylic acid interacts with L-glutamine, and water through an ATP driven GMP synthetase resulting in pyrophosphate, AMP, L-glutamic acid, a hydrogen ion and Guanosine monophosphate. The latter compound is the phosphorylated by reacting with an ATP driven guanylate kinase resulting in a release of ADP and a Gaunosine diphosphate. Guanosine diphosphate can be metabolized in three different ways: 1.-Guanosine diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and a Guanosine triphosphate. This compound interacts with a reduced flavodoxin protein through a ribonucleoside-triphosphate reductase resulting in a oxidized flavodoxin a water moleculer and a dGTP 2.-Guanosine diphosphate interacts with a reduced NrdH glutaredoxin-like proteins through a ribonucleoside-diphosphate reductase 2 resulting in the release of an oxidized NrdH glutaredoxin-like protein, a water molecule and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP. 3.-Guanosine diphosphate interacts with a reduced thioredoxin ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dGDP. The dGDP is then phosphorylated by interacting with an ATP-driven nucleoside diphosphate kinase resulting in an ADP and dGTP. dATP: Inosinic acid interacts with L-aspartic acid through an GTP driven adenylosuccinate synthase results in the release of GDP, a hydrogen ion, a phosphate and N(6)-(1,2-dicarboxyethyl)AMP. The latter compound is then cleaved by a adenylosuccinate lyase resulting in a fumaric acid and an Adenosine monophosphate. This compound is then phosphorylated by an adenylate kinase resulting in the release of ATP and an adenosine diphosphate. Adenosine diphosphate can be metabolized in three different ways: 1.-Adenosine diphosphate is involved in a reversible reaction by interacting with a hydrogen ion and a phosphate through a ATP synthase / thiamin triphosphate synthase resulting in a hydrogen ion, a water molecule and an Adenosine triphosphate. The adenosine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in an oxidized flavodoxin, a water molecule and a dATP 2.- Adenosine diphosphate interacts with an reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, a oxidized thioredoxin and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP 3.- Adenosine diphosphate interacts with an reduced NrdH glutaredoxin-like protein through a ribonucleoside diphosphate reductase 2 resulting in a release of a water molecule, a oxidized glutaredoxin-like protein and a dADP. The dADP is then phosphorylated by a nucleoside diphosphate kinase resulting in the release of ADP and a dATP PW002033 Metabolic purine ribonucleosides degradation Purine 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. PW002076 Metabolic adenine and adenosine salvage III PWY-6609 adenine and adenosine salvage II PWY-6605 PRPP biosynthesis I PWY0-662 NAD salvage pathway I PYRIDNUCSAL-PWY NAD biosynthesis I (from aspartate) PYRIDNUCSYN-PWY salvage pathways of pyrimidine ribonucleotides PWY0-163 superpathway of 5-aminoimidazole ribonucleotide biosynthesis PWY-6277 5-aminoimidazole ribonucleotide biosynthesis I PWY-6121 5-aminoimidazole ribonucleotide biosynthesis II PWY-6122 guanine and guanosine salvage I PWY-6620 uridine-5'-phosphate biosynthesis PWY-5686 histidine biosynthesis HISTSYN-PWY tryptophan biosynthesis TRPSYN-PWY xanthine and xanthosine salvage SALVPURINE2-PWY PRPP biosynthesis II PWY0-661 Specdb::CMs 2740 Specdb::CMs 37400 Specdb::CMs 163468 Specdb::CMs 1056651 Specdb::CMs 1056653 Specdb::CMs 1056655 Specdb::CMs 1056657 Specdb::CMs 1056659 Specdb::CMs 1056660 Specdb::CMs 1056662 Specdb::CMs 1056664 Specdb::CMs 1056666 Specdb::CMs 1056667 Specdb::CMs 1056669 Specdb::CMs 1056671 Specdb::CMs 1056673 Specdb::CMs 1056675 Specdb::CMs 1056677 Specdb::CMs 1056678 Specdb::CMs 1056680 Specdb::CMs 1056682 Specdb::CMs 1056684 Specdb::CMs 1056686 Specdb::CMs 1056688 Specdb::CMs 1056690 Specdb::NmrOneD 6402 Specdb::NmrOneD 6403 Specdb::NmrOneD 6404 Specdb::NmrOneD 6405 Specdb::NmrOneD 6406 Specdb::NmrOneD 6407 Specdb::NmrOneD 6408 Specdb::NmrOneD 6409 Specdb::NmrOneD 6410 Specdb::NmrOneD 6411 Specdb::NmrOneD 6412 Specdb::NmrOneD 6413 Specdb::NmrOneD 6414 Specdb::NmrOneD 6415 Specdb::NmrOneD 6416 Specdb::NmrOneD 6417 Specdb::NmrOneD 6418 Specdb::NmrOneD 6419 Specdb::NmrOneD 6420 Specdb::NmrOneD 6421 Specdb::MsMs 25517 Specdb::MsMs 25518 Specdb::MsMs 25519 Specdb::MsMs 32075 Specdb::MsMs 32076 Specdb::MsMs 32077 Specdb::MsMs 1471645 Specdb::MsMs 1471646 Specdb::MsMs 1471647 Specdb::MsMs 1471648 Specdb::MsMs 1471649 Specdb::MsMs 1471650 Specdb::MsMs 1471651 Specdb::MsMs 1471652 Specdb::MsMs 1471653 Specdb::MsMs 1471654 Specdb::MsMs 1471655 Specdb::MsMs 1471656 Specdb::MsMs 1471657 Specdb::MsMs 1471658 Specdb::MsMs 1471659 Specdb::MsMs 1471660 Specdb::MsMs 1473417 Specdb::MsMs 1473418 Specdb::MsMs 1475424 HMDB00280 7339 7062 C00119 17111 PRPP PRP Phosphoribosyl pyrophosphate Keseler, 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. 21097882 Kanehisa, 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. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). 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Epub 2001 Apr 4. 11290738 Blinov MN, Kamyshentsev MV, Luganova IS, Filanovskaia LI, Filippova VN: [Phosphoribosyl pyrophosphate and its metabolic enzymes in the erythrocytes in certain forms of anemia] Vopr Med Khim. 1976 Jul-Aug;22(4):456-62. 194412 Micheli V, Taddeo A: [Spectrophotometric assay of 5-phosphoribosyl-1-pyrophosphate synthetase (PRPP) in erythrocyte lysate (author's transl)] Quad Sclavo Diagn. 1981 Jun;17(2):209-15. 6267652 Sakuma R, Nishina T, Yamanaka H, Kamatani N, Nishioka K, Maeda M, Tsuji A: Phosphoribosylpyrophosphate synthetase in human erythrocytes: assay and kinetic studies using high-performance liquid chromatography. Clin Chim Acta. 1991 Dec 16;203(2-3):143-52. 1663846 Zoref-Shani E, Feinstein S, Frishberg Y, Bromberg Y, Sperling O: Kelley-Seegmiller syndrome due to a unique variant of hypoxanthine-guanine phosphoribosyltransferase: reduced affinity for 5-phosphoribosyl-1-pyrophosphate manifested only at low, physiological substrate concentrations. 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Clin Chim Acta. 1977 Jul 15;78(2):209-16. 195752 MacDermot KD, Allsop J, Watts RW: The rate of purine synthesis de nova in blood mononuclear cells in vitro from patients with familial hyperuricaemic nephropathy. Clin Sci (Lond). 1984 Aug;67(2):249-58. 6744792 Emmerson BT, Gordon RB, Thompson L: Adenine phosphoribosyltransferase deficiency: its inheritance and occurrence in a female with gout and renal disease. Aust N Z J Med. 1975 Oct;5(5):440-6. 1061547 Zerez CR, Lachant NA, Tanaka KR: Decreased erythrocyte phosphoribosylpyrophosphate synthetase activity and impaired formation in thalassemia minor: a mechanism for decreased adenine nucleotide content. J Lab Clin Med. 1989 Jul;114(1):43-50. 2544652 Rylance HJ, Wallace RC, Nuki G: A method for the determination of 5-phosphoribosyl 1-pyrophosphate concentrations in erythrocytes using high-performance liquid chromatography. Anal Biochem. 1987 Feb 1;160(2):337-41. 2437821 Kane MA, Roth E, Raptis G, Schreiber C, Waxman S: Effect of intracellular folate concentration on the modulation of 5-fluorouracil cytotoxicity by the elevation of phosphoribosylpyrophosphate in cultured human KB cells. Cancer Res. 1987 Dec 15;47(24 Pt 1):6444-50. 2445472 Lachant NA, Zerez CR, Tanaka KR: Pyrimidine nucleotides impair phosphoribosylpyrophosphate (PRPP) synthetase subunit aggregation by sequestering magnesium. A mechanism for the decreased PRPP synthetase activity in hereditary erythrocyte pyrimidine 5'-nucleotidase deficiency. Biochim Biophys Acta. 1989 Jan 19;994(1):81-8. 2535789 Gross, Akiva; Abril, Obsidiana; Lewis, Jerome M.; Geresh, Shimona; Whitesides, George M. Practical synthesis of 5-phospho-D-ribosyl a-1-pyrophosphate (PRPP): enzymatic routes from ribose 5-phosphate or ribose. Journal of the American Chemical Society ( Anthranilate synthase component II P00904 TRPG_ECOLI trpD http://ecmdb.ca/proteins/P00904.xml Ribose-phosphate pyrophosphokinase P0A717 KPRS_ECOLI prs http://ecmdb.ca/proteins/P0A717.xml Orotate phosphoribosyltransferase P0A7E3 PYRE_ECOLI pyrE http://ecmdb.ca/proteins/P0A7E3.xml Uracil phosphoribosyltransferase P0A8F0 UPP_ECOLI upp http://ecmdb.ca/proteins/P0A8F0.xml Hypoxanthine phosphoribosyltransferase P0A9M2 HPRT_ECOLI hpt http://ecmdb.ca/proteins/P0A9M2.xml Xanthine phosphoribosyltransferase P0A9M5 XGPT_ECOLI gpt http://ecmdb.ca/proteins/P0A9M5.xml Amidophosphoribosyltransferase P0AG16 PUR1_ECOLI purF http://ecmdb.ca/proteins/P0AG16.xml ATP-binding protein phnN P16690 PHNN_ECOLI phnN http://ecmdb.ca/proteins/P16690.xml Nicotinate phosphoribosyltransferase P18133 PNCB_ECOLI pncB http://ecmdb.ca/proteins/P18133.xml Nicotinate-nucleotide pyrophosphorylase [carboxylating] P30011 NADC_ECOLI nadC http://ecmdb.ca/proteins/P30011.xml ATP phosphoribosyltransferase P60757 HIS1_ECOLI hisG http://ecmdb.ca/proteins/P60757.xml Adenine phosphoribosyltransferase P69503 APT_ECOLI apt http://ecmdb.ca/proteins/P69503.xml Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate R01229 GUANPRIBOSYLTRAN-RXN Hypoxanthine + Phosphoribosyl pyrophosphate <> Inosinic acid + Pyrophosphate R01132 HYPOXANPRIBOSYLTRAN-RXN 2 Hydrogen ion + Phosphoribosyl pyrophosphate + Quinolinic acid <> Carbon dioxide + Nicotinamide ribotide + Pyrophosphate R03348 QUINOPRIBOTRANS-RXN Phosphoribosyl pyrophosphate + Xanthine <> Pyrophosphate + Xanthylic acid R02142 XANPRIBOSYLTRAN-RXN Adenine + Phosphoribosyl pyrophosphate <> Adenosine monophosphate + Pyrophosphate R00190 ADENPRIBOSYLTRAN-RXN Adenosine triphosphate + Water + Nicotinic acid + Phosphoribosyl pyrophosphate > ADP + Nicotinamide ribotide + Phosphate + Pyrophosphate Adenosine triphosphate + D-Ribose-5-phosphate <> Adenosine monophosphate + Hydrogen ion + Phosphoribosyl pyrophosphate R01049 PRPPSYN-RXN 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + N-(5-Phospho-D-ribosyl)anthranilate R01073 PRTRANS-RXN Adenosine triphosphate + Phosphoribosyl pyrophosphate <> Pyrophosphate + Phosphoribosyl-ATP R01071 ATPPHOSPHORIBOSYLTRANS-RXN L-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate + 5-Phosphoribosylamine R01072 PRPPAMIDOTRANS-RXN Phosphoribosyl pyrophosphate + Uracil <> Pyrophosphate + Uridine 5'-monophosphate R00966 URACIL-PRIBOSYLTRANS-RXN Orotidylic acid + Pyrophosphate <> Orotic acid + Phosphoribosyl pyrophosphate R01870 OROPRIBTRANS-RXN Adenosine triphosphate + Ribose 1,5-bisphosphate <> ADP + Phosphoribosyl pyrophosphate R06836 RXN0-1401 Adenosine monophosphate + Pyrophosphate <> Adenine + Phosphoribosyl pyrophosphate R00190 Uridine 5'-monophosphate + Pyrophosphate <> Uracil + Phosphoribosyl pyrophosphate R00966 Adenosine triphosphate + D-Ribose-5-phosphate <> Adenosine monophosphate + Phosphoribosyl pyrophosphate R01049 Phosphoribosyl-ATP + Pyrophosphate <> Adenosine triphosphate + Phosphoribosyl pyrophosphate R01071 5-Phosphoribosylamine + Pyrophosphate + L-Glutamate <> L-Glutamine + Phosphoribosyl pyrophosphate + Water R01072 N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate <> 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate R01073 Inosinic acid + Pyrophosphate <> Hypoxanthine + Phosphoribosyl pyrophosphate R01132 Guanosine monophosphate + Pyrophosphate <> Guanine + Phosphoribosyl pyrophosphate R01229 Nicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + Phosphate R01724 Xanthylic acid + Pyrophosphate <> Xanthine + Phosphoribosyl pyrophosphate R02142 Nicotinamide ribotide + Pyrophosphate + Carbon dioxide <> Quinolinic acid + Phosphoribosyl pyrophosphate R03348 AICAR + Pyrophosphate <> 5-Amino-4-imidazolecarboxyamide + Phosphoribosyl pyrophosphate R04378 6-Mercaptopurine + Phosphoribosyl pyrophosphate <> 6-Thioinosine-5'-monophosphate + Pyrophosphate R08237 6-Methylmercaptopurine + Phosphoribosyl pyrophosphate <> 6-Methylthiopurine 5'-monophosphate ribonucleotide + Pyrophosphate R08238 Thioguanine + Phosphoribosyl pyrophosphate <> 6-Thioguanosine monophosphate + Pyrophosphate R08245 Pyrophosphate + Adenosine monophosphate < Phosphoribosyl pyrophosphate + Adenine ADENPRIBOSYLTRAN-RXN Pyrophosphate + Inosinic acid < Phosphoribosyl pyrophosphate + Hypoxanthine HYPOXANPRIBOSYLTRAN-RXN Nicotinamide ribotide + Pyrophosphate < Hydrogen ion + Nicotinic acid + Phosphoribosyl pyrophosphate R01724 NICOTINATEPRIBOSYLTRANS-RXN 5-Phosphoribosylamine + Pyrophosphate + L-Glutamate < Phosphoribosyl pyrophosphate + L-Glutamine + Water R01072 PRPPAMIDOTRANS-RXN N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate < 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate PRTRANS-RXN Nicotinamide ribotide + Pyrophosphate + Carbon dioxide < Phosphoribosyl pyrophosphate + Quinolinic acid + Hydrogen ion QUINOPRIBOTRANS-RXN Ribose 1,5-bisphosphate + Adenosine triphosphate > Phosphoribosyl pyrophosphate + ADP R06836 RXN0-1401 Pyrophosphate + Uridine 5'-monophosphate < Phosphoribosyl pyrophosphate + Uracil URACIL-PRIBOSYLTRANS-RXN Xanthylic acid + Pyrophosphate < Xanthine + Phosphoribosyl pyrophosphate R02142 XANPRIBOSYLTRAN-RXN Adenosine monophosphate + Pyrophosphate > Adenine + Phosphoribosyl pyrophosphate Phosphoribosyl-ATP + Pyrophosphate > Adenosine triphosphate + Phosphoribosyl pyrophosphate Inosinic acid + Pyrophosphate > Hypoxanthine + Phosphoribosyl pyrophosphate Adenosine triphosphate + D-Ribose-5-phosphate > Adenosine monophosphate + Phosphoribosyl pyrophosphate Nicotinamide ribotide + Pyrophosphate + Carbon dioxide > Quinolinic acid + Phosphoribosyl pyrophosphate Nicotinamide ribotide + Pyrophosphate > Nicotinic acid + Phosphoribosyl pyrophosphate R01724 NICOTINATEPRIBOSYLTRANS-RXN 5-Phosphoribosylamine + Pyrophosphate + L-Glutamate > L-Glutamine + Phosphoribosyl pyrophosphate + Water Orotidylic acid + Pyrophosphate > Orotic acid + Phosphoribosyl pyrophosphate N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate > 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate Uridine 5'-monophosphate + Pyrophosphate > Uracil + Phosphoribosyl pyrophosphate Xanthylic acid + Pyrophosphate > Phosphoribosyl pyrophosphate + Xanthine Phosphoribosyl pyrophosphate + Hydrogen ion > Pyrophosphate + Phosphoribosyl-ATP + Phosphoribosyl-ATP PW_R002865 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate PW_R002895 Quinolinic acid + Hydrogen ion + Phosphoribosyl pyrophosphate > Carbon dioxide + Pyrophosphate + nicotinate beta-D-ribonucleotide + Nicotinamide ribotide PW_R003009 Nicotinic acid + Water + Adenosine triphosphate + Phosphoribosyl pyrophosphate > Phosphate + Adenosine diphosphate + Pyrophosphate + nicotinate beta-D-ribonucleotide + ADP + Nicotinamide ribotide PW_R003016 D-Ribose-5-phosphate + Adenosine triphosphate > Hydrogen ion + Adenosine monophosphate + Phosphoribosyl pyrophosphate PW_R003406 Ribose 1,5-bisphosphate + Adenosine triphosphate + Ribose 1,5-bisphosphate > Adenosine diphosphate + Phosphoribosyl pyrophosphate + ADP PW_R003409 Phosphoribosyl pyrophosphate + Water + L-Glutamine > 5-Phosphoribosylamine + L-Glutamic acid + Pyrophosphate + 5-Phosphoribosylamine + L-Glutamate PW_R003410 Orotic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + Orotidylic acid PW_R003529 Hypoxanthine + Phosphoribosyl pyrophosphate > Inosinic acid + Pyrophosphate PW_R006052 Guanine + Phosphoribosyl pyrophosphate > Pyrophosphate + Guanosine monophosphate PW_R006059 Adenine + Phosphoribosyl pyrophosphate > Pyrophosphate + Adenosine monophosphate PW_R006055 Xanthine + Phosphoribosyl pyrophosphate > Xanthylic acid + Pyrophosphate PW_R006088 Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate L-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate +5 5-Phosphoribosylamine 5 5-Phosphoribosylamine + Pyrophosphate + L-Glutamate <> L-Glutamine + Phosphoribosyl pyrophosphate + Water Adenosine triphosphate + Phosphoribosyl pyrophosphate <> Pyrophosphate + Phosphoribosyl-ATP Phosphoribosyl-ATP + Pyrophosphate <> Adenosine triphosphate + Phosphoribosyl pyrophosphate 2 Hydrogen ion + Phosphoribosyl pyrophosphate + Quinolinic acid <> Carbon dioxide + Nicotinamide ribotide + Pyrophosphate Phosphoribosyl pyrophosphate + Uracil <> Pyrophosphate + Uridine 5'-monophosphate Adenosine triphosphate + D-Ribose-5-phosphate <> Adenosine monophosphate + Hydrogen ion + Phosphoribosyl pyrophosphate Nicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + Phosphate Orotidylic acid + Pyrophosphate <> Orotic acid + Phosphoribosyl pyrophosphate Guanine + Phosphoribosyl pyrophosphate > Guanosine monophosphate + Pyrophosphate L-Glutamine + Water + Phosphoribosyl pyrophosphate <> L-Glutamate + Pyrophosphate +5 5-Phosphoribosylamine Adenosine triphosphate + Phosphoribosyl pyrophosphate <> Pyrophosphate + Phosphoribosyl-ATP 2 Hydrogen ion + Phosphoribosyl pyrophosphate + Quinolinic acid <> Carbon dioxide + Nicotinamide ribotide + Pyrophosphate Phosphoribosyl pyrophosphate + Uracil <> Pyrophosphate + Uridine 5'-monophosphate Nicotinamide ribotide + Pyrophosphate + Adenosine triphosphate + Water <> Nicotinic acid + Phosphoribosyl pyrophosphate + ADP + Phosphate Orotidylic acid + Pyrophosphate <> Orotic acid + Phosphoribosyl pyrophosphate Gutnick 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 glucose Shake flask and filter culture 258.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 1032000 0 Bennett, 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. 19561621 Gutnick 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 glycerol Shake flask and filter culture 153.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 612000 0 Bennett, 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. 19561621 Gutnick 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 acetate Shake flask and filter culture 94.4 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 377600 0 Bennett, 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. 19561621