2.0 2012-05-31 13:54:45 -0600 2015-09-17 15:41:12 -0600 ECMDB01846 M2MDB000424 Tetrahydrofolic acid Tetrahydrofolate is a soluble coenzyme (vitamin B9) that is synthesized de novo by plants and microorganisms, and absorbed from the diet by animals. It is composed of three distinct parts: a pterin ring, a p-ABA (p-aminobenzoic acid) and a polyglutamate chain with a number of residues varying between 1 and 8. Only the tetra-reduced form of the molecule serves as a coenzyme for C1 transfer reactions. In biological systems, the C1-units exist under various oxidation states and the different tetrahydrofolate derivatives constitute a family of related molecules named indistinctly under the generic term folate. (PMID 16042593) (6S)-Tetrahydrofolate (6S)-Tetrahydrofolic acid 5,6,7,8-Tetrahydrofolate 5,6,7,8-Tetrahydrofolic acid FH4 Folate-H4 Folic acid-H4 H4F H4PteGlu H4PteGlu1 H₄PteGlu₁ Tetra-H-folate Tetra-H-folic acid Tetrahydrafolate Tetrahydrafolic acid Tetrahydrofolate Tetrahydrofolic acid Tetrahydropteroyl mono-L-glutamate Tetrahydropteroyl mono-L-glutamic acid Tetrahydropteroylglutamate Tetrahydropteroylglutamic acid Th-folate Th-folic acid THF Vitamin B9 C19H23N7O6 445.4292 445.170981503 (2S)-2-{[4-({[(6S)-4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid (2S)-2-{[4-({[(6S)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid 135-16-0 NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)N2)N1 InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12?/m0/s1 MSTNYGQPCMXVAQ-PXYINDEMSA-N Solid Cytosol logp -1.43 ALOGPS logs -3.32 ALOGPS solubility 2.15e-01 g/l ALOGPS melting_point 250 oC (523 K), decomp. logp -5.3 ChemAxon pka_strongest_acidic -13 ChemAxon pka_strongest_basic 15 ChemAxon iupac (2S)-2-{[4-({[(6S)-4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid ChemAxon average_mass 445.4292 ChemAxon mono_mass 445.170981503 ChemAxon smiles NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)N2)N1 ChemAxon formula C19H23N7O6 ChemAxon inchi InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12?/m0/s1 ChemAxon inchikey MSTNYGQPCMXVAQ-PXYINDEMSA-N ChemAxon polar_surface_area 208.26 ChemAxon refractivity 132.4 ChemAxon polarizability 44.33 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 12 ChemAxon donor_count 9 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Nitrogen metabolism The biological process of the nitrogen cycle is a complex interplay among many microorganisms catalyzing different reactions, where nitrogen is found in various oxidation states ranging from +5 in nitrate to -3 in ammonia. The ability of fixing atmospheric nitrogen by the nitrogenase enzyme complex is present in restricted prokaryotes (diazotrophs). The other reduction pathways are assimilatory nitrate reduction and dissimilatory nitrate reduction both for conversion to ammonia, and denitrification. Denitrification is a respiration in which nitrate or nitrite is reduced as a terminal electron acceptor under low oxygen or anoxic conditions, producing gaseous nitrogen compounds (N2, NO and N2O) to the atmosphere. Nitrate can be introduced into the cytoplasm through a nitrate:nitrite antiporter NarK or a nitrate / nitrite transporter NarU. Nitrate is then reduced by a Nitrate Reductase resulting in the release of water, an acceptor and a Nitrite. Nitrite can also be introduced into the cytoplasm through a nitrate:nitrite antiporter NarK Nitrite can be reduced a NADPH dependent nitrite reductase resulting in water and NAD and Ammonia. Nitrite can interact with hydrogen ion, ferrocytochrome c through a cytochrome c-552 ferricytochrome resulting in the release of ferricytochrome c, water and ammonia Another process by which ammonia is produced is by a reversible reaction of hydroxylamine with a reduced acceptor through a hydroxylamine reductase resulting in an acceptor, water and ammonia. Water and carbon dioxide react through a carbonate dehydratase resulting in carbamic acid. This compound reacts spontaneously with hydrogen ion resulting in the release of carbon dioxide and ammonia. Carbon dioxide can interact with water through a carbonic anhydrase resulting in hydrogen carbonate. This compound interacts with cyanate and hydrogen ion through a cyanate hydratase resulting in a carbamic acid. Ammonia can be metabolized by reacting with L-glutamine and ATP driven glutamine synthetase resulting in ADP, phosphate and L-glutamine. The latter compound reacts with oxoglutaric acid and hydrogen ion through a NADPH dependent glutamate synthase resulting in the release of NADP and L-glutamic acid. L-glutamic acid reacts with water through a NADP-specific glutamate dehydrogenase resulting in the release of oxoglutaric acid, NADPH, hydrogen ion and ammonia. PW000755 ec00910 Metabolic Purine metabolism ec00230 Cysteine and methionine metabolism ec00270 Glycine, serine and threonine metabolism ec00260 Amino sugar and nucleotide sugar metabolism ec00520 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 Cyanoamino acid metabolism ec00460 Methane metabolism ec00680 Pantothenate and CoA biosynthesis The CoA biosynthesis requires compounds from two other pathways: aspartate metabolism and valine biosynthesis. It requires a Beta-Alanine and R-pantoate. The compound (R)-pantoate is generated in two reactions, as shown by the interaction of alpha-ketoisovaleric acid, 5,10 methylene-THF and water through a 3-methyl-2-oxobutanoate hydroxymethyltransferase resulting in a tetrahydrofolic acid and a 2-dehydropantoate. This compound interacts with hydrogen through a NADPH driven acetohydroxy acid isomeroreductase resulting in the release of NADP and R-pantoate. On the other hand L-aspartic acid interacts with a hydrogen ion and gets decarboxylated through an Aspartate 1- decarboxylase resulting in a carbon dioxide and a Beta-alanine. Beta-alanine and R-pantoate interact with an ATP driven pantothenate synthetase resulting in pyrophosphate, AMP, hydrogen ion and pantothenic acid. Pantothenic acid is phosphorylated through a ATP-driven pantothenate kinase resulting in a ADP, a hydrogen ion and D-4'-Phosphopantothenate. This compound interacts with a CTP and a L-cysteine resulting in a fused 4'-phosphopantothenoylcysteine decarboxylase and phosphopantothenoylcysteine synthetase resulting in a hydrogen ion, a pyrophosphate, a CMP and 4-phosphopantothenoylcysteine. The latter compound interacts with a hydrogen ion through a fused 4'-phosphopantothenoylcysteine decarboxylase and phosphopantothenoylcysteine synthetase resulting in a carbon dioxide release and a 4-phosphopantetheine. This compound interacts with an ATP, hydrogen ion and an phosphopantetheine adenylyltransferase resulting in a release of pyrophosphate, and dephospho-CoA. Dephospho-CoA reacts with an ATP driven dephospho-CoA kinase resulting in a ADP , a hydrogen ion and a Coenzyme A. . The latter is converted into (R)-4'-phosphopantothenate is two steps, involving a β-alanine ligase and a kinase. In most organsims the ligase acts before the kinase (EC 6.3.2.1, pantoate—β-alanine ligase (AMP-forming) followed by EC 2.7.1.33, pantothenate kinase, as described in phosphopantothenate biosynthesis I and phosphopantothenate biosynthesis II. However, in archaea the order is reversed, and EC 2.7.1.169, pantoate kinase acts before EC 6.3.2.36, 4-phosphopantoate—β-alanine ligase, as described in phosphopantothenate biosynthesis III. The kinases are feedback inhibited by CoA itself, accounting for the primary regulatory mechanism of CoA biosynthesis. The addition of L-cysteine to (R)-4'-phosphopantothenate, resulting in the formation of R-4'-phosphopantothenoyl-L-cysteine (PPC), is followed by decarboxylation of PPC to 4'-phosphopantetheine. The ultimate reaction is catalyzed by EC 2.7.1.24, dephospho-CoA kinase, which converts 4'-phosphopantetheine to CoA. All enzymes of this pathway are essential for growth. The reactions in the biosynthetic route towards CoA are identical in most organisms, although there are differences in the functionality of the involved enzymes. In plants every step is catalyzed by single monofunctional enzymes, whereas in bacteria and mammals bifunctional enzymes are often employed [Rubio06]. PW000828 ec00770 Metabolic Selenoamino acid metabolism ec00450 Aminoacyl-tRNA biosynthesis ec00970 Glyoxylate and dicarboxylate metabolism ec00630 One carbon pool by folate Dihydrofolic 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. PW000773 ec00670 Metabolic Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 GLYCINE BIOSYNTHESIS One step pathway for glycine biosynthesis dependent on L-serine, is a major source of one-carbon units in the form of 5,10-methylene tetrahydrofolate. L-serine is enters cell through transporters (serine / threonine:H+ symporter TdcC, serine/threonine: Na symporter , serine:H+ symporter SdaC ) and then proceeds through reversible reaction with a tetrahydrofolic acid through a serine hydroxymethyltransferase enzyme in order to produce glycine, 5,10-methylene tetrahydrofolate and water PW000808 Metabolic One Carbon Pool by Folate I Dihydrofolic 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. PW001735 Metabolic polymyxin resistance UDP-glucuronic acid compound undergoes a NAD dependent reaction through a bifunctional polymyxin resistance protein to produce UDP-Beta-L-threo-pentapyranos-4-ulose. This compound then reacts with L-glutamic acid through a UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase to produce an oxoglutaric acid and UDP-4-amino-4-deoxy-beta-L-arabinopyranose The latter compound interacts with a N10-formyl-tetrahydrofolate through a bifunctional polymyxin resistance protein ArnA, resulting in a tetrahydrofolate, a hydrogen ion and a UDP-4-deoxy-4-formamido-beta-L-arabinopyranose, which in turn reacts with a product of the methylerythritol phosphate and polysoprenoid biosynthesis pathway, di-trans,octa-cis-undecaprenyl phosphate to produce a 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate. The compound 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate hypothetically reacts with water and results in the release of a formic acid and 4-amino-4-deoxy-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate which in turn reacts with a KDO2-lipid A through a 4-amino-4-deoxy-L-arabinose transferase resulting in the release of a di-trans,octa-cis-undecaprenyl phosphate and a L-Ara4N-modified KDO2-Lipid A PW002052 Metabolic S-adenosyl-L-methionine cycle The S-adenosyl-L-methionine cycle starts with S-adenosyl-L-methionine reacting with (a demethylated methyl donor ) dimethylglycine resulting in the release of a hydrogen ion, a betain (a methylated methyl donor) and a S-adenosyl-L-homocysteine. The s-adenosyl-L-homocysteine reacts with a water molecule through a S-adenosylhomocysteine nucleosidase resulting in the release of a adenine and a ribosyl-L-homocysteine. This compound in turn reacts with a s-ribosylhomocysteine lyase resulting in the release of a l-homocysteine and a autoinducer 2. The L-homocysteine reacts with a N5-methyl-tetrahydropteroyl tri-L-glutamate through a methionine synthase resulting in the release of a tetrahydropteroyl tri-L-glutamate and a methione. The methionine in turn reacts with a water molecule and ATP molecule through a methionine adenosyltransferase resulting in the release of a diphosphate, a phosphate and a s-adenosyl-L-methionine. PW002080 Metabolic phosphopantothenate biosynthesis I PANTO-PWY formylTHF biosynthesis I 1CMET2-PWY glycine cleavage complex GLYCLEAV-PWY methionine biosynthesis I HOMOSER-METSYN-PWY superpathway of serine and glycine biosynthesis I GLYSYN-PWY folate polyglutamylation PWY-2161 5-aminoimidazole ribonucleotide biosynthesis I PWY-6121 polymyxin resistance PWY0-1338 tetrahydrofolate biosynthesis PWY-6614 inosine-5'-phosphate biosynthesis I PWY-6123 tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate PWY-6613 Specdb::CMs 1083818 Specdb::EiMs 5072 Specdb::MsMs 27965 Specdb::MsMs 27966 Specdb::MsMs 27967 Specdb::MsMs 34523 Specdb::MsMs 34524 Specdb::MsMs 34525 HMDB01846 1129 1097 C00101 15635 THF THL Tetrahydrofolic acid 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 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 Sahr, T., Ravanel, S., Rebeille, F. (2005). "Tetrahydrofolate biosynthesis and distribution in higher plants." Biochem Soc Trans 33:758-762. 16042593 http://hmdb.ca/system/metabolites/msds/000/001/437/original/Tetrahydrofolic_acid_MSDS.pdf?1368653263 Phosphoribosylglycinamide formyltransferase P08179 PUR3_ECOLI purN http://ecmdb.ca/proteins/P08179.xml Bifunctional protein folC P08192 FOLC_ECOLI folC http://ecmdb.ca/proteins/P08192.xml Serine hydroxymethyltransferase P0A825 GLYA_ECOLI glyA http://ecmdb.ca/proteins/P0A825.xml Dihydrolipoyl dehydrogenase P0A9P0 DLDH_ECOLI lpdA http://ecmdb.ca/proteins/P0A9P0.xml Dihydrofolate reductase P0ABQ4 DYR_ECOLI folA http://ecmdb.ca/proteins/P0ABQ4.xml Dihydrofolate reductase folM P0AFS3 FOLM_ECOLI folM http://ecmdb.ca/proteins/P0AFS3.xml Methionine synthase P13009 METH_ECOLI metH http://ecmdb.ca/proteins/P13009.xml Bifunctional purine biosynthesis protein purH P15639 PUR9_ECOLI purH http://ecmdb.ca/proteins/P15639.xml Methionyl-tRNA formyltransferase P23882 FMT_ECOLI fmt http://ecmdb.ca/proteins/P23882.xml 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase P25665 METE_ECOLI metE http://ecmdb.ca/proteins/P25665.xml Aminomethyltransferase P27248 GCST_ECOLI gcvT http://ecmdb.ca/proteins/P27248.xml 3-methyl-2-oxobutanoate hydroxymethyltransferase P31057 PANB_ECOLI panB http://ecmdb.ca/proteins/P31057.xml Glycine dehydrogenase [decarboxylating] P33195 GCSP_ECOLI gcvP http://ecmdb.ca/proteins/P33195.xml Phosphoribosylglycinamide formyltransferase 2 P33221 PURT_ECOLI purT http://ecmdb.ca/proteins/P33221.xml Formyltetrahydrofolate deformylase P37051 PURU_ECOLI purU http://ecmdb.ca/proteins/P37051.xml Bifunctional polymyxin resistance protein ArnA P77398 ARNA_ECOLI arnA http://ecmdb.ca/proteins/P77398.xml Glycine cleavage system H protein P0A6T9 GCSH_ECOLI gcvH http://ecmdb.ca/proteins/P0A6T9.xml Dihydrofolic acid + Hydrogen ion + NADPH <> NADP + Tetrahydrofolic acid R00939 DIHYDROFOLATEREDUCT-RXN Glycine + NAD + Tetrahydrofolic acid > Carbon dioxide + 5,10-Methylene-THF + NADH + Ammonium 5-Methyltetrahydrofolic acid + L-Homocysteine <> Hydrogen ion + L-Methionine + Tetrahydrofolic acid R00946 HOMOCYSMETB12-RXN alpha-Ketoisovaleric acid + Water + 5,10-Methylene-THF + a-Ketoisovaleric acid <> 2-Dehydropantoate + Tetrahydrofolic acid R01226 3-CH3-2-OXOBUTANOATE-OH-CH3-XFER-RXN N10-Formyl-THF + Water <> Formic acid + Hydrogen ion + Tetrahydrofolic acid R00944 FORMYLTHFDEFORMYL-RXN N10-Formyl-THF + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose <> Hydrogen ion + Tetrahydrofolic acid + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose R07660 RXN0-1862 N10-Formyl-THF + Glycineamideribotide <> 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid R04325 GART-RXN L-Serine + Tetrahydrofolic acid <> Glycine + Water + 5,10-Methylene-THF R00945 GLYOHMETRANS-RXN N10-Formyl-THF + L-Methionyl-tRNA (Met) > N-Formylmethionyl-tRNA + Hydrogen ion + Tetrahydrofolic acid N10-Formyl-THF + Phosphoribosyl formamidocarboxamide <> Phosphoribosyl formamidocarboxamide + Tetrahydrofolic acid Tetrahydrofolic acid + NAD <> Dihydrofolic acid + NADH + Hydrogen ion R00936 Tetrahydrofolic acid + 2 NAD <> Folic acid +2 NADH +2 Hydrogen ion R00937 Tetrahydrofolic acid + NADP <> Dihydrofolic acid + NADPH + Hydrogen ion R00939 Tetrahydrofolic acid + 2 NADP <> Folic acid +2 NADPH +2 Hydrogen ion R00940 Adenosine triphosphate + Tetrahydrofolic acid + L-Glutamate <> ADP + Phosphate + Tetrahydrofolyl-[Glu](2) R00942 N10-Formyl-THF + Water <> Formic acid + Tetrahydrofolic acid R00944 5,10-Methylene-THF + Glycine + Water <> Tetrahydrofolic acid + L-Serine R00945 GLYOHMETRANS-RXN 5-Methyltetrahydrofolic acid + L-Homocysteine <> Tetrahydrofolic acid + L-Methionine R00946 Glycine + Tetrahydrofolic acid + NAD <> 5,10-Methylene-THF + Ammonia + Carbon dioxide + NADH + Hydrogen ion R01221 5,10-Methylene-THF + alpha-Ketoisovaleric acid + Water <> Tetrahydrofolic acid + 2-Dehydropantoate R01226 L-Methionyl-tRNA + N10-Formyl-THF <> Tetrahydrofolic acid + N-Formylmethionyl-tRNA R03940 S-Aminomethyldihydrolipoylprotein + Tetrahydrofolic acid + S-Aminomethyldihydrolipoylprotein <> Dihydrolipoylprotein + 5,10-Methylene-THF + Ammonia R04125 N10-Formyl-THF + Glycineamideribotide <> Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide R04325 Glycineamideribotide + 5,10-Methenyltetrahydrofolate + Water <> 5'-Phosphoribosyl-N-formylglycineamide + Tetrahydrofolic acid R04326 N10-Formyl-THF + AICAR <> Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide R04560 N10-Formyl-THF + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose <> Tetrahydrofolic acid + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose R07660 NAD + Glycine + Tetrahydrofolic acid > Hydrogen ion + 5,10-Methylene-THF + Ammonia + Carbon dioxide + NADH R01221 GCVMULTI-RXN Formaldehyde + Tetrahydrofolic acid > 5,10-Methylene-THF + Water RXN-2881 NADP + Tetrahydrofolic acid < Hydrogen ion + NADPH + Dihydrofolic acid DIHYDROFOLATEREDUCT-RXN Adenosine triphosphate + Formic acid + Tetrahydrofolic acid > ADP + Phosphate + N10-Formyl-THF FORMATETHFLIG-RXN Water + N10-Formyl-THF > Hydrogen ion + Tetrahydrofolic acid + Formic acid FORMYLTHFDEFORMYL-RXN L-Homocysteine + 5-Methyltetrahydrofolic acid L-Methionine + Tetrahydrofolic acid HOMOCYSMETB12-RXN Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + N10-Formyl-THF > Hydrogen ion + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose + Tetrahydrofolic acid RXN0-1862 N10-Formyl-THF + 4-Amino-4-deoxy-L-arabinose > Tetrahydrofolic acid + UDP-4-Deoxy-4-formamido-beta-L-arabinose Tetrahydrofolic acid + NADP > Dihydrofolic acid + NADPH N10-Formyl-THF + L-methionyl-tRNA(fMet) > Tetrahydrofolic acid + N-formylmethionyl-tRNA(fMet) [Protein]-S(8)-aminomethyldihydrolipoyllysine + Tetrahydrofolic acid > [protein]-dihydrolipoyllysine + 5,10-Methylene-THF + Ammonia 5,10-Methylene-THF + Glycine + Water > Tetrahydrofolic acid + L-Serine 5-Methyltetrahydrofolic acid + L-Homocysteine > Tetrahydrofolic acid + L-Methionine 5,10-Methylene-THF + a-Ketoisovaleric acid + Water > Tetrahydrofolic acid + 2-Dehydropantoate N10-Formyl-THF + 5'-Phospho-ribosylglycinamide > Tetrahydrofolic acid + 5'-phosphoribosyl-N-formylglycinamide N10-Formyl-THF + AICAR > Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide R04560 AICARTRANSFORM-RXN N10-Formyl-THF + Water > Formic acid + Tetrahydrofolic acid Dihydrofolic acid + NADPH + Hydrogen ion + Dihydrofolic acid + NADPH > Tetrahydrofolic acid + NADP + Tetrahydrofolic acid PW_R002538 7,8-dihydrofolate monoglutamate + Hydrogen ion + NADPH + Dihydrofolic acid + NADPH > NADP + Tetrahydrofolic acid + Tetrahydrofolic acid PW_R003405 Folic acid + 2 NADPH + 2 Hydrogen ion + 2 NADPH > Tetrahydrofolic acid +2 NADP + Tetrahydrofolic acid PW_R004674 5-Methyltetrahydrofolic acid + Homocysteine + 5-Methyltetrahydrofolic acid + Homocysteine > Tetrahydrofolic acid + L-Methionine + Tetrahydrofolic acid PW_R002542 S-Aminomethyldihydrolipoylprotein; + Tetrahydrofolic acid + Tetrahydrofolic acid <> 5,10-Methylene-THF + Ammonia + dihydrolipoylprotein + 5,10-Methylene-THF PW_R002543 Tetrahydrofolic acid + L-Serine + Tetrahydrofolic acid + L-Serine <> 5,10-Methylene-THF + Glycine + Water + 5,10-Methylene-THF PW_R002544 Tetrahydrofolic acid + FAICAR + Tetrahydrofolic acid > 10-Formyltetrahydrofolate + AICAR + N10-Formyl-THF PW_R002545 Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide > Water + 5,10-Methenyltetrahydrofolic acid + Glycineamideribotide + Glycineamideribotide PW_R002546 Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide > 10-Formyltetrahydrofolate + Glycineamideribotide + N10-Formyl-THF + Glycineamideribotide PW_R002547 5'-phosphoribosyl-a-N-formylglycineamidine + Tetrahydrofolic acid + Tetrahydrofolic acid > Water + Glycineamideribotide + 5,10-Methenyltetrahydrofolic acid + Glycineamideribotide PW_R002550 Formic acid + Tetrahydrofolic acid + Tetrahydrofolic acid > Water + 10-Formyltetrahydrofolate + N10-Formyl-THF PW_R002548 Tetrahydrofolic acid + N-formylmethionyl-tRNA(fMet) + Tetrahydrofolic acid L-methionyl-tRNA(Met) + 10-Formyltetrahydrofolate + N10-Formyl-THF PW_R002549 a-Ketoisovaleric acid + 5,10-Methylene-THF + Water + 5,10-Methylene-THF > Tetrahydrofolic acid + 2-dehydropantoate + Tetrahydrofolic acid + 2-Dehydropantoate PW_R002999 Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + an N10-formyl-tetrahydrofolate + N10-Formyl-THF > UDP-4-Deoxy-4-formamido-beta-L-arabinose + Hydrogen ion + a tetrahydrofolate + Tetrahydrofolic acid PW_R003358 L-Methionyl-tRNA + N10-Formyl-THF <> Tetrahydrofolic acid + N-Formylmethionyl-tRNA Dihydrofolic acid + Hydrogen ion + NADPH <> NADP + Tetrahydrofolic acid N10-Formyl-THF + Glycineamideribotide <>5 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid 5 5-Methyltetrahydrofolic acid + L-Homocysteine <> Hydrogen ion + L-Methionine + Tetrahydrofolic acid alpha-Ketoisovaleric acid + Water + 5 5,10-Methylene-THF + a-Ketoisovaleric acid <>2 2-Dehydropantoate + Tetrahydrofolic acid N10-Formyl-THF + AICAR <> Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide Glycine + Tetrahydrofolic acid + NAD <>5 5,10-Methylene-THF + Ammonia + Carbon dioxide + NADH + Hydrogen ion Dihydrofolic acid + Hydrogen ion + NADPH <> NADP + Tetrahydrofolic acid N10-Formyl-THF + Glycineamideribotide <>5 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid 5 5-Methyltetrahydrofolic acid + L-Homocysteine <> Hydrogen ion + L-Methionine + Tetrahydrofolic acid Dihydrofolic acid + Hydrogen ion + NADPH <> NADP + Tetrahydrofolic acid Glycine + Tetrahydrofolic acid + NAD <>5 5,10-Methylene-THF + Ammonia + Carbon dioxide + NADH + Hydrogen ion