2.0 2012-05-31 13:50:44 -0600 2015-09-17 15:41:12 -0600 ECMDB01354 M2MDB000353 5,10-Methylene-THF 5,10-Methylene-THF is an intermediate in the metabolism of methane and the metabolism of nitrogen. 5,10-Methylenetetrahydrofolate (5,10-CH2-THF) is the substrate used by the enzyme methylenetetrahydrofolate reductase (MTHFR) to generate 5-methyltetrahydrofolate (5-MTHF, or levomefolic acid). 5,10-CH2-THF can also be used as a coenzyme in the biosynthesis of thymidine. More specifically it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). It also acts as a coenzyme in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase. Methylenetetrahydrofolate reductase catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a cosubstrate for homocysteine remethylation to methionine. (6R)-5,10-methylenetetrahydrofolate (6R)-5,10-methylenetetrahydrofolic acid 5,10-Methenyltetrahydropteroylglutamate 5,10-Methenyltetrahydropteroylglutamic acid 5,10-Methylene-6-Hydrofolate 5,10-Methylene-6-Hydrofolic acid 5,10-Methylene-THF 5,10-Methylenetetrahydrofolate 5,10-Methylenetetrahydrofolic acid 5,10-Methylenetetrahydropteroyl mono-L-glutamate 5,10-Methylenetetrahydropteroyl mono-L-glutamic acid 5,10MeL-THF N5,N10-methylenetetrahydrofolate N5,N10-methylenetetrahydrofolic acid N5>,N10-methylenetetrahydrofolate N5>,N10-methylenetetrahydrofolic acid N<SUP>5</SUP>,N<SUP>10</SUP>-methylenetetrahydrofolate C20H23N7O6 457.4399 457.170981503 (2S)-2-({4-[(6aR)-3-amino-1-oxo-1H,2H,5H,6H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid 5,10-Methylene-THF 31690-11-6 [H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)NC(CCC(O)=O)C(O)=O InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13?/m1/s1 QYNUQALWYRSVHF-PZORYLMUSA-N Solid Cytosol logp -0.94 ALOGPS logs -2.75 ALOGPS solubility 8.23e-01 g/l ALOGPS logp -2 ChemAxon pka_strongest_acidic 2.93 ChemAxon pka_strongest_basic 4.6 ChemAxon iupac (2S)-2-({4-[(6aR)-3-amino-1-oxo-1H,2H,5H,6H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid ChemAxon average_mass 457.4399 ChemAxon mono_mass 457.170981503 ChemAxon smiles [H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)NC(CCC(O)=O)C(O)=O ChemAxon formula C20H23N7O6 ChemAxon inchi InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13?/m1/s1 ChemAxon inchikey QYNUQALWYRSVHF-PZORYLMUSA-N ChemAxon polar_surface_area 189.69 ChemAxon refractivity 123.96 ChemAxon polarizability 45.76 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 11 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Reductive carboxylate cycle (CO2 fixation) ec00720 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 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 Glycine, serine and threonine metabolism ec00260 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 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 phosphopantothenate biosynthesis I PANTO-PWY formylTHF biosynthesis I 1CMET2-PWY glycine cleavage complex GLYCLEAV-PWY pyrimidine deoxyribonucleotides <i>de novo</i> biosynthesis I PWY0-166 superpathway of serine and glycine biosynthesis I GLYSYN-PWY folate polyglutamylation PWY-2161 Specdb::CMs 1084393 Specdb::EiMs 5032 Specdb::NmrOneD 295815 Specdb::NmrOneD 295816 Specdb::NmrOneD 295817 Specdb::NmrOneD 295818 Specdb::NmrOneD 295819 Specdb::NmrOneD 295820 Specdb::NmrOneD 295821 Specdb::NmrOneD 295822 Specdb::NmrOneD 295823 Specdb::NmrOneD 295824 Specdb::NmrOneD 295825 Specdb::NmrOneD 295826 Specdb::NmrOneD 295827 Specdb::NmrOneD 295828 Specdb::NmrOneD 295829 Specdb::NmrOneD 295830 Specdb::NmrOneD 295831 Specdb::NmrOneD 295832 Specdb::NmrOneD 295833 Specdb::NmrOneD 295834 Specdb::MsMs 23048 Specdb::MsMs 23049 Specdb::MsMs 23050 Specdb::MsMs 29846 Specdb::MsMs 29847 Specdb::MsMs 29848 HMDB01533 388320 C00143 15636 METHYLENE-THF MHF 5,10-methylenetetrahydrofolate Keseler, I. 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Serine hydroxymethyltransferase P0A825 GLYA_ECOLI glyA http://ecmdb.ca/proteins/P0A825.xml Thymidylate synthase P0A884 TYSY_ECOLI thyA http://ecmdb.ca/proteins/P0A884.xml Dihydrolipoyl dehydrogenase P0A9P0 DLDH_ECOLI lpdA http://ecmdb.ca/proteins/P0A9P0.xml 5,10-methylenetetrahydrofolate reductase P0AEZ1 METF_ECOLI metF http://ecmdb.ca/proteins/P0AEZ1.xml Bifunctional protein folD P24186 FOLD_ECOLI folD http://ecmdb.ca/proteins/P24186.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 Glycine cleavage system H protein P0A6T9 GCSH_ECOLI gcvH http://ecmdb.ca/proteins/P0A6T9.xml Glycine + NAD + Tetrahydrofolic acid > Carbon dioxide + 5,10-Methylene-THF + NADH + Ammonium alpha-Ketoisovaleric acid + Water + 5,10-Methylene-THF + a-Ketoisovaleric acid <> 2-Dehydropantoate + Tetrahydrofolic acid R01226 3-CH3-2-OXOBUTANOATE-OH-CH3-XFER-RXN 5,10-Methylene-THF + NADP <> 5,10-Methenyltetrahydrofolate + NADPH + Hydrogen ion R01220 METHYLENETHFDEHYDROG-NADP-RXN L-Serine + Tetrahydrofolic acid <> Glycine + Water + 5,10-Methylene-THF R00945 GLYOHMETRANS-RXN dUMP + 5,10-Methylene-THF <> Dihydrofolic acid + 5-Thymidylic acid R02101 THYMIDYLATESYN-RXN 2 Hydrogen ion + 5,10-Methylene-THF + NADH > 5-Methyltetrahydrofolic acid + NAD R07168 1.5.1.20-RXN 5,10-Methylene-THF + Glycine + Water <> Tetrahydrofolic acid + L-Serine R00945 GLYOHMETRANS-RXN 5,10-Methylene-THF + NADP <> 5,10-Methenyltetrahydrofolate + NADPH R01220 Glycine + Tetrahydrofolic acid + NAD <> 5,10-Methylene-THF + Ammonia + Carbon dioxide + NADH + Hydrogen ion R01221 5-Methyltetrahydrofolic acid + NADP <> 5,10-Methylene-THF + NADPH + Hydrogen ion R01224 5,10-Methylene-THF + alpha-Ketoisovaleric acid + Water <> Tetrahydrofolic acid + 2-Dehydropantoate R01226 S-Aminomethyldihydrolipoylprotein + Tetrahydrofolic acid + S-Aminomethyldihydrolipoylprotein <> Dihydrolipoylprotein + 5,10-Methylene-THF + Ammonia R04125 5-Methyltetrahydrofolic acid + NAD <> 5,10-Methylene-THF + NADH + Hydrogen ion R07168 1.5.1.20-RXN 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 dUMP + 5,10-Methylene-THF > 5-Thymidylic acid + Dihydrofolic acid THYMIDYLATESYN-RXN 5,10-Methylene-THF + NADP > 5,10-Methenyltetrahydrofolate + NADPH [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 + NAD(P)(+) > 5,10-Methylene-THF + NAD(P)H 5,10-Methylene-THF + a-Ketoisovaleric acid + Water > Tetrahydrofolic acid + 2-Dehydropantoate 5-Methyltetrahydrofolic acid + NAD + NADP <> 5,10-Methylene-THF + NADH + NADPH + Hydrogen ion R01224 R07168 Dihydrofolic acid + 5-Thymidylic acid + Dihydrofolic acid > 5,10-Methylene-THF + dUMP + 5,10-Methylene-THF PW_R002540 5,10-Methylene-THF + NADPH + Hydrogen ion + 5,10-Methylene-THF + NADPH > 5-Methyltetrahydrofolic acid + NADP + 5-Methyltetrahydrofolic acid PW_R002541 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 5,10-Methenyltetrahydrofolic acid + NADPH + NADPH > 5,10-Methylene-THF + NADP + 5,10-Methylene-THF PW_R002553 a-Ketoisovaleric acid + 5,10-Methylene-THF + Water + 5,10-Methylene-THF > Tetrahydrofolic acid + 2-dehydropantoate + Tetrahydrofolic acid + 2-Dehydropantoate PW_R002999 dUMP + 5 5,10-Methylene-THF <> Dihydrofolic acid +5 5-Thymidylic acid 2 Hydrogen ion + 5 5,10-Methylene-THF + NADH >5 5-Methyltetrahydrofolic acid + NAD alpha-Ketoisovaleric acid + Water + 5 5,10-Methylene-THF + a-Ketoisovaleric acid <>2 2-Dehydropantoate + Tetrahydrofolic acid Glycine + Tetrahydrofolic acid + NAD <>5 5,10-Methylene-THF + Ammonia + Carbon dioxide + NADH + Hydrogen ion dUMP + 5 5,10-Methylene-THF <> Dihydrofolic acid +5 5-Thymidylic acid 2 Hydrogen ion + 5 5,10-Methylene-THF + NADH >5 5-Methyltetrahydrofolic acid + NAD Glycine + Tetrahydrofolic acid + NAD <>5 5,10-Methylene-THF + Ammonia + Carbon dioxide + NADH + Hydrogen ion