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MetaCyc Compound Class: a tetrahydrofolate

Synonyms: tetrahydropteroyl polyglutamate, THF(glu)n, H4PteGlun, a tetrahydrofolate-glutamate, THF, THF polyglutamate

Superclasses: a cofactora prosthetic groupa folate
a vitamina folate
an organic heterocyclic compoundan organic heterobicyclic compounda pteridinea pterina pteroatea folate
an organic heterocyclic compoundan organonitrogen heterocyclic compounda pteridinea pterina pteroatea folate

a tetrahydrofolate compound structure

Child Classes: a tetrahydrofolate derivative (16)

Instances:
tetrahydropteroyl di-L-glutamate,
tetrahydropteroyl mono-L-glutamate,
tetrahydropteroyl penta-L-glutamate,
tetrahydropteroyl tetra-L-glutamate,
tetrahydropteroyl tri-L-glutamate,
tetrahydropteroyl-α-glutamylglutamate

SMILES: C([CH]2(NC1(C(NC(=NC=1NC2)N)=O)))NC3(=CC=C(C(NC(C(=O)[O-])CCC([R])=O)=O)C=C3)

Unification Links: KEGG:C03541, PubChem:25202940

Reactions known to consume the compound:

bacimethrin and bacimethrin pyrophosphate biosynthesis :
CMP + a 5,10-methylene-tetrahydrofolate + H2O → 5-hydroxymethylcytidine 5'-phosphate + a tetrahydrofolate

dimethylsulfoniopropanoate degradation III (demethylation) :
3-(methylthio)propanoate + an N5-methyl-tetrahydrofolate + H+ ← dimethylsulfoniopropanoate + a tetrahydrofolate

folate polyglutamylation :
tetrahydropteroyl-[γ-Glu](n) + L-glutamate + ATP → tetrahydropteroyl-[γ-Glu](n+1) + ADP + phosphate
a tetrahydrofolate + ATP + formate → 10-formyl-tetrahydropteroyl-[γ-Glu](n) + ADP + phosphate

folate transformations I :
L-homocysteine + an N5-methyl-tetrahydrofolate → L-methionine + a tetrahydrofolate
an N10-formyl-tetrahydrofolate + H2O → a tetrahydrofolate + formate + H+
a tetrahydrofolate + ATP + formate → 10-formyl-tetrahydropteroyl-[γ-Glu](n) + ADP + phosphate
a tetrahydrofolate + trimethyl sulfonium ← dimethyl sulfide + an N5-methyl-tetrahydrofolate + H+

folate transformations II :
L-homocysteine + an N5-methyl-tetrahydrofolate → L-methionine + a tetrahydrofolate
a tetrahydrofolate + ATP + formate → 10-formyl-tetrahydropteroyl-[γ-Glu](n) + ADP + phosphate

formaldehyde assimilation I (serine pathway) :
formaldehyde + a tetrahydrofolate → a 5,10-methylene-tetrahydrofolate + H2O

formate assimilation into 5,10-methylenetetrahydrofolate , reductive acetyl coenzyme A pathway :
a tetrahydrofolate + ATP + formate → 10-formyl-tetrahydropteroyl-[γ-Glu](n) + ADP + phosphate

glutamate removal from folates :
tetrahydropteroyl-[γ-Glu](n) + n H2O → n L-glutamate + tetrahydropteroyl mono-L-glutamate

glycine betaine degradation II (mammalian) :
dimethylglycine + 2 an oxidized electron-transfer flavoprotein + a tetrahydrofolate + 3 H+ → sarcosine + a 5,10-methenyltetrahydrofolate + 2 a reduced electron-transfer flavoprotein
sarcosine + 2 an oxidized electron-transfer flavoprotein + a tetrahydrofolate + 3 H+ → glycine + a 5,10-methenyltetrahydrofolate + 2 a reduced electron-transfer flavoprotein

L-histidine degradation III :
a 5-formiminotetrahydrofolate + L-glutamate ← N-formimino-L-glutamate + a tetrahydrofolate

L-methionine biosynthesis I , L-methionine biosynthesis III , L-methionine salvage from L-homocysteine , N10-formyl-tetrahydrofolate biosynthesis :
L-homocysteine + an N5-methyl-tetrahydrofolate → L-methionine + a tetrahydrofolate

polymyxin resistance :
UDP-4-amino-4-deoxy-β-L-arabinopyranose + an N10-formyl-tetrahydrofolate → UDP-4-deoxy-4-formamido-β-L-arabinopyranose + a tetrahydrofolate + H+

purine nucleobases degradation I (anaerobic) , purine nucleobases degradation II (anaerobic) :
an N10-formyl-tetrahydrofolate + H2O → a tetrahydrofolate + formate + H+

pyoverdine I biosynthesis :
N5-hydroxy-L-ornithine + an N10-formyl-tetrahydrofolate → N5-formyl-N5-hydroxy-L-ornithine + a tetrahydrofolate

pyrimidine deoxyribonucleotides de novo biosynthesis III :
dUMP + a 5,10-methylene-tetrahydrofolate + NADPH + H+ → dTMP + a tetrahydrofolate + NADP+

syringate degradation :
syringate + a tetrahydrofolate → 3-O-methylgallate + an N5-methyl-tetrahydrofolate
3-O-methylgallate + a tetrahydrofolate → gallate + an N5-methyl-tetrahydrofolate

vanillin and vanillate degradation I :
vanillate + a tetrahydrofolate → protocatechuate + an N5-methyl-tetrahydrofolate

Not in pathways:
an N10-formyl-tetrahydrofolate + an L-methionyl-[initiator tRNAmet] → a tetrahydrofolate + an N-formyl-L-methionyl-[initiator tRNAmet]

Reactions known to produce the compound:

folate transformations II , N10-formyl-tetrahydrofolate biosynthesis , tetrahydrofolate biosynthesis :
a tetrahydrofolate + NADP+ ← a 7,8-dihydrofolate + NADPH + H+

Reactions known to both consume and produce the compound:

5-aminoimidazole ribonucleotide biosynthesis I , tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate :
an N10-formyl-tetrahydrofolate + N1-(5-phospho-β-D-ribosyl)glycinamide ↔ a tetrahydrofolate + N2-formyl-N1-(5-phospho-β-D-ribosyl)glycinamide + H+

folate polyglutamylation , formaldehyde assimilation I (serine pathway) , glycine betaine degradation I , glycine betaine degradation II (mammalian) , glycine biosynthesis I :
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O

folate transformations I :
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O
glycine + a tetrahydrofolate + NAD+ ↔ a 5,10-methylene-tetrahydrofolate + ammonium + CO2 + NADH

folate transformations II :
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O
glycine + a tetrahydrofolate + NAD+ ↔ a 5,10-methylene-tetrahydrofolate + ammonium + CO2 + NADH

glycine cleavage :
a [glycine-cleavage complex H protein] N6-aminomethyldihydrolipoyl-L-lysine + a tetrahydrofolate ↔ a [glycine-cleavage complex H protein] N6-dihydrolipoyl-L-lysine + a 5,10-methylene-tetrahydrofolate + ammonium

inosine-5'-phosphate biosynthesis I , inosine-5'-phosphate biosynthesis II :
an N10-formyl-tetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide ↔ a tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)-imidazole-4-carboxamide

N10-formyl-tetrahydrofolate biosynthesis :
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O
glycine + a tetrahydrofolate + NAD+ ↔ a 5,10-methylene-tetrahydrofolate + ammonium + CO2 + NADH

phosphopantothenate biosynthesis I :
a 5,10-methylene-tetrahydrofolate + 3-methyl-2-oxobutanoate + H2O ↔ 2-dehydropantoate + a tetrahydrofolate

photorespiration :
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O
glycine + a tetrahydrofolate + NAD+ ↔ a 5,10-methylene-tetrahydrofolate + ammonium + CO2 + NADH

purine nucleobases degradation I (anaerobic) :
a 5-formiminotetrahydrofolate + glycine ↔ N-formimino-glycine + a tetrahydrofolate

purine nucleobases degradation II (anaerobic) :
a 5-formiminotetrahydrofolate + glycine ↔ N-formimino-glycine + a tetrahydrofolate
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O

reductive acetyl coenzyme A pathway :
a tetrahydrofolate + a [methyl-Co(III) corrinoid Fe-S protein] ↔ an N5-methyl-tetrahydrofolate + a [Co(I) corrinoid Fe-S protein] + H+

In Reactions of unknown directionality:

methylthiopropanonate degradation II (demethylation) :
3-(methylthio)propanoate + a tetrahydrofolate = 3-mercaptopropanoate + an N5-methyl-tetrahydrofolate

Not in pathways:
an N10-formyl-tetrahydrofolate + NADP+ + H2O = a tetrahydrofolate + CO2 + NADPH + H+
a 5,10-methylene-tetrahydrofolate + D-alanine + H2O = 2-methylserine + a tetrahydrofolate
dCMP + a 5,10-methylene-tetrahydrofolate + H2O = 2'-deoxy-5-hydroxymethylcytidine 5'-phosphate + a tetrahydrofolate
a 5,10-methylene-tetrahydrofolate + a uracil54 in tRNA + FADH2 = a tetrahydrofolate + a 5-methyluracil54 in tRNA + FAD + H+

Enzymes inhibited by a tetrahydrofolate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: formimidoyltetrahydrofolate cyclodeaminase [Uyeda67a]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: sarcosine oxidase, serine hydroxymethyltransferase

This compound has been characterized as an alternative substrate of the following enzymes: 5,10-methylene-tetrahydrofolate:L-glutamate γ-ligase (ADP-forming)


References

Hanson02: Hanson AD, Gregory JF (2002). "Synthesis and turnover of folates in plants." Curr Opin Plant Biol 5(3);244-9. PMID: 11960743

Jabrin03: Jabrin S, Ravanel S, Gambonnet B, Douce R, Rebeille F (2003). "One-carbon metabolism in plants. Regulation of tetrahydrofolate synthesis during germination and seedling development." Plant Physiol 131(3);1431-9. PMID: 12644692

Lucock: Lucock M (2000). "Folic acid: nutritional biochemistry, molecular biology, and role in disease processes." Mol Genet Metab 71(1-2);121-38. PMID: 11001804

Uyeda67a: Uyeda K, Rabinowitz JC (1967). "Metabolism of formiminoglycine. Formiminotetrahydrofolate cyclodeaminase." J Biol Chem 242(1);24-31. PMID: 6016330


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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