Tetrahydrofolic acid

Structural formula
General
Surname	Tetrahydrofolic acid
other names	H 4 folate FH 4 Coenzyme F N - [(2 S , 6 S ) -5,6,7,8-tetrahydropteroyl] - L -glutamic acid 2 - ((4 - ((2-amino-4-oxo-5,6,7,8-tetrahydro-1 H pteridin-6-yl) methylamino) benzoyl) amino) pentanedioic acid
Molecular formula	C 19 H 23 N 7 O 6
External identifiers / databases
CAS number unknown [(2 S , 6 S ) isomer] 29347-89-5 [unspecified] PubChem 5460413 DrugBank DB02031 Wikidata Q27098158
properties
Molar mass	445.43 g · mol -1
Physical state	firmly
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tetrahydrofolic acid ( H ₄ folate , FH ₄ ), and coenzyme Q , is a biochemical derivative of folic acid ( vitamin B9 ) and acts - linked to a polyglutamic - in the metabolism of all living things as important methyl groups - donor .

Biological importance

Tetrahydrofolic acid and its derivatives are of particular importance in amino acid , pyrimidine and purine metabolism and in homoacetate fermentation . It is required to detoxify formic acid , which is formed from methanol .

Biosynthesis and transport

FH _{4 is produced} biosynthetically from FH ₂ , which is itself produced from folic acid . Both reactions are catalyzed by the enzyme dihydrofolate reductase . Substances that inhibit this enzyme in its function, such as B. Methotrexate ( antimetabolite ) act as cell toxins .

The site of action of FH ₄ is in the cytosol and in the mitochondria of cells. In order to initially transfer FH ₄ from the blood plasma to the cytosol, the cell produces the transport protein folate transporter 1 , which catalyzes the introduction and discharge. To get inside the mitochondrion, there is also the mitochondrial folate transporter .

Reactions as a substrate

FH ₂ , FH ₄ and its derivatives are prevented from being released by binding to polyglutamic acid ( polyglutamate ) and thus stored in the cytosol and the mitochondria of the cells. Only in this form can many of the carbon-transferring reactions take place. The enzyme folyl polyglutamate synthetase is required for the binding of FH ₂ and FH ₄ to polyglutamate .

A number of derived substances are produced from FH ₄ polyglutamate, which act as carbon carriers in important metabolic pathways. Most of the time, FH ₄ polyglutamate remains after the reaction and is reused.

• 10-formyl-FH ₄ -polyglutamate is a reaction partner in the biosynthesis of IMP and methionine . It is made from FH ₄ polyglutamate using the multifunctional enzyme C1-THF synthase .
• Formyl-FH ₄ -PG is converted into 5,10-methylene-FH ₄ -polyglutamate in two steps using the same enzyme . This takes part in the biosynthesis of TMP and in the mutual conversion of glycine to serine .
• The latter substance, in turn, is converted with methylene tetrahydrofolate reductase or with ferredoxin to 5-methyl-FH ₄ -polyglutamate, which methylates homocysteine to methionine and plays a role as a methyl carrier in bacterial methane formation .

Web links

Wiktionary: Tetrahydrofolic acid  - explanations of meanings, word origins, synonyms, translations

Wikibooks: Biochemistry and Pathobiochemistry: Folate Metabolism  - Learning and Teaching Materials

Individual evidence

1. ↑ External identifiers or database links for tetrahydrofolic acid (unspecified) : CAS number: 29347-89-5, PubChem : 1129 , Wikidata : Q168453 .
2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
3. ↑ ^{a b} Metabolism of folate and pterines. Reactome, accessed May 11, 2020 . 
4. ↑ Methylation of Corrinoid  Reaction - R02289 in the Kyoto Encyclopedia of Genes and Genomes .