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Open Access Articles- Top Results for Tetrahydrofolic acid

Tetrahydrofolic acid

Tetrahydrofolic acid
Skeletal formula of tetrahydrofolic acid
Space-filling model of the tetrahydrofolic acid molecule
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IUPAC name
(2S)-2-{[4-({[(6R)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
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135-16-0 7pxN
ChEBI CHEBI:20506 7pxY
ChemSpider 82572 7pxY
DrugBank DB00116 7pxY
Jmol-3D images Image
KEGG C00101 7pxY
MeSH 5,6,7,8-tetrahydrofolic+acid
PubChem Template:Chembox PubChem/format
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C19H23N7O6
Molar mass 445.43 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 14pxN verify (what is10pxY/10pxN?)
Infobox references

Tetrahydrofolic acid, or tetrahydrofolate, is a folic acid derivative.

Metabolism

File:THFsynthesispathway.png
Synthesis pathway of tetrahydrofolic acid (click to enlarge).

Human synthesis

It is produced from dihydrofolic acid by dihydrofolate reductase. This reaction is inhibited by methotrexate.

It is converted into 5,10-methylenetetrahydrofolate by serine hydroxymethyltransferase.

Bacterial synthesis

Many bacteria use dihydropteroate synthetase to produce dihydropteroate, a molecule without function in humans. This makes it a useful target for sulfonamide antibiotics, which compete with the PABA precursor.

File:Pathway of tetrahydrofolate and antimetabolites.pdf
Pathway of tetrahydrofolate and antimetabolites

Functions

It is a cofactor in many reactions, especially in the metabolism of amino acids and nucleic acids. It acts as a donor of a group with one carbon atom. It gets this carbon atom by sequestering formaldehyde produced in other processes. A shortage in THF can cause megaloblastic anemia.

Methotrexate acts on dihydrofolate reductase, like pyrimethamine or trimethoprim, as an inhibitor and thus reduces the amount of tetrahydrofolate made. This may result in megaloblastic anemia.

Tetrahydrofolic acid is involved in the conversion of formiminoglutamic acid to glutamic acid; this may reduce the amount of histidine available for decarboxylation and protein synthesis, and hence the urinary histamine and formiminoglutamic acid may be decreased.[1]

References

  1. ^ Dawson W, Maudsley DV, West GB (December 1965). "Histamine formation in guinea-pigs". J. Physiol. (Lond.) 181 (4): 801–9. PMC 1357684. PMID 5881255. doi:10.1113/jphysiol.1965.sp007798. 

External links

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