Tetrahydrofolic acid

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Tetrahydrofolic acid
Tetrahydrofolic acid.svg
Identifiers
CAS number 135-16-0 N
PubChem 91443
ChemSpider 82572 YesY
DrugBank DB00116
KEGG C00101 YesY
MeSH 5,6,7,8-tetrahydrofolic+acid
ChEBI CHEBI:20506 YesY
Jmol-3D images Image 1
Properties
Molecular formula C19H23N7O6
Molar mass 445.43 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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

Metabolism[edit]

Synthesis pathway of tetrahydrofolic acid (click to enlarge).

Human synthesis[edit]

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[edit]

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.

Pathway of tetrahydrofolate and antimetabolites

Functions[edit]

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[edit]

  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. 

External links[edit]