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Tetrahydrofolic acid

 
Wikipedia: Tetrahydrofolic acid
Tetrahydrofolic acid
Tetrahydrofolic acid.svg
Identifiers
CAS number 29347-89-5
PubChem 1129
MeSH 5,6,7,8-tetrahydrofolic+acid
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, 100 kPa)
Infobox references

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

Metabolism

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 in bacteria, an enzyme without function in humans. This makes it a useful target for sulfonamide antibiotics, which compete with the PABA precursor.

Functions

It is a coenzyme 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.

Tetrahydrofolic acid is reduced by the drug methotrexate, which is used to impair nucleotide synthesis. This drug is a potent chemotherapy and anti rheumatic.

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. ^ HISTAMINE FORMATION IN GUINEA-PIGS, W.DAWSON, D.V.MAUDSLEY, G.B.WEST, May 1965, http://jp.physoc.org/content/181/4/801.full.pdf

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