10-Formyltetrahydrofolate

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10-Formyltetrahydrofolate
10-formyl-tetrahydrofolic acid.svg
Names
IUPAC names
(2S)-2-{[4-[(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)
methyl(formyl)amino]benzoyl]amino}pentanedioic acid
Other names
10-CHO-THF
Identifiers
CAS number 2800-34-2
ChemSpider 9 YesY
Jmol-3D images Image
Image
MeSH 10-formyl-tetrahydrofolate
PubChem 10
Properties
C20H23N7O7
Molar mass 473.44 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

10-Formyltetrahydrofolate (10-CHO-THF) is form of tetrahydrofolate that acts as a donor of formyl groups in anabolism. In these reactions 10-CHO-THF is used as a substrate in formyltransferase reactions. This is important in purine biosynthesis, where 10-CHO-THF is a substrate for phosphoribosylaminoimidazolecarboxamide formyltransferase, as well as in the formylation of the methionyl initiator tRNA (fMet-tRNA), when 10-CHO-THF is a substrate for methionyl-tRNA formyltransferase.

Biosynthesis[edit]

10-CHO-THF is produced either by the enzyme methenyltetrahydrofolate cyclohydrolase via the reaction

5,10-methenyltetrahydrofolate + H2O \rightleftharpoons 10-formyltetrahydrofolate

and by the enzyme formate-tetrahydrofolate ligase via the reaction

ATP + formate + tetrahydrofolate \rightleftharpoons ADP + phosphate + 10-formyltetrahydrofolate

It can be converted back into tetrahydrofolate (THF) by formyltetrahydrofolate dehydrogenase or THF and formate by formyltetrahydrofolate deformylase.