10-Formyltetrahydrofolate

10-Formyltetrahydrofolate
Skeletal formula of 10-formyltetrahydrofolate
Space-filling model of the 10-formyltetrahydrofolate molecule
Names
IUPAC name
(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
3D model (JSmol)
ChemSpider
MeSH 10-formyl-tetrahydrofolate
Properties
C20H23N7O7
Molar mass 473.44 g/mol
Except where otherwise noted, data are 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 a 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.[1]

Biosynthesis

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

5,10-methenyltetrahydrofolate + H2O 10-formyltetrahydrofolate

or by the enzyme formate-tetrahydrofolate ligase via the reaction

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

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

References

  1. ↑ Voet, Donald (2016). Fundamentals of Biochemistry: Life at the Molecular Level (5th ed.). Wiley. pp. 1006–1007. ISBN 978-1-118-91840-1.


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