10-Formyltetrahydrofolate

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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, 10-formylH4folate
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.

Functions[edit]

Two equivalents of 10-CHO-THF are required in purine biosynthesis, where 10-CHO-THF is a substrate for phosphoribosylaminoimidazolecarboxamide formyltransferase.

10-CHO-THF is required for the formylation of methionyl-tRNA formyltransferase to give fMet-tRNA.[1]

Formation from methenyltetrahydrofolate[edit]

10-CHO-THF is produced from methylenetetrahydrofolate (CH2H4F) via a two step process. The first step generates 5,10-methenyltetrahydrofolate:[2]

CH2H4F + NAD+ CH2H2F + NADH + H+

In the second step 5,10-methenyltetrahydrofolate undergoes hydrolysis:

CH2H2F + H2O CHO-H2F +

The latter is equivalently written:

5,10-methenyltetrahydrofolate + H2O 10-formyltetrahydrofolate

10-CHO-THF is also produced by the reaction

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

This reaction is catalyzed by formate-tetrahydrofolate ligase.

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

References[edit]

  1. ^ Voet, Donald (2016). Fundamentals of Biochemistry: Life at the Molecular Level (5th ed.). Wiley. pp. 1006–1007. ISBN 978-1-118-91840-1.
  2. ^ Peter D. Pawelek, Robert E. MacKenzie (1998). "Methenyltetrahydrofolate Cyclohydrolase Is Rate Limiting for the Enzymatic Conversion of 10-Formyltetrahydrofolate to 5,10-Methylenetetrahydrofolate in Bifunctional Dehydrogenase-Cyclohydrolase Enzymes". Biochemistry. 37: 1109–1115. doi:10.1021/bi971906t.