10-Formyltetrahydrofolate

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.

10-Formyltetrahydrofolate
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
N10-formyltetrahydrofolate
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).
N verify (what is YN ?)
Infobox references

Functions

Two equivalents of 10-CHO-THF are required in purine biosynthesis through the pentose phosphate pathway, 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

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-H4F +

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.

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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.
  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. PMID 9454603.
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