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 N^10-formyltetrahydrofolate
Identifiers
CAS Number	2800-34-2
3D model (JSmol)	Interactive image Interactive image
ChemSpider	9
MeSH	10-formyl-tetrahydrofolate
PubChem CID	10
InChI InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32) Key: AUFGTPPARQZWDO-UHFFFAOYSA-N InChI=1/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32) Key: AUFGTPPARQZWDO-UHFFFAOYAK
SMILES C1C(NC2=C(N1)NC(=NC2=O)N)CN(C=O)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O O=C(O)C(NC(=O)c1ccc(cc1)N(C=O)CC3N/C2=C(/N/C(=N\C2=O)N)NC3)CCC(=O)O
Properties
Chemical formula	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

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⁺ ${\displaystyle \rightleftharpoons }$ CH₂H₂F + NADH + H⁺

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

CH₂H₂F + H₂O ${\displaystyle \rightleftharpoons }$ CHO-H₄F +

The latter is equivalently written:

5,10-methenyltetrahydrofolate + H₂O ${\displaystyle \rightleftharpoons }$ 10-formyltetrahydrofolate

10-CHO-THF is also produced by the reaction

ATP + formate + tetrahydrofolate ${\displaystyle \rightleftharpoons }$ 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

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.