10-Formyltetrahydrofolate

10-Formyltetrahydrofolate

Names
Preferred IUPAC name (2S)-2-[4-(N-{[(6Ξ)-2-Amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}formamido)benzamido]pentanedioic acid
Other names 10-CHO-THF 10-FormylH4folate N10-Formyltetrahydrofolate
Identifiers
CAS Number	2800-34-2 N
3D model (JSmol)	Interactive image
ChemSpider	109092 Y
KEGG	C00234
MeSH	10-formyl-tetrahydrofolate
PubChem CID	135450591
CompTox Dashboard (EPA)	DTXSID60903987
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)/t11?,13-/m0/s1 Y Key: AUFGTPPARQZWDO-YUZLPWPTSA-N Y
SMILES c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)N(CC2CNc3c(c(=O)nc([nH]3)N)N2)C=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). N verify (what is YN ?) 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

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

This page was last edited on 31 July 2023, at 17:07