10-Formyltetrahydrofolate

{{chembox

| Verifiedfields = changed

| verifiedrevid = 477208698

| ImageFile=10-formyl-tetrahydrofolic acid.svg

| ImageSize=260

| ImageAlt = Skeletal formula of 10-formyltetrahydrofolate

| ImageFile1 = 10-Formyltetrahydrofolate-3D-spacefill.png

| ImageSize1 = 250

| ImageAlt1 = Space-filling model of the 10-formyltetrahydrofolate molecule

| PIN=(2S)-2-[4-(N-{[(6Ξ)-2-Amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}formamido)benzamido]pentanedioic acid

| OtherNames= {{ubl|10-CHO-THF|10-FormylH₄folate|N¹⁰-Formyltetrahydrofolate}}

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 109092

| SMILES = c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)N(CC2CNc3c(c(=O)nc([nH]3)N)N2)C=O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = AUFGTPPARQZWDO-YUZLPWPTSA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo=2800-34-2

| PubChem=135450591

| KEGG=C00234

| MeSHName=10-formyl-tetrahydrofolate

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|Section2={{Chembox Properties

| Formula=C₂₀H₂₃N₇O₇

| MolarMass=473.44 g/mol

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|Section3={{Chembox Hazards

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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.{{cite book|last1=Voet|first1=Donald|title=Fundamentals of Biochemistry: Life at the Molecular Level|date=2016|publisher=Wiley|isbn=978-1-118-91840-1|pages=1006–1007|edition=5th}}

Formation from methenyltetrahydrofolate

10-CHO-THF is produced from methylenetetrahydrofolate (CH₂H₄F) via a two step process. The first step generates 5,10-methenyltetrahydrofolate:{{cite journal|title=Methenyltetrahydrofolate Cyclohydrolase Is Rate Limiting for the Enzymatic Conversion of 10-Formyltetrahydrofolate to 5,10-Methylenetetrahydrofolate in Bifunctional Dehydrogenase-Cyclohydrolase Enzymes|author1=Peter D. Pawelek |author2=Robert E. MacKenzie|journal=Biochemistry|year=1998|volume=37|issue=4 |pages=1109–1115|doi=10.1021/bi971906t|pmid=9454603}}

:CH₂H₄F + NAD⁺ $\rightleftharpoons$ CH₂H₂F + NADH + H⁺

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

:CH₂H₂F + H₂O $\rightleftharpoons$ CHO-H₄F +

The latter is equivalently written:

:5,10-methenyltetrahydrofolate + H₂O $\rightleftharpoons$ 10-formyltetrahydrofolate

10-CHO-THF is also produced by the reaction

:ATP + formate + tetrahydrofolate $\rightleftharpoons$ 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

Category:Folates

Category:Coenzymes