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10-Formyltetrahydrofolate

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10-Formyltetrahydrofolate
Skeletal formula of 10-formyltetrahydrofolate
Space-filling model of the 10-formyltetrahydrofolate molecule
Names
Preferred IUPAC name (2S)-2-methyl}formamido)benzamido]pentanedioic acid
Other names
  • 10-CHO-THF
  • 10-FormylH4folate
  • N-Formyltetrahydrofolate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
KEGG
MeSH 10-formyl-tetrahydrofolate
PubChem CID
CompTox Dashboard (EPA)
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/s1Key: AUFGTPPARQZWDO-YUZLPWPTSA-N
SMILES
  • c1cc(ccc1C(=O)N(CCC(=O)O)C(=O)O)N(CC2CNc3c(c(=O)nc(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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Formation from methenyltetrahydrofolate

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

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 (4): 1109–1115. doi:10.1021/bi971906t. PMID 9454603.
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