- Functions
- Formation from methenyltetrahydrofolate
- References
| 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
| IUPACName=(2S)-2-
| OtherNames= 10-CHO-THF, 10-formylH4folate
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9
| 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)
| InChIKey = AUFGTPPARQZWDO-UHFFFAOYAK
| SMILES1 = O=C(O)C(NC(=O)c1ccc(cc1)N(C=O)CC3N/C2=C(/N/C(=N\\C2=O)N)NC3)CCC(=O)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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AUFGTPPARQZWDO-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo=2800-34-2
| PubChem=10
| 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
| MeSHName=10-formyl-tetrahydrofolate
|Section2={{Chembox Properties
| Formula=C20H23N7O7
| MolarMass=473.44 g/mol
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
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, 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
The latter is equivalently written:
5,10-methenyltetrahydrofolate + H2O
10-CHO-THF is also produced by the reaction
ATP + formate + tetrahydrofolate
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
2. ^{{cite journal|title=Methenyltetrahydrofolate Cyclohydrolase Is Rate Limiting for the Enzymatic Conversion of 10-Formyltetrahydrofolate to 5,10-Methylenetetrahydrofolate in Bifunctional Dehydrogenase-Cyclohydrolase Enzymes|authors=Peter D. Pawelek, Robert E. MacKenzie|journal=Biochemistry|year=1998|volume=37|pages=1109–1115|doi=10.1021/bi971906t}}
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