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-FormylH4 folate N 10 -Formyltetrahydrofolate
Identifiers
ChemSpider
KEGG
MeSH
10-formyl-tetrahydrofolate
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
c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)N(CC2CNc3c(c(=O)nc([nH]3)N)N2)C=O
Properties
C20 H23 N7 O7
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).
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.[ 1]
10-CHO-THF is produced from methylenetetrahydrofolate (CH2 H4 F) via a two step process. The first step generates 5,10-methenyltetrahydrofolate :[ 2]
CH2 H4 F + NAD+
⇌ ⇌ -->
{\displaystyle \rightleftharpoons }
2 H2 F + NADH + H+ In the second step 5,10-methenyltetrahydrofolate undergoes hydrolysis:
CH2 H2 F + H2 O
⇌ ⇌ -->
{\displaystyle \rightleftharpoons }
4 F + The latter is equivalently written:
5,10-methenyltetrahydrofolate + H2 O
⇌ ⇌ -->
{\displaystyle \rightleftharpoons }
10-CHO-THF is also produced by the reaction
ATP + formate + tetrahydrofolate
⇌ ⇌ -->
{\displaystyle \rightleftharpoons }
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
^ Voet, Donald (2016). Fundamentals of Biochemistry: Life at the Molecular Level (5th ed.). Wiley. pp. 1006– 1007. ISBN 978-1-118-91840-1 ^ 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 .
