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10-Formyltetrahydrofolate

Group of stereoisomers

10-Formyltetrahydrofolate
Names
IUPAC name
(2S)-2-{[4-[(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl(formyl)amino]benzoyl]amino}pentanedioic acid
Other names
10-CHO-THF
10-formylH4folate
N10-formyltetrahydrofolate
Identifiers
3D model (JSmol)
ChemSpider
  • 9  Y
MeSH 10-formyl-tetrahydrofolate
Properties
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  Y N ?)
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.

10-Formyltetrahydrofolate Intro articles: 4
1 Tetrahydrofolic acid
Tetrahydrofolic acid (THFA), or tetrahydrofolate, is a folic acid derivative.More
2 Aldehyde
Aldehydes, which are generally created by removing a hydrogen from an alcohol, are common in organic chemistry; the most well-known is formaldehyde. As they are frequently strongly scented, many fragrances are or contain aldehydes.More
3 Anabolism
Anabolism is the set of metabolic pathways that construct molecules from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catabolism is the breaking-down aspect. Anabolism is usually synonymous with biosynthesis.More
4 Substrate (chemistry)
In chemistry, a substrate is typically the chemical species being observed in a chemical reaction, which reacts with a reagent to generate a product. It can also refer to a surface on which other chemical reactions are performed, or play a supporting role in a variety of spectroscopic and microscopic techniques. In synthetic and organic chemistry, the substrate is the chemical of interest that is being modified. In biochemistry, an enzyme substrate is the material upon which an enzyme acts. When referring to Le Chatelier's principle, the substrate is the reagent whose concentration is changed. The term substrate is highly context-dependent.More

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-Formyltetrahydrofolate Functions articles: 5
1 Purine metabolism
Purine metabolism refers to the metabolic pathways to synthesize and break down purines that are present in many organisms.More
2 Pentose phosphate pathway
The pentose phosphate pathway is a metabolic pathway parallel to glycolysis. It generates NADPH and pentoses as well as ribose 5-phosphate, a precursor for the synthesis of nucleotides. While the pentose phosphate pathway does involve oxidation of glucose, its primary role is anabolic rather than catabolic. The pathway is especially important in red blood cells (erythrocytes).More
3 Phosphoribosylaminoimidazolecarboxamide formyltransferase
In enzymology, a phosphoribosylaminoimidazolecarboxamide formyltransferase, also known by the shorter name AICAR transformylase, is an enzyme that catalyzes the chemical reaction
10-formyltetrahydrofolate + AICAR tetrahydrofolate + FAICAR
More
4 Methionyl-tRNA formyltransferase
In enzymology, a methionyl-tRNA formyltransferase (EC 2.1.2.9) is an enzyme that catalyzes the chemical reaction
10-formyltetrahydrofolate + L-methionyl-tRNAfMet + H2O tetrahydrofolate + N-formylmethionyl-tRNAfMet
More
5 N-Formylmethionine
N-Formylmethionine is a derivative of the amino acid methionine in which a formyl group has been added to the amino group. It is specifically used for initiation of protein synthesis from bacterial and organellar genes, and may be removed post-translationally.More

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.

10-Formyltetrahydrofolate Formation from methenyltetrahydrofolate articles: 6
1 5,10-Methylenetetrahydrofolate
5,10-Methylenetetrahydrofolate (N5,N10-Methylenetetrahydrofolate; 5,10-CH2-THF) is cofactor in several biochemical reactions. It exists in nature as the diastereoisomer [6R]-5,10-methylene-THF.More
2 5,10-Methenyltetrahydrofolate
5,10-Methenyltetrahydrofolate (5,10-CH=THF) is a form of tetrahydrofolate that is an intermediate in metabolism. 5,10-CH=THF is a coenzyme that accepts and donates methenyl (CH=) groups.More
3 Formate
Formate (IUPAC name: methanoate) is the anion derived from formic acid. Its formula is represented in various equivalent ways: HCOO− or CHOO− or HCO2−. It is the product of deprotonation of formic acid. It is the simplest carboxylate anion. A formate (compound) is a salt or ester of formic acid.More
4 Formate–tetrahydrofolate ligase
In enzymology, a formate-tetrahydrofolate ligase is an enzyme that catalyzes the chemical reaction
ATP + formate + tetrahydrofolate ADP + phosphate + 10-formyltetrahydrofolate
More
5 Formyltetrahydrofolate dehydrogenase
In enzymology, a formyltetrahydrofolate dehydrogenase (EC 1.5.1.6) is an enzyme that catalyzes the chemical reaction
10-formyltetrahydrofolate + NADP+ + H2O tetrahydrofolate + CO2 + NADPH + H+
More
6 Formyltetrahydrofolate deformylase
In enzymology, a formyltetrahydrofolate deformylase (EC 3.5.1.10) is an enzyme that catalyzes the chemical reaction
10-formyltetrahydrofolate + H2O formate + tetrahydrofolate
More

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: 1109–1115. doi:10.1021/bi971906t. PMID 9454603.

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