同: THF

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/01 22:55:18」(JST)

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Tetrahydrofolic acid, or tetrahydrofolate, is a folic acid derivative.

Metabolism

Synthesis pathway of tetrahydrofolic acid (click to enlarge).

Human synthesis

It is produced from dihydrofolic acid by dihydrofolate reductase. This reaction is inhibited by methotrexate.

It is converted into 5,10-methylenetetrahydrofolate by serine hydroxymethyltransferase.

Bacterial synthesis

Many bacteria use dihydropteroate synthetase to produce dihydropteroate, a molecule without function in humans. This makes it a useful target for sulfonamide antibiotics, which compete with the PABA precursor.

Pathway of tetrahydrofolate and antimetabolites

Functions

It is a cofactor in many reactions, especially in the metabolism of amino acids and nucleic acids. It acts as a donor of a group with one carbon atom. It gets this carbon atom by sequestering formaldehyde produced in other processes. A shortage in THF can cause megaloblastic anemia.

Methotrexate acts on dihydrofolate reductase, like pyrimethamine or trimethoprim, as an inhibitor and thus reduces the amount of tetrahydrofolate made. This may result in megaloblastic anemia.

Tetrahydrofolic acid is involved in the conversion of formiminoglutamic acid to glutamic acid; this may reduce the amount of histidine available for decarboxylation and protein synthesis, and hence the urinary histamine and formiminoglutamic acid may be decreased.^[1]

Dihydrofolic acid
5,10-Methylenetetrahydrofolate

References

^ Dawson W, Maudsley DV, West GB (December 1965). "Histamine formation in guinea-pigs". J. Physiol. (Lond.) 181 (4): 801–9. doi:10.1113/jphysiol.1965.sp007798. PMC 1357684. PMID 5881255.

External links

Tetrahydrofolate bound to proteins in the PDB

UpToDate Contents

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English Journal

Bioequivalence Evaluation of a Folate-Supplemented Oral Contraceptive Containing Ethinylestradiol/Drospirenone/Levomefolate Calcium versus Ethinylestradiol/Drospirenone and Levomefolate Calcium Alone.

Wiesinger H, Eydeler U, Richard F, Trummer D, Blode H, Rohde B, Diefenbach K.SourceBayer HealthCare Pharmaceuticals, Berlin, Germany.
Clinical drug investigation.Clin Drug Investig.2012 Oct 1;32(10):673-84. doi: 10.2165/11635280-000000000-00000.
Background: Neural tube defects (NTDs) are congenital malformations that occur during early embryonic development. Suboptimal maternal folate status is a well-known risk factor for the occurrence of NTDs, and periconceptional folic acid supplementation has been shown to reduce the risk of NTDs. Fola
PMID 22909145

Comparative genomics guided discovery of two missing archaeal enzyme families involved in the biosynthesis of the pterin moiety of methanopterin and tetrahydrofolate.

De Crecy-Lagard V, Phillips G, Grochowski LL, El Yacoubi B, Jenney F, Adams MW, Murzin AG, White RH.AbstractC-1 carriers are essential cofactors in all domains of life, and in Archaea these can be derivatives of methanopterin (H4-MPT) or tetrahydrofolate (H4-folate). Their synthesis requires 6-hydroxymethyl-7,8-dihydropterin diphosphate (6-HMDP) as the precursor but the nature of pathways that lead to its formation were unknown until the recent discovery of the GTP cyclohydrolase IB/MptA family that catalyzes the first step, the conversion of GTP to dihydroneopterin 2',3'-cyclic phosphate or 7,8-dihydroneopterin triphosphate [El Yacoubi, B., et al. (2006, J. Biol. Chem., 281, 37586-37593) and Grochowski et al. (2007, Biochemistry 46, 6658-6667]. Using a combination of comparative genomics analyses, heterologous complementation tests, and in vitro assays, we show that the archaeal protein families COG2098 and COG1634 specify two of the missing 6-HMDP synthesis enzymes. Members of the COG2098 family catalyze the formation of 6-hydroxymethyl-7,8-dihydropterin from 7,8-dihydroneopterin while members of the COG1634 family catalyze the formation of 6-HMDP from 6-hydroxymethyl-7,8-dihydropterin. The discovery of these "missing genes" " solves a long-standing mystery and provides novel examples of convergent evolutions were proteins of dissimilar architectures perform the same biochemical function.
ACS chemical biology.ACS Chem Biol.2012 Aug 29. [Epub ahead of print]
C-1 carriers are essential cofactors in all domains of life, and in Archaea these can be derivatives of methanopterin (H4-MPT) or tetrahydrofolate (H4-folate). Their synthesis requires 6-hydroxymethyl-7,8-dihydropterin diphosphate (6-HMDP) as the precursor but the nature of pathways that lead to its
PMID 22931285

Japanese Journal

Frequency of Genetic Mutations Associated with Thromboembolism in the Western Black Sea Region

Tug Esra,Aydin Hatip,Kaplan Ebru,Dogruer Dilek
Internal Medicine 50(1), 17-21, 2011
Objective We aimed to determine the prevalences of important genetic causes of thromboembolism for the first time in the western Black Sea Region of Turkey. Patients and Methods One hundred and eighty …
NAID 130000413192

Different histological types of non-small cell lung cancer have distinct folate and DNA methylation levels

JIN MingJi,KAWAKAMI Kazuyuki,FUKUI Yousuke,TSUKIOKA Sayaka,ODA Makoto,WATANABE Go,TAKECHI Teiji,OKA Toshinori,MINAMOTO Toshinari
Cancer science 100(12), 2325-2330, 2009-12-10
… Folate concentrations were determined as the sum of 5,10-methylenetetrahydrofolate and tetrahydrofolate. …
NAID 10027198108

Related Pictures

★リンクテーブル★

リンク元	「テトラヒドロ葉酸」「プテリジン」「THF」
拡張検索	「5-methyltetrahydrofolate-homocysteine S-methyltransferase」「5,10-methylenetetrahydrofolate dehydrogenase」「methenyltetrahydrofolate cyclohydrolase」「5,10-methylenetetrahydrofolate」「methyltetrahydrofolate」

「テトラヒドロ葉酸」

Tetrahydrofolic acid
Names
	IUPAC name (2S)-2-{[4-({[(6R)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
Identifiers
CAS Registry Number	135-16-0
ChEBI	CHEBI:20506
ChemSpider	82572
DrugBank	DB00116
	InChI InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1 ; Key: MSTNYGQPCMXVAQ-KIYNQFGBSA-N ; InChI=1/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1; Key: MSTNYGQPCMXVAQ-KIYNQFGBBC ;
IUPHAR/BPS	4675
Jmol-3D images	Image
KEGG	C00101
MeSH	5,6,7,8-tetrahydrofolic+acid
PubChem	91443
	SMILES O=C(O)[C@@H](NC(=O)c1ccc(cc1)NCC3N/C2=C(/N/C(=N\C2=O)N)NC3)CCC(=O)O ;
Properties
Chemical formula	C19H23N7O6
Molar mass	445.43 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references