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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/10/20 15:23:19」(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

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 尿酸のバランス uric acid balance
2. 出産時の臍帯血酸塩基分析 umbilical cord blood acid base analysis at delivery
3. ポルフィリン症：概要 porphyrias an overview
4. 妊娠中の葉酸補充 folic acid supplementation in pregnancy
5. 疾患予防におけるビタミン補給 vitamin supplementation in disease prevention

English Journal

Relative bioavailability of folate from the traditional food plant Moringa oleifera L. as evaluated in a rat model.

Saini RK1, Manoj P2, Shetty NP2, Srinivasan K3, Giridhar P2.
Journal of food science and technology.J Food Sci Technol.2016 Jan;53(1):511-20. doi: 10.1007/s13197-015-1828-x. Epub 2015 Sep 7.
Moringa oleifera is an affordable and rich source of dietary folate. Quantification of folate by HPLC showed that 5-formyl-5,6,7,8-tetrahydrofolic acid (502.1 μg/100 g DW) and 5,6,7,8-tetrahydrofolic acid (223.9 μg/100 g DW) as the most dominant forms of folate in M. oleifera leaves. The bioav
PMID 26787970

Four Components of the Conjugated Redox System in Organisms: Carbon, Nitrogen, Sulfur, Oxygen.

Tereshina EV1, Laskavy VN, Ivanenko SI.
Biochemistry. Biokhimii︠a︡.Biochemistry (Mosc).2015 Sep;80(9):1186-200. doi: 10.1134/S0006297915090096.
C1 compounds participate in various metabolic processes and regulations including DNA methylation. Formaldehyde (FA), a product of methyl group oxidation, is highly cytotoxic. In the cell, there are two pathways of its utilization: assimilation and oxidation. Formaldehyde displays cytotoxicity, and
PMID 26555471

Structures of the hydrolase domain of zebrafish 10-formyltetrahydrofolate dehydrogenase and its complexes reveal a complete set of key residues for hydrolysis and product inhibition.

Lin CC1, Chuankhayan P1, Chang WN2, Kao TT2, Guan HH1, Fun HK3, Nakagawa A4, Fu TF2, Chen CJ1.
Acta crystallographica. Section D, Biological crystallography.Acta Crystallogr D Biol Crystallogr.2015 Apr;71(Pt 4):1006-21. doi: 10.1107/S1399004715002928. Epub 2015 Mar 27.
10-Formyltetrahydrofolate dehydrogenase (FDH), which is composed of a small N-terminal domain (Nt-FDH) and a large C-terminal domain, is an abundant folate enzyme in the liver and converts 10-formyltetrahydrofolate (10-FTHF) to tetrahydrofolate (THF) and CO2. Nt-FDH alone possesses a hydrolase activ
PMID 25849409

Japanese Journal

Determination of Folate Derivatives in Rat Tissues during Folate Deficiency

Nakata Rieko
Journal of nutritional science and vitaminology 46(5), 215-221, 2000-10-01
… 5, 6, 7, 8-Tetrahydrofolic acid was the major folate derivative in the liver, kidney, spleen and brain. … The level of 5, 6, 7, 8-tetrahydrofolic acid in the brain did not change during folate deficiency, but it significantly decreased in the liver, kidney and spleen. …
NAID 10010804460

豚血漿中より精製した高親和性葉酸結合蛋白の葉酸化合物に対する結合特性

夏堀雅宏,岡田真紀,井田龍 [他],佐々木一昭,下田実,小久江栄一
The journal of veterinary medical science 61(7), 743-748, 1999-07-25
豚血漿中より高親和性葉酸結合蛋白(HFBP)をアフィニティクロマトグラフィにより精製し, 豚血漿中の代表的葉酸化合物であるテトラヒドロ葉酸(THF), N^5-メチルテトラヒドロ葉酸(5MF)および酸化型葉酸(FA)との結合特性を明らかにした. 葉酸結合蛋白は精製により, 血漿の約2,000倍濃縮され, 蛋白1mgあたりの結合容量は1.4nmolとなった. 葉酸化合物(FA, THF, 5MF)の …
NAID 110003920169

EFFECTS OF LEVOFOLINATE CALCIUM ON SUBACUTE INTRAVENOUS TOXICITY OF 5-FLUOROURACIL IN RATS

村上善紀,Fujii Hisako,Ichimura Akitoshi [他],MURATA Akiko,YAMASHITA Noriaki,TAKAGI Hidetoshi,TAUCHI Kiyonori
Journal of toxicological sciences 23(Supplement I), 11-29, 1998-05-09
… In monitoring of blood drug concentrations of 1-LV, 5-methyl tetrahydrofolic acid, a metabolite of 1-LV, and 5-FU after the 1st and 14th dosings, there was no apparent difference between 5-FU alone and 5-FU combined with 1-LV in C_<max> …
NAID 110001806147

Related Pictures

★リンクテーブル★

リンク元	「テトラヒドロ葉酸」
拡張検索	「N5-formyltetrahydrofolic acid」

「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

　　[★]

英: tetrahydrofolate THF, tetrahydrofolic acid THFA H4FA
関: メチルTHF、活性C1単位、葉酸、プテリジン

補因子として働き、C₁単位を転移する
セリン→グリシン (セリンヒドロキシメチルトランスフェラーゼ)
グリシン開裂反応
ヒスチジン分解
ホモシステインからのメチオニン合成
チミンヌクレオチドの合成

dUMP→dTMP

IMPの合成

IMPの合成(IMPからはAMP, GMPができる)

「N5-formyltetrahydrofolic acid」

　　[★] N5-ホルミルテトラヒドロ葉酸

[1] 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.

匿名

検索

案内

案内

tetrahydrofolic acid