メチレンテトラヒドロ葉酸

5,10-methylenetetrahydrofolate

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/03 17:56:13」(JST)

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5,10-Methylenetetrahydrofolate (5,10-CH₂-THF) is the substrate used by the enzyme methylenetetrahydrofolate reductase (MTHFR)^[1]^[2] to generate 5-methyltetrahydrofolate (5-MTHF, or levomefolic acid).

5,10-CH₂-THF can also be used as a coenzyme in the biosynthesis of thymidine. More specifically it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). It also acts as a coenzyme in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase.

References[edit]

^ "Entrez Gene: MTHFR methylenetetrahydrofolate reductase (NAD(P)H)".
^ Födinger M, Hörl WH, Sunder-Plassmann G (2000). "Molecular biology of 5,10-methylenetetrahydrofolate reductase.". J Nephrol 13 (1): 20–33. PMID 10720211.

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English Journal

The relationship between methylenetetrahydrofolate reductase c.677TT genotype and oligozoospermia in infertile male patients living in the Trakya region of Turkey.

Gurkan H1, Tozkır H1, Göncü E1, Ulusal S1, Yazar M1.
Andrologia.Andrologia.2015 Nov;47(9):1068-74. doi: 10.1111/and.12380. Epub 2014 Nov 26.
Methylenetetrahydrofolate reductase (MTHFR), the key enzyme of the folate metabolic pathway, has been reported to be five times more active in the testicles compared to other organs in adult mice. The aim of this study was to investigate the relationship between MTHFR c.677C>T and c.1298A>C po
PMID 25428700

A phase 1 clinical trial of sequential pralatrexate followed by a 48-hour infusion of 5-fluorouracil given every other week in adult patients with solid tumors.

Grem JL1, Kos ME2, Evande RE1, Meza JL3, Schwarz JK1.
Cancer.Cancer.2015 Nov 1;121(21):3862-8. doi: 10.1002/cncr.29504. Epub 2015 Aug 4.
BACKGROUND: Pralatrexate (PDX) is an inhibitor of dihydrofolate reductase that was rationally designed to improve cellular uptake and retention of the drug. Preclinical data have shown synergy with the sequential administration of a dihydrofolate reductase inhibitor followed 24 hours later by 5-fluo
PMID 26242208

Pharmacokinetics and pharmacogenetics of capecitabine and its metabolites following replicate administration of two 500 mg tablet formulations.

Queckenberg C1,2, Erlinghagen V3, Baken BC4, Van Os SH4, Wargenau M5, Kubeš V6, Peroutka R6, Novotný V6, Fuhr U3.
Cancer chemotherapy and pharmacology.Cancer Chemother Pharmacol.2015 Nov;76(5):1081-91. doi: 10.1007/s00280-015-2840-6. Epub 2015 Aug 5.
PURPOSE: To describe concentration versus time profiles of capecitabine and its metabolites 5'-DFUR, 5'-DFCR and 5-FU, depending on tablet formulation and on frequent and/or relevant genetic polymorphisms of cytidine deaminase, dihydropyrimidine dehydrogenase, thymidylate synthase and methylenetetra
PMID 26242222

Japanese Journal

Livedo vasculopathy associated with methylenetetrahydrofolate reductase C677T homozygosity

岸部麻里,Komatsu Shigetsuna,Ishida-Yamamoto Akemi,Iizuka Hajime
The Journal of Dermatology 39(1), 91-94, 2012-1
著者最終原稿版
NAID 120004664148

Effects of Maternal 5,10-Methylenetetrahydrofolate Reductase C677T and A1298C Polymorphisms and Tobacco Smoking on Infant Birth Weight in a Japanese Population

Yila Thamar Ayo,Sasaki Seiko,Miyashita Chihiro,Braimoh Titilola Serifat,Kashino Ikuko,Kobayashi Sumitaka,Okada Emiko,Baba Toshiaki,Yoshioka Eiji,Minakami Hisanori,Endo Toshiaki,Sengoku Kazuo,Kishi Reiko
Journal of Epidemiology 22(2), 91-102, 2012
… Background: Intracellular folate hemostasis depends on the 5,10-methylenetetrahydrofolate reductase (MTHFR) gene. …
NAID 120003974406

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★リンクテーブル★

リンク元	「5,10-メチレンテトラヒドロ葉酸」
拡張検索	「methylenetetrahydrofolate reductase」「5,10-methylenetetrahydrofolate dehydrogenase」「5,10-methylenetetrahydrofolate」

「5,10-メチレンテトラヒドロ葉酸」

5,10-Methylenetetrahydrofolate
	IUPAC name N-[4-(3-amino-1-oxo-1,4,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9H)-yl)benzoyl]-L-glutamic acid
	Other names 5,10-CH2-THF,; MTHF
Identifiers
CAS number	3432-99-3
PubChem	108194
ChemSpider	97272
MeSH	5,10-methylenetetrahydrofolate
ChEBI	CHEBI:20502
ChEMBL	CHEMBL117348
Jmol-3D images	Image 1
	SMILES O=C(O)[C@@H](NC(=O)c1ccc(cc1)N4CC3N(C=2C(=O)/N=C(/N)NC=2NC3)C4)CCC(=O)O ;
	InChI InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12?,13-/m0/s1 ; Key: QYNUQALWYRSVHF-ABLWVSNPSA-N InChI=1/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12?,13-/m0/s1; Key: QYNUQALWYRSVHF-ABLWVSNPBB ;
Properties
Molecular formula	C20H23N7O6
Molar mass	457.44 g/mol
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

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英: 5,10-methylenetetrahydrofolate 5,10-MTHF,methylenetetrahydrofolate MTHF
同: 5,10-メチレン-THF、メチレンテトラヒドロ葉酸
関: 葉酸

「methylenetetrahydrofolate reductase」

　　[★]

メチレンテトラヒドロ葉酸還元酵素、メチレンテトラヒドロ葉酸レダクターゼ

関: 5,10-methylenetetrahydrofolate reductase、MTHFR

5,10-methylenetetrahydrofolate reductase

同: MTHFR

「5,10-methylenetetrahydrofolate dehydrogenase」

　　[★]

5、5,10-メチレンテトラヒドロ葉酸デヒドロゲナーゼ

「5,10-methylenetetrahydrofolate」

　　[★] 5,10-メチレンテトラヒドロ葉酸

[entrez-1] "Entrez Gene: MTHFR methylenetetrahydrofolate reductase (NAD(P)H)".

[pmid10720211-2] Födinger M, Hörl WH, Sunder-Plassmann G (2000). "Molecular biology of 5,10-methylenetetrahydrofolate reductase.". J Nephrol 13 (1): 20–33. PMID 10720211.

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案内

methylenetetrahydrofolate