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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. To be specific, it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). It also acts as a cofactor in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase.

MTHFR metabolism: folate cycle, methionine cycle, trans-sulfuration and hyperhomocysteinemia. 5-MTHF: 5-methyltetrahydrofolate; 5,10-methyltetrahydrofolate; BAX: Bcl-2-associated X protein; BHMT: betaine-homocysteine S-methyltransferase; CBS: cystathionine beta synthase; CGL: cystathionine gamma-lyase; DHF: dihydrofolate (vitamin B9); DMG: dimethylglycine; dTMP: thymidine monophosphate; dUMP: deoxyuridine monophosphate; FAD⁺ flavine adenine dicucleotide; FTHF: 10-formyltetrahydrofolate; MS: methionine synthase; MTHFR: mehtylenetetrahydrofolate reductase; SAH: S-adenosyl-L-homocysteine; SAME: S-adenosyl-L-methionine; THF: tetrahydrofolate.

References

^ "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

Human and Plasmodium serine hydroxymethyltransferases differ in rate-limiting steps and pH-dependent substrate inhibition behavior.

Amornwatcharapong W1, Maenpuen S2, Chitnumsub P3, Leartsakulpanich U4, Chaiyen P5.
Archives of biochemistry and biophysics.Arch Biochem Biophys.2017 Sep 15;630:91-100. doi: 10.1016/j.abb.2017.07.017. Epub 2017 Jul 29.
PMID 28760597

One-carbon metabolites and telomere length in a prospective and randomized study of B- and/or D-vitamin supplementation.

Pusceddu I1, Herrmann M2, Kirsch SH1, Werner C3, Hübner U1, Bodis M1, Laufs U3, Widmann T4, Wagenpfeil S5, Geisel J1, Herrmann W6.
European journal of nutrition.Eur J Nutr.2017 Aug;56(5):1887-1898. doi: 10.1007/s00394-016-1231-z. Epub 2016 Jul 5.
PMID 27379829

A systematic review of the risks factors associated with the onset and natural progression of spina bifida.

Donnan J1, Walsh S2, Sikora L3, Morrissey A2, Collins K2, MacDonald D2.
Neurotoxicology.Neurotoxicology.2017 Jul;61:20-31. doi: 10.1016/j.neuro.2016.03.008. Epub 2016 Mar 19.
PMID 27000518

Japanese Journal

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, 2012-03-01
… Background: Intracellular folate hemostasis depends on the 5,10-methylenetetrahydrofolate reductase (MTHFR) gene. … Because 5,10-MTHFR 677TT homozygosity and tobacco smoking are associated with low folate status, we tested the hypothesis that smoking in mothers with 5,10-MTHFR C677T or A1298C polymorphisms would be independently associated with lower birth weight among their offspring. …
NAID 10030213303

5,10-Methylenetetrahydrofolate reductase deficiency with progressive polyneuropathy in an infant

TSUJI Megumi,TAKAGI Atsushi,SAMESHIMA Kiyoko,IAI Mizue,YAMASHITA Sumimasa,SHINBO Hiroko,FURUYA Noritaka,KUROSAWA Kenji,OSAKA Hitoshi
Brain & development 33(6), 521-524, 2011-06-06
NAID 10029562192

MATERNAL A1298C POLYMORPHISM OF THE 5,10-METHYLENETETRAHYDROFOLATE REDUCTASE IS ASSOCIATED TO OCCURRENCE OF CLEFT PALATE ONLY IN MONGOLIANS

TSERENKHAND TSOOJ,LKHAGVA-OCHIR ERKHEMBAATAR,YOSHIDA WAKA,ARIUNTUUL GARIDKHUU,LKHAGVASUREN TSERENKHUU,ERKHEMBAATAR TUDEVDORI,FURUKAWA HIROO,FUJIWARA KUMIKO,NIIMI TERUYUKI,MINAMI KATSUHIRO,SUZUKI SATOSHI,GOTO TAKAHIRO,KOSHIJI CHIKAKO,MAEDA HATSUHIKO,NATSUME NAGATO
Aichi-Gakuin dental science 22, 25-33, 2009-12-30
NAID 10031126385

Related Pictures

★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	「5,10-methylenetetrahydrofolate dehydrogenase」
関連記事	「methylenetetrahydrofolate」

「5,10-メチレンテトラヒドロ葉酸」

5,10-Methylenetetrahydrofolate
Names
	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
ChEBI	CHEBI:20502
ChEMBL	ChEMBL117348
ChemSpider	97272
Jmol 3D model	Interactive image
MeSH	5,10-methylenetetrahydrofolate
PubChem	108194
	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 ;
	SMILES O=C(O)[C@@H](NC(=O)c1ccc(cc1)N4CC3N(C=2C(=O)/N=C(/N)NC=2NC3)C4)CCC(=O)O ;
Properties
Chemical formula	C20H23N7O6
Molar mass	457.44 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

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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

「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

「methylenetetrahydrofolate」

　　[★]

メチレンテトラヒドロ葉酸

5,10-methylenetetrahydrofolate

[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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5,10-methylenetetrahydrofolate