グルタル酸、グルタル酸エステル、(グルタン酸のエステルもしくは塩類を指す)ルタラート

関: glutaric acid

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/11/15 11:23:42」(JST)

wiki en

Glutaric acid is the organic compound with the formula C₃H₆(COOH)₂ . Although the related "linear" dicarboxylic acids adipic and succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50%.

Preparation

Glutaric acid can be prepared by the ring-opening of butyrolactone with potassium cyanide to give the mixed potassium carboxylate-nitrile that is hydrolyzed to the diacid.^[1] Alternatively hydrolysis, followed by oxidation of dihydropyran gives glutaric acid. It can also be prepared from reacting 1,3-dibromopropane with sodium or potassium cyanide to obtain the dinitrile, followed by hydrolysis.

Uses

1,5-Pentanediol, a common plasticizer and precursor to polyesters is manufactured by hydrogenation of glutaric acid and its derivatives.^[2]

Glutaric acid itself has been used in the production of polymers such as polyester polyols, polyamides. The odd number of carbon atoms (i.e. 5) is useful in decreasing polymer elasticity.^{[citation needed]}

References

^ G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan (1963), "Glutaric Acid and Glutaramide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0496; Coll. Vol. 4: 496
^ Peter Werle and Marcus Morawietz "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry: 2002, Wiley-VCH: Weinheim. DOI 10.1002/14356007.a01_305

External links

Calculator: Water and solute activities in aqueous glutaric acid

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English Journal

Compartmentation of metabolism of the C12-, C9-, and C5-n-dicarboxylates in rat liver, investigated by mass isotopomer analysis: Anaplerosis from dodecanedioate.

Jin Z1, Bian F1, Tomcik K1, Kelleher JK2, Zhang GF3, Brunengraber H4.
The Journal of biological chemistry.J Biol Chem.2015 Jun 12. pii: jbc.M115.651737. [Epub ahead of print]
We investigated the compartmentation of the catabolism of dodecanedioate (DODA), azelate and glutarate in perfused rat livers, using a combination of metabolomics and mass isotopomer analyses. Livers were perfused with recirculating or nonrecirculating buffer containing one fully 13C-labeled dicarbo
PMID 26070565

Experimental Correlation of Substrate Position with Reaction Outcome in the Aliphatic Halogenase, SyrB2.

Martinie RJ1, Livada J1, Chang WC1, Green MT1, Krebs C1, Bollinger JM Jr1, Silakov A1.
Journal of the American Chemical Society.J Am Chem Soc.2015 Jun 3;137(21):6912-9. doi: 10.1021/jacs.5b03370. Epub 2015 May 19.
The iron(II)- and 2-(oxo)glutarate-dependent (Fe/2OG) oxygenases catalyze an array of challenging transformations, but how individual members of the enzyme family direct different outcomes is poorly understood. The Fe/2OG halogenase, SyrB2, chlorinates C4 of its native substrate, l-threonine appende
PMID 25965587

DdrO is an essential protein that regulates the radiation desiccation response and the apoptotic-like cell death in the radioresistant Deinococcus radiodurans bacterium.

Devigne A1, Ithurbide S1, Bouthier de la Tour C1, Passot F1, Mathieu M1, Sommer S1, Servant P1.
Molecular microbiology.Mol Microbiol.2015 Jun;96(5):1069-84. doi: 10.1111/mmi.12991. Epub 2015 Apr 7.
Deinococcus radiodurans is known for its extreme radioresistance. Comparative genomics identified a radiation-desiccation response (RDR) regulon comprising genes that are highly induced after DNA damage and containing a conserved motif (RDRM) upstream of their coding region. We demonstrated that the
PMID 25754115

Japanese Journal

Functional characterization and substrate specificity of a novel gene encoding zinc finger-like protein, ZfLp, in Xenopus laevis oocytes

Kobayashi Yasuna,Umemoto Takahiro,Takeshita Yurie [他],KOHYAMA Noriko,OHBAYASHI Masayuki,SANADA Yutaka,YAMAMOTO Toshinori
Journal of toxicological sciences 37(4), 699-709, 2012-08-01
… The uptake of [3H]paclitaxel (taxol) by ZfLp was trans-stimulated by glutarate and glutathione (GSH). …
NAID 10030502147

Preparation of Hydrophilic Polymer Thin Films on Polytetrafluoroethylene by Plasma-Solution Interface Reaction

Yajima Tatsuhiko,Biligetu,Inamoto Masashi [他]
Journal of photopolymer science and technology 25(4), 511-517, 2012
NAID 40019347576

Clinical metabolomics using <SUP>1</SUP>H NMR spectral data in acute drug-induced liver injury

KIM Ji Won,JO Haeran,KIM Siwon,SEO Jeong Ju,CHA Jaemin,LEE Hae Won,LIM Mi-Sun,SEONG Sook Jin,KIM Suhkmann,YOON Young-Ran,KIM Kyu-Bong
日本毒性学会学術年会 39.2(0), AP-15, 2012
… In targeted profiling, urinary endogenous metabolites of trimethylamine-oxide, citrate, 3-chlorotyrosine, phenylalanine, glycine, alanine, taurine, betaine, glutarate, glutamine, and dimethylamine were significantly changed by APAP, while plasma metabolites of lactate, ethanol, isoleucine, choline, N-acetylglycine, and creatine were significantly changed. …
NAID 130005009086

「グルタル酸」

Glutaric acid
	IUPAC name pentanedioic acid
	Other names Propane-1,3-dicarboxylic acid; 1,3-propanedicarboxylic acid; pentanedioic acid; n-Pyrotartaric acid
Identifiers
CAS number	110-94-1
PubChem	743
ChemSpider	723
EC number	203-817-2
DrugBank	DB03553
KEGG	C00489
ChEBI	CHEBI:17859
ChEMBL	CHEMBL1162495
Jmol-3D images	Image 1
	SMILES C(CC(=O)O)CC(=O)O ;
	InChI InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9) ; Key: JFCQEDHGNNZCLN-UHFFFAOYSA-N InChI=1/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9); Key: JFCQEDHGNNZCLN-UHFFFAOYAU ;
Properties
Molecular formula	C5H8O4
Molar mass	132.12 g/mol
Melting point	95 to 98 °C
Boiling point	200 °C/20 mmHg
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: glutaric acid, glutarate
同: 1,3-プロパンジカルボン酸、n-ピロ酒石酸 n-pyrotartaric acid
関: glutaryl

name=グルタル酸
構造式=
IUPAC=1,5-ペンタン二酸
ペンタン-1,5-ジカルボン酸
別名=プロパン-1,3-ジカルボン酸
1,3-プロパンジカルボン酸
n-ピロ酒石酸
分子式=C₅H₈O₄
分子量=132.12
CAS登録番号=110-94-1
融点=95～98
沸点=200

グルタル酸(Glutaric acid)は示性式HOOC(CH₂)₃COOHで表されるカルボン酸の一つ。IUPAC命名法では1,5-ペンタン二酸(1,5-pentanedioic acid)またはペンタン-1,5-ジカルボン酸(pentane-1,5-dicarboxylic acid)である。無色からわずかに薄い黄色の結晶または結晶性粉末で、水に可溶、アルコール、エーテル (化学)に易溶。融点95～98℃、沸点302℃、分子量132.11。CAS登録番号は110-94-1。

グルタル酸は、トリプトファンの代謝経路であるグルタル酸経路や、代謝において最も重要なクエン酸回路に関与している。

2位にアミノ基が結合した2-アミノグルタル酸は、重要なアミノ酸であるグルタミン酸として知られる。

臨床関連

「α-ケトグルタル酸」

　　[★]

glutarate
英: α-ketoglutarate, α-ketoglutaric acid
同: 2-オキソグルタル酸 2-oxoglutaric acid 2-oxoglutarate
関: TCA回路

α-ケト酸α-keto acidの一つで、次のような糖質やアミノ酸の代謝中間体として重要。

代謝

生合成＠細胞質

細胞質内でイソクエン酸脱水素酵素とNADP＋により生成される。

クエン酸回路＠ミトコンドリア

オキサロ酢酸 ←(isocitrate dehydrogenase)→ α-ケトグルタル酸 + CO₂
α-ケトグルタル酸 + NAD⁺ + CoA-SH ←(α-ketoglutarate dehydrogenase complex)→ サクシニルCoA + NADH + H⁺ + CO₂

「glutaric acid」

　　[★]

グルタル酸

関: glutarate

「alpha-ketoglutarate dehydrogenase」

　　[★]

αケトグルタル酸脱水素酵素、αケトグルタル酸デヒドロゲナーゼ

関: ketoglutarate dehydrogenase complex

「ketoglutarate」

　　[★]

ケトグルタル酸、ケトグルタール酸

関: ketoglutaric acid

「oxoglutarate」

　　[★]

オキソグルタル酸

関: ketoglutaric acid

「2-oxoglutarate dehydrogenase」

　　[★] 2-オキソグルタル酸デヒドロゲナーゼ

[1] G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan (1963), "Glutaric Acid and Glutaramide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0496; Coll. Vol. 4: 496

[2] Peter Werle and Marcus Morawietz "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry: 2002, Wiley-VCH: Weinheim. DOI 10.1002/14356007.a01_305

リンク元	「グルタル酸」「α-ケトグルタル酸」「glutaric acid」
拡張検索	「alpha-ketoglutarate dehydrogenase」「ketoglutarate」「oxoglutarate」「2-oxoglutarate dehydrogenase」

匿名

検索

案内

案内

glutarate