オキサロ酢酸

オキサロ酢酸
識別情報
CAS登録番号 328-42-7
EC番号 206-329-8
KEGG C00036
特性
化学式 C4H4O5
モル質量 132.07g/mol
示性式 CH2CO(COOH)2
密度 ? g/cm3
融点

161℃

熱化学
標準生成熱 ΔfHo -943.21 kJ/mol
標準燃焼熱 ΔcHo -1205.58 kJ/mol
特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

オキサロ酢酸(オキサロさくさん、Oxaloacetic acid)は、ジカルボン酸の一種。IUPAC命名法では2-オキソブタン二酸 (2-oxobutanedioic acid) になる。旧名オキサル酢酸。

生化学

クエン酸回路

オキサロ酢酸は、クエン酸回路およびグリオキシル酸回路を構成する物質のひとつで、リンゴ酸リンゴ酸デヒドロゲナーゼによって酸化されて生成する。オキサロ酢酸は、クエン酸シンターゼによってアセチルCoAと反応してクエン酸となる。

糖新生

オキサロ酢酸は、ホスホエノールピルビン酸を経由して糖新生にも利用される[1][信頼性要検証]ピルビン酸は最初にミトコンドリアピルビン酸カルボキシラーゼによってオキサロ酢酸に変換される。その間ATPが1分子加水分解される。そのときオキサロ酢酸は、ホスホエノールピルビン酸カルボキシキナーゼによって脱炭酸リン酸化反応が同時に触媒され、細胞質にホスホエノールピルビン酸が生成する。ホスホエノールピルビン酸は、オキサロ酢酸の脱炭酸によって生じ、1分子のGTP加水分解し、この反応はホスホエノールピルビン酸カルボキシキナーゼによって触媒され、糖新生の律速段階となる[2]。 オキサロ酢酸はそのままではミトコンドリアの内膜を通過できないので、ミトコンドリアから細胞質へのホスホエノールピルビン酸の輸送は、リンゴ酸/ホスホエノールピルビン酸シャトルによって調停される。

リンゴ酸-アスパラギン酸シャトル

アスパラギン酸(aspartic acid)、リンゴ酸(malic acid)との関係

リンゴ酸-アスパラギン酸シャトルにおいて、アスパラギン酸アミノトランスフェラーゼによってグルタミン酸と反応することによってα-ケトグルタル酸アスパラギン酸となる。

その他の生化学反応

オキサロ酢酸は、常温では不安定で、脱炭酸化が起きてピルビン酸となる。

抗老化

線虫にオキサロ酢酸を摂取させると2mMolでは効果がなかったが8mMolで平均25%ほど寿命が伸びることがわかった。[3]

関連項目

出典

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