ケト酸

関: keto acid

WordNet

acidosis with an accumulation of ketone bodies; occurs primarily in diabetes mellitus (同)diabetic_acidosis

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/15 14:01:31」(JST)

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Pyruvic acid (top), acetoacetic acid and levulinic acid (bottom)

Keto acids or ketoacids (also called oxo acids or oxoacids) are organic compounds that contain a carboxylic acid group and a ketone group.^[1] In several cases, the keto group is hydrated. The alpha-keto acids are especially important in biology as they are involved in the Krebs citric acid cycle and in glycolysis.^[2]

Common types of keto acids include:

Alpha-keto acids, or 2-oxoacids, such as pyruvic acid, have the keto group adjacent to the carboxylic acid. Another important member is oxaloacetic acid, a component of the Krebs cycle.^[3] Alpha-ketoglutarate, (also known as 2-oxo glutarate) is a 5-carbon keto acid derived from glutamic acid. Alpha-ketoglutarate participates in cell signaling by functioning as a cofactor for a variety of iron-containing redox enzymes, for example the proline hydroxylases that modify the hypoxia inducible factor leading to the destruction of HIF except in hypoxia when this pathway is blocked.^[4]
Beta-keto acids, or 3-oxoacids, such as acetoacetic acid, have the ketone group at the second carbon from the carboxylic acid. They can be formed by the Claisen condensation.
Gamma-keto acids, or 4-oxoacids, such as levulinic acid, have the ketone group at the third carbon from the carboxylic acid.

When ingested sugars and carbohydrate levels are low, stored fats and proteins are the primary source of energy production. Glucogenic amino acids from proteins are converted to glucose. Ketogenic amino acids can be deaminated to produce alpha keto acids and ketone bodies.

Alpha keto acids are used primarily as energy for liver cells and in fatty acid synthesis, also in the liver.

References

^ Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a18 313
^ Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
^ "α-Oxocarboxylic Acids" Robert C. Kerber, Marian S. Fernando J. Chem. Educ., 2010, doi:10.1021/ed1003096
^ The role of iron and 2-oxoglutarate oxygenases in signalling, Biochem Soc Trans. 2003 Jun;31(Pt 3):510-5

External links

Keto Acids at the US National Library of Medicine Medical Subject Headings (MeSH)

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1. 空腹時ケトアシドーシスおよびアルコール性ケトアシドーシス fasting ketosis and alcoholic ketoacidosis
2. 成人における糖尿病性ケトアシドーシスおよび高浸透圧性高血糖状態：疫学および病因 diabetic ketoacidosis and hyperosmolar hyperglycemic state in adults epidemiology and pathogenesis
3. 成人における糖尿病性ケトアシドーシスおよび高浸透圧性高血糖状態：臨床的特徴、評価、および診断 diabetic ketoacidosis and hyperosmolar hyperglycemic state in adults clinical features evaluation and diagnosis
4. 成人における代謝性アシドーシスへのアプローチ approach to the adult with metabolic acidosis
5. メープルシロップ尿症の概要 overview of maple syrup urine disease

English Journal

Asymmetric Stetter reactions catalyzed by thiamine diphosphate-dependent enzymes.

Kasparyan E1, Richter M, Dresen C, Walter LS, Fuchs G, Leeper FJ, Wacker T, Andrade SL, Kolter G, Pohl M, Müller M.
Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2014 Dec;98(23):9681-90. doi: 10.1007/s00253-014-5850-0. Epub 2014 Jun 24.
The intermolecular asymmetric Stetter reaction is an almost unexplored transformation for biocatalysts. Previously reported thiamine diphosphate (ThDP)-dependent PigD from Serratia marcescens is the first enzyme identified to catalyze the Stetter reaction of α,β-unsaturated ketones (Michael accept
PMID 24957249

Periocular photodynamic therapy for squamous intra-epidermal carcinoma.

Casie Chetty N1, Hemmant B, Skellett AM.
The Journal of dermatological treatment.J Dermatolog Treat.2014 Dec;25(6):516-8. doi: 10.3109/09546634.2013.849793. Epub 2013 Nov 12.
OBJECTIVES: To evaluate the response of Metvix photodynamic therapy (PDT) for the treatment of periocular Bowen's disease.METHODS: Four patients with biopsy-proven Bowen' disease were treated with Metvix PDT between November 2010 and January 2012. A detailed description of the technique used is desc
PMID 24215518

Topical photodynamic therapy of actinic keratoses with 5-aminolevulinic acid: randomized controlled trial with six months follow-up.

Buinauskaite E1, Maciulaitis R, Buinauskiene J, Valiukeviciene S.
The Journal of dermatological treatment.J Dermatolog Treat.2014 Dec;25(6):519-22. doi: 10.3109/09546634.2013.848257. Epub 2013 Nov 12.
BACKGROUND: Topical 5-aminolevulinic acid (ALA) photodynamic therapy (PDT) is an effective treatment for actinic keratosis (AK) with some transient adverse events.OBJECTIVE: The purpose of the study was to evaluate the efficacy and side effects of two different light doses when treating AKs with ALA
PMID 24215475

Japanese Journal

RpoS and oxidative stress conditions regulate succinyl-CoA : 3-ketoacid-coenzyme A transferase (SCOT) expression in Burkholderia pseudomallei

Chutoam Palatip,Charoensawan Varodom,Wongtrakoongate Patompon [他]
Microbiology and immunology 57(9), 605-615, 2013-09
NAID 40019798437

Molecular composition of dicarboxylic acids, ketocarboxylic acids, alpha-dicarbonyls and fatty acids in atmospheric aerosols from Tanzania, East Africa during wet and dry seasons

Mkoma S. L.,Kawamura K.
Atmospheric Chemistry and Physics 13(4), 2235-2251, 2013
… Oxalic acid (C-2) was found as the most abundant diacid species followed by succinic and/or malonic acids whereas glyoxylic acid and glyoxal were the dominant ketoacid and alpha-dicarbonyl, respectively in both seasons in PM2.5 and PM10. …
NAID 120005228647

分岐鎖アミノ酸代謝の調節機構:（平成23年度日本栄養・食糧学会学会賞受賞）

下村吉治
日本栄養・食糧学会誌 65(3), 97-103, 2012
分岐鎖アミノ酸（BCAA：ロイシン，イソロイシン，バリン）は，タンパク質の構成材料としてばかりでなく，タンパク質代謝および糖代謝を調節する生理作用の強い栄養因子であることが明らかにされつつある。よって，体内のBCAA 濃度の調節機構は種々の代謝を正常に保つために極めて重要である。体内には BCAA の分解系が存在するが，その分解系の調節がBCAA 濃度に影響を及ぼす。BCAA 分解系の律速は，その …
NAID 130002129282

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リンク元	「ケト酸」「keto acid」
拡張検索	「branched-chain α-ketoacid dehydrogenase deficiency」「diabetic ketoacidosis」「branched-chain α-ketoacid dehydrogenase」「ketoacidosis」

「ケト酸」

　　[★]

英: ketoacid, keto acid
同: ケトン酸、オキソ酸 oxoacid oxo acid
関: アミノ基転移

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ケトンのカルボニル基COとカルボキシル基のCOOHを含む有機化合物

ケトンとしての性質とカルボン酸としての性質を示す

アミノ基転移反応の際に、αケト酸はカルボニル基の炭素原子でアミノ酸からのアミノ基-NH₃を受け取る

ケト酸（ケトさん、Keto acid）は、ケトン基とカルボキシル基を含む有機酸である。

ケト酸のタイプには次のようなものがある。

α-ケト酸（2-オキソ酸）：ピルビン酸のようにケトン基がα炭素にあるもの。

ピルビン酸 CH₃COCOOH

β-ケト酸（3-オキソ酸）：アセト酢酸のようにケトン基がβ炭素にあるもの。

アセト酢酸 CH₃COCH₂COOH

γ-ケト酸（4-オキソ酸）：レブリン酸のようにケトン基がγ炭素にあるもの。

レブリン酸 CH₃COCH₂CH₂COOH

Pyruvic acid wiki structure.jpg

ピルビン酸
Acetoacetic acid wiki structure.jpg

アセト酢酸
Levulinic acid wiki structure.jpg

レブリン酸

「keto acid」

　　[★]

ケト酸

関: ketoacid

「branched-chain α-ketoacid dehydrogenase deficiency」

　　[★]

関: メープルシロップ尿症 maple syrup urine disease MSUD、分枝鎖αケト酸脱水素酵素

「diabetic ketoacidosis」

　　[★] 糖尿病性ケトアシドーシス DKA

「branched-chain α-ketoacid dehydrogenase」

　　[★] 分枝鎖αケト酸脱水素酵素

「ketoacidosis」

　　[★] ケトアシドーシス

[Ullmann-1] Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a18 313

[2] Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.

[3] "α-Oxocarboxylic Acids" Robert C. Kerber, Marian S. Fernando J. Chem. Educ., 2010, doi:10.1021/ed1003096

[4] The role of iron and 2-oxoglutarate oxygenases in signalling, Biochem Soc Trans. 2003 Jun;31(Pt 3):510-5

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ketoacid