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Pyruvic acid (CH₃COCOOH) is an organic acid, has a carboxylic acid and a ketone functional group, and is the simplest of the alpha-keto acids. The carboxylate (COO⁻) anion of pyruvic acid, its Brønsted–Lowry conjugate base, CH₃COCOO⁻, is known as pyruvate, and is a key intersection in several metabolic pathways.

Pyruvic acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through acetyl-CoA. It can also be used to construct the amino acid alanine and be converted into ethanol.

Pyruvic acid supplies energy to living cells through the citric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactic acid when oxygen is lacking (fermentation).

Chemistry

In 1834, Théophile-Jules Pelouze distilled both tartaric acid (L-tartaric acid) and racemic acid (a mix of D- and L-tartaric acid) and isolated pyrotartaric acid (methyl succinic acid^[2]) and another acid that Jöns Jacob Berzelius characterized the following year and named pyruvic acid.^[3] Pyruvic acid is a colorless liquid with a smell similar to that of acetic acid and is miscible with water. In the laboratory, pyruvic acid may be prepared by heating a mixture of tartaric acid and potassium hydrogen sulfate,^[4] by the oxidation of propylene glycol by a strong oxidizer (e.g., potassium permanganate or bleach), or by the hydrolysis of acetyl cyanide, formed by reaction of acetyl chloride with potassium cyanide:

CH₃COCl + KCN → CH₃COCN + KCl

CH₃COCN → CH₃COCOOH

Biochemistry

Pyruvate is an important chemical compound in biochemistry. It is the output of the anaerobic metabolism of glucose known as glycolysis.^[5] One molecule of glucose breaks down into two molecules of pyruvate,^[5] which are then used to provide further energy, in one of two ways. Pyruvate is converted into acetyl-coenzyme A, which is the main input for a series of reactions known as the Krebs cycle. Pyruvate is also converted to oxaloacetate by an anaplerotic reaction, which replenishes Krebs cycle intermediates; also, the oxaloacetate is used for gluconeogenesis. These reactions are named after Hans Adolf Krebs, the biochemist awarded the 1953 Nobel Prize for physiology, jointly with Fritz Lipmann, for research into metabolic processes. The cycle is also known as the citric acid cycle or tri-carboxylic acid cycle, because citric acid is one of the intermediate compounds formed during the reactions.

If insufficient oxygen is available, the acid is broken down anaerobically, creating lactate in animals and ethanol in plants and microorganisms. Pyruvate from glycolysis is converted by fermentation to lactate using the enzyme lactate dehydrogenase and the coenzyme NADH in lactate fermentation, or to acetaldehyde and then to ethanol in alcoholic fermentation.

Pyruvate is a key intersection in the network of metabolic pathways. Pyruvate can be converted into carbohydrates via gluconeogenesis, to fatty acids or energy through acetyl-CoA, to the amino acid alanine, and to ethanol. Therefore, it unites several key metabolic processes.

Reference ranges for blood tests, comparing blood content of pyruvate (shown in violet near middle) with other constituents.

Pyruvic acid production by glycolysis

In glycolysis, phosphoenolpyruvate (PEP) is converted to pyruvate by pyruvate kinase. This reaction is strongly exergonic and irreversible; in gluconeogenesis, it takes two enzymes, pyruvate carboxylase and PEP carboxykinase, to catalyze the reverse transformation of pyruvate to PEP.

phosphoenolpyruvate	pyruvate kinase		pyruvate

	ADP	ATP

	ADP	ATP

	pyruvate carboxylase and PEP carboxykinase

Compound C00074 at KEGG Pathway Database. Enzyme 2.7.1.40 at KEGG Pathway Database. Compound C00022 at KEGG Pathway Database.

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

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Glycolysis and Gluconeogenesis edit

^ The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

Decarboxylation to acetyl CoA

Pyruvate decarboxylation by the pyruvate dehydrogenase complex produces acetyl-CoA.

pyruvate	pyruvate dehydrogenase complex		acetyl-CoA

	CoA + NAD⁺	CO₂ + NADH + H⁺

Carboxylation to oxaloacetate

Carboxylation by pyruvate carboxylase produces oxaloacetate.

pyruvate	pyruvate carboxylase		oxaloacetate

	ATP + CO₂	ADP + P_i

Transamination to alanine

Transamination by alanine transaminase produces alanine.

pyruvate	alanine transaminase		alanine

	glutamate	α-ketoglutarate

	glutamate	α-ketoglutarate

Reduction to lactate

Reduction by lactate dehydrogenase produces lactate.

pyruvate	lactate dehydrogenase		lactate

	NADH	NAD⁺

	NADH	NAD⁺

Uses

The pyruvic acid derivative bromopyruvic acid is being studied for potential cancer treatment applications by researchers at Johns Hopkins University in ways that would support the Warburg hypothesis on the cause(s) of cancer.^{[citation needed]}

Pyruvate is sold as a weight-loss supplement, though evidence supporting this use is lacking. A systematic review of six trials found a statistically significant difference in body weight with pyruvate compared to placebo. However, all of the trials had methodological weaknesses and the magnitude of the effect was small. The review also identified adverse events associated with pyruvate such as diarrhea, bloating, gas, and increase in low-density lipoprotein (LDL) cholesterol. The authors concluded that there was insufficient evidence to support the use of pyruvate for weight loss.^[6]

Notes

^ Dawson, R. M. C. et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
^ Thomson, Thomas (1838). "II. Of fixed acids Section". Chemistry of organic bodies, vegetables. London: J. B. Baillière. p. 65. Retrieved December 1, 2010.
^ Thorpe, Sir Thomas Edward (1922). "Glutaric acid". A dictionary of applied chemistry 3. London: Longmans, Green, and Co. pp. 426–427. Retrieved December 1, 2010.
^ Organic Syntheses, Coll. Vol. 1, p.475 (1941); Vol. 4, p.63 (1925)
^ ^a ^b Lehninger, Albert L.; Nelson, David L.; Cox, Michael M. (2008). Principles of Biochemistry (5th ed.). New York, NY: W.H. Freeman and Company. p. 528. ISBN 978-0-7167-7108-1.
^ Onakpoya I, Hunt K, Wider B, Ernst E. "Pyruvate supplementation for weight loss: a systematic review and meta-analysis of randomized clinical trials.". Critical Reviews in Food Science and Nutrition. Retrieved 26 November 2013.

References

Cody, G. D.; Boctor, N. Z.; Filley, T. R.; Hazen, R. M.; Scott, J. H.; Sharma, A.; Yoder Jr, H. S. (2000). "Primordial Carbonylated Iron-Sulfur Compounds and the Synthesis of Pyruvate". Science 289 (5483): 1337–1340. Bibcode:2000Sci...289.1337C. doi:10.1126/science.289.5483.1337. PMID 10958777. edit

External links

Pyruvic acid MS Spectrum

Wikimedia Commons has media related to Pyruvic acid.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. ピルビン酸キナーゼ欠損症 pyruvate kinase deficiency
2. 先天性代謝異常：個々の障害の発見 inborn errors of metabolism identifying the specific disorder
3. ミトコンドリアミオパシー：臨床的特徴および診断 mitochondrial myopathies clinical features and diagnosis
4. 幼児および小児における低血糖症の病因 etiology of hypoglycemia in infants and children
5. 乳酸アシドーシスの原因 causes of lactic acidosis

Japanese Journal

〈Original Papers〉Tanticharoenia sakaeratensisの高濃度グルコース耐性代謝に関するプロテオーム解析

波多野裕美,武部聡,東慶直
Memoirs of the Faculty of Biology-Oriented Science and Technology of Kinki University (28), 95-107, 2011-9
… Comparison of protein profiles and amino acid sequencing indicates that accumulation of several geneproducts were regulated by the glucose concentration, e.g. one gene product involved in a pyruvate metabolism was accumulated and outer membrane proteins were decreased in the 30％ glucose condition. …
NAID 120003460252

吟醸酒製造用清酒酵母からのピルビン酸低生産株の育種と実製造でのピルビン酸およびα-アセト乳酸の低減

佐々木真,大場孝宏,末永光,稲橋正明,佐藤真佐恵,鶴田裕美,小林元太,柘植圭介,吉村臣史,小金丸和義,北垣浩志
生物工学会誌 : seibutsu-kogaku kaishi 89(5), 222-227, 2011-05-25
… Since residual pyruvate during sake brewing leads to generation of off-flavours such as acetaldehyde and diacetyl, many researchers have challenged to develop a method to decrease pyruvate level during sake brewing. … Particularly, during brewing of ginjo sake, the decrease of pyruvate level tends to be slow and a technology to decrease pyruvate level will be beneficial to improve the quality of flavour and taste of ginjo sake. …
NAID 110008662241

Related Pictures

★リンクテーブル★

リンク元	「解糖系」「ピルビン酸」「ビオチン」「ピルビン酸塩」「pyruvic acid」
拡張検索	「pyruvate orthophosphate dikinase」「phosphoenolpyruvate kinase」「beta-alanine-pyruvate transaminase」「pyruvate carboxylase deficiency disease」「inborn error of pyruvate metabolism」

「解糖系」

Pyruvic acid
	IUPAC name 2-oxopropanoic acid
	Other names α-ketopropionic acid; acetylformic acid; pyroracemic acid; Pyr
Identifiers
CAS number	127-17-3
PubChem	1060
ChemSpider	1031
UNII	8558G7RUTR
DrugBank	DB00119
KEGG	C00022
ChEBI	CHEBI:32816
ChEMBL	CHEMBL1162144
Jmol-3D images	Image 1
	SMILES O=C(C(=O)O)C ;
	InChI InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6) ; Key: LCTONWCANYUPML-UHFFFAOYSA-N ;
Properties
Molecular formula	C3H4O3
Molar mass	88.06 g/mol
Density	1.250 g/cm³
Melting point	11.8 °C (53.2 °F; 284.9 K)
Boiling point	165 °C (329 °F; 438 K)
Acidity (pKa)	2.50
Related compounds
Other anions	pyruvate ion; ion of pyruvic acid
Related keto-acids, carboxylic acids	acetic acid; glyoxylic acid; oxalic acid; propionic acid; acetoacetic acid
Related compounds	propionaldehyde; glyceraldehyde; methylglyoxal; sodium pyruvate
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	(verify) (what is: /?)
	Infobox references

　　[★]

英: glycolytic pathway
同: エムデン-マイヤーホフ経路 Embden-Meyerhof pathway
関: 解糖、TCA回路

CH(OH)-CH(OH)-C(OH)H-CH(OH)-C(CH2OH)H-O- グルコース (OHが↓↓↑↓↑)
CH(OH)-CH(OH)-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- グルコース-6-リン酸 (OHが↓↓↑↓↑)
C(CH2OH)OH-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- フルクトース-6-リン酸
C(CH2O-PO3)OH-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- フルクトース-1,6-リン酸

glucose
↓-hexokinase/glucokinase(liver)
glucose 6-phosphate
↓-phosphohexose isomerase
fructose 6-phosphate
↓-phosphofructokinase
fructose 1,6-bisphosphate
↓-aldolase
glyceraldehyde 3-phosphate
↓-glyceraldehyde-3-phosphate dehydrogenase
1,3-bisphosphoglycerate
↓-phosphoglycerate kinase →ATP
3-phosphoglycerate
↓-phosphoglyceate mutase
2-phosphoglycerate
↓-enolase
phosphoenolpyruvate
↓-pyruvate kinase → ATP
pyruvate
　－(pyruvate dehydrogenase)→acetyl-CoA
　－(pyruvate carboxylase)→oxaloacetate－(NADH+H+)→malate

解糖系の酵素 (first aid step1 2006 p.87, FASTEP1_87_酵素一覧.xls)

1	galactokinase	キナーゼ
2	galactose-1-phosphate uridyltransferase	転移酵素
3	hexokinase/glucokinase	キナーゼ
4	glucose-6-phosphatase	ホスファターゼ
5	glucose-6-phosphate dehydrogenase	脱水素酵素
6	transketolase
7	phosphofructokinase	キナーゼ
8	fructose-1,6-bisphosphatase	ホスファターゼ
9	fructokinase	キナーゼ	フルクトキナーゼ
10	aldolase B		アルドラーゼ
11	pyruvate kinase	キナーゼ	ピルビン酸キナーゼ
12	pyruvate dehydrogenase	脱水素酵素	ピルビン酸デヒドロゲナーゼ
13	HMG-CoA reductase	還元酵素	HMG-CoA還元酵素
14	pyruvate carboxylase	カルボキシラーゼ	ピルビン酸カルボキシラーゼ
15	PEP carboxykinase	キナーゼ	PEPカルボキシキナーゼ
16	citrate synthase	合成酵素	クエン酸合成酵素
17	α-ketoglutarate dehydrogenase	脱水素酵素	α-ケトグルタミン酸脱水素酵素
18	ornithine transcarbamylase	転移酵素	オルニチンカルバモイルトランスフェラーゼ

「ピルビン酸」

　　[★]

英: pyruvate, pyruvic acid, 2-oxopropanic acid, α-ketopropionic acid
同: 焦性ブドウ酸 pyroracemic acid
関: 解糖系

α-ケト酸である。

CH₃-CO-COOH

CoAとピルビン酸デヒドロゲナーゼにより、脱炭酸し、アセチルCoA(CH₃-CO-CoA)となる。

ピルビン酸の生合成反応

ピルビン酸合成 (ホスホエノールピルビン酸 + ADP　→ ピルビン酸 + ATP)

CH₂-C(OPO₃^2-)-COOH + ADP + H⁺ －(ピルビン酸キナーゼ)→  CH₃-CO-COO^- + ATP

反応

1. 乳酸合成　：乳酸デヒドロゲナーゼ：可逆：細胞質：筋肉、赤血球の不要物(ピルビン酸)→肝臓へ転送
2. アセチルCoA合成　：ピルビン酸デヒドロゲナーゼ：ミトコンドリア：不可逆：TCA回路の基質
3. オキサロ酢酸合成　：ピルビン酸カルボキシラーゼ：ミトコンドリア：可逆：TCA回路の基質、糖新生

　　CH₃-CO-COO^- + ATP + CO₂　－→　HOOC-CO-CH₂-COOH + Pi

4. アラニン合成　：アラニンアミノトランスフェラーゼ：細胞質：可逆：アミノ基のキャリア。筋肉の不要物(アミノ基)→肝臓

5. アセトアルデヒド産生

ピルビン酸－(ピルビン酸デカルボキシラーゼ)→アセトアルデヒド + CO₂

「ビオチン」

　　[★]

英: biotin
同: ビタミンB₇ vitamin B₇、補酵素R coenzyme R、ビタミンH vitamin H
関: ビタミン

機能

カルボキシラーゼの補酵素となり、CO₂キャリアーとして機能
体内で代謝されてビオチン酵素となり、炭素固定反応の補酵素となる。

1. pyruvate －(ピルビン酸カルボキシラーゼ)→ oxaloacetate

2. acetyl-CoA －(アセチルCoAカルボキシラーゼ)→ malonyl-CoA

3. proprionyl-CoA －(プロピオニルCoAカルボキシラーゼ)→ methylmalonyl-CoA　：奇数炭素脂肪酸の偶数炭素脂肪酸への変換、2-オキソ酪酸の代謝

臨床関連

ビオチン欠乏

dermatitis, enteritis. Caused by antibiotic use, ingestion of raw eggs. (FIRST AID step1 p.114)
アビジンと強固に結合する。卵白の過剰摂取によりビオチンの吸収が妨げられ欠乏症を生じうる。

「ピルビン酸塩」

　　[★]

英: pyruvate
関: ピルビン酸

「pyruvic acid」

　　[★] ピルビン酸 pyruvate

「pyruvate orthophosphate dikinase」

　　[★]

ピルビン酸リン酸ジキナーゼ、ピルビン酸正リン酸ジキナーゼ

「phosphoenolpyruvate kinase」

　　[★] ピルビン酸キナーゼ。ホスホエノールピルビン酸キナーゼ

「beta-alanine-pyruvate transaminase」

　　[★]

βアラニンピルビン酸トランスアミナーゼ

「pyruvate carboxylase deficiency disease」

　　[★]

ピルビン酸カルボキシラーゼ欠損症

「inborn error of pyruvate metabolism」

　　[★]

先天性ピルビン酸代謝異常

[WikiPathways-6] The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

[1] Dawson, R. M. C. et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.

[2] Thomson, Thomas (1838). "II. Of fixed acids Section". Chemistry of organic bodies, vegetables. London: J. B. Baillière. p. 65. Retrieved December 1, 2010.

[3] Thorpe, Sir Thomas Edward (1922). "Glutaric acid". A dictionary of applied chemistry 3. London: Longmans, Green, and Co. pp. 426–427. Retrieved December 1, 2010.

[4] Organic Syntheses, Coll. Vol. 1, p.475 (1941); Vol. 4, p.63 (1925)

[lehninger528-5] Lehninger, Albert L.; Nelson, David L.; Cox, Michael M. (2008). Principles of Biochemistry (5th ed.). New York, NY: W.H. Freeman and Company. p. 528. ISBN 978-0-7167-7108-1.

[7] Onakpoya I, Hunt K, Wider B, Ernst E. "Pyruvate supplementation for weight loss: a systematic review and meta-analysis of randomized clinical trials.". Critical Reviews in Food Science and Nutrition. Retrieved 26 November 2013.

匿名

検索

案内

pyruvate