Pyruvic acid
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| Pyruvic acid | |
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2-oxopropanoic acid |
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Other names
α-ketopropionic acid; acetylformic acid; pyroracemic acid; Pyr |
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| Identifiers | |
| CAS number | 127-17-3  |
| PubChem | 1060 |
| ChemSpider | 1031 |
| UNII | 8558G7RUTR |
| DrugBank | DB00119 |
| ChEBI | CHEBI:32816 |
| ChEMBL | CHEMBL1162144 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C3H4O3 |
| Molar mass | 88.06 g/mol |
| Density | 1.250 g/cm³ |
| Melting point |
11.8 °C, 285 K, 53 °F |
| Boiling point |
165 °C, 438 K, 329 °F |
| Acidity (pKa) | 2.50[1] |
| Related compounds | |
| Other anions | pyruvate ion  |
| Related keto-acids, carboxylic acids | acetic acid glyoxylic acid oxalic acid propionic acid acetoacetic acid |
| Related compounds | propionaldehyde glyceraldehyde methylglyoxal sodium pyruvate |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Pyruvic acid (CH3COCOOH) is an organic acid, a ketone, as well as 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.
Pyruvate 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.
Pyruvate 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 lactate when oxygen is lacking (fermentation).
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[edit] 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, 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
[edit] Biochemistry
Pyruvate is an important chemical compound in biochemistry. It is the output of the anaerobic metabolism of glucose known as glycolysis.[4] One molecule of glucose breaks down into two molecules of pyruvate[4], 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 called the citric 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 anaerobic respiration 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.
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.
[edit] Pyruvate 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 | |
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| ADP | ATP | ||
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| ADP | ATP | ||
| pyruvate kinase | |||
Compound C00074 at KEGG Pathway Database. Enzyme 2.7.1.40 at KEGG Pathway Database. Compound C00022 at KEGG Pathway Database.
[edit] Pyruvate decarboxylation to acetyl CoA
Pyruvate decarboxylation by the pyruvate dehydrogenase complex produces acetyl-CoA.
| pyruvate | pyruvate dehydrogenase complex | acetyl-CoA | |
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| CoA + NAD+ | CO2 + NADH + H+ | ||
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[edit] Pyruvate carboxylation to oxaloacetate
Carboxylation by the pyruvate carboxylase produces oxaloacetate.
| pyruvate | pyruvate carboxylase | oxaloacetate | |
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| ATP + CO2 | ADP + Pi | ||
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[edit] Transamination by the alanine aminotransferase
| pyruvate | alanine transaminase | alanine | |
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| glutamate | α-ketoglutarate | ||
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| glutamate | α-ketoglutarate | ||
[edit] Reduction to lactic acid
Reduction by the lactate dehydrogenase produces lactic acid.
| pyruvate | lactate dehydrogenase | lactic acid | |
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| NADH | NAD+ | ||
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| NADH | NAD+ | ||
[edit] Interactive pathway map
Click on genes, proteins and metabolites below to link to respective articles. [5]
[edit] See also
[edit] 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. http://books.google.com/books?id=Wq45AAAAcAAJ&pg=PA65&ved=0CEoQ6AEwBg#v=onepage&q&f=false. 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. http://books.google.com/books?id=MgA5AAAAIAAJ&pg=PA426&ved=0CE0Q6AEwCA#v=onepage&q&f=false. Retrieved December 1, 2010.
- ^ 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.
- ^ The interactive pathway map can be edited at WikiPathways: "TCA_Cycle_WP78". http://www.wikipathways.org/index.php/Pathway:WP78.
[edit] References
- Cody, G. D.; Boctor, N. Z.; Filley, T. R.; Hazen, R. M.; Scott, J. H.; Sharma, A.; Yoder, H. S.; Jr, (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.
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