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Pyruvic acid

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Pyruvic acid
Pyruvic-acid-2D-skeletal Pyruvic-acid-3D-balls
Chemical name 2-oxopropanoic acid
Other names α-ketopropionic acid
acetylformic acid
pyroracemic acid
Pyr
Chemical formula C3H4O3
Molecular mass 88.06 g/mol
CAS number [127-17-3]
Density 1.250 g/cm³
Melting point 11.8 °C
Boiling point 165 °C
SMILES CC(C(O)=O)=O
Disclaimer and references

Pyruvic acid (CH3COCO2H) is an alpha-keto acid which plays an important role in biochemical processes. The carboxylate anion of pyruvic acid is known as pyruvate.

ChemistryEdit

Pyruvic acid is a colorless liquid with a smell similar to acetic acid. It is miscible with water, and soluble in ethanol and diethyl ether. In the laboratory, pyruvic acid may be prepared by heating a mixture of tartaric acid and potassium hydrogen sulfate, or by the hydrolysis of acetyl cyanide, formed by reaction of acetyl chloride with potassium cyanide:

CH3COCl + KCN → CH3COCN
CH3COCN → CH3COCOOH

Biochemical roleEdit

Pyruvate is an important chemical compound in biochemistry. It is the output of the metabolism of glucose known as glycolysis. One molecule of glucose breaks down into two molecules of pyruvic acid, which are then used to provide further energy, in one of two ways. Provided that sufficient oxygen is available, pyruvic acid 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 and then further broken down to carbon dioxide. 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 lactic acid in animals and ethanol in plants. 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.

Pyruvic acid is a key intersection in the network of metabolic pathways. Pyruvic acid can be converted to 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.

3-bromopyruvate has been studied for potential cancer treatment applications, by Young Hee Ko, Ph.D., at Johns Hopkins University [[1]].

Pyruvate production by glycolysisEdit

Template:Enzymatic Reaction Compound C00074 at KEGG Pathway Database.

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


This reaction is not reversible and cannot proceed in the direction of PEP.

Pyruvate decarboxylation to acetyl CoAEdit

Template:Enzymatic ReactionNote that decarboxylation is only one of several possible reactions for pyruvate.

Pyruvic acid's role in the origin of lifeEdit

Main article: iron-sulfur world theory

Current evolutionary theory on the origin of life posits that the first organisms were anaerobic because the atmosphere of prebiotic Earth was almost devoid of oxygen. As such, requisite biochemical materials must have preceded life and recent experiments indicate that pyruvate can be synthesized abiotically. In vitro, iron sulfide at sufficient pressure and temperature catalyzes the formation of pyruvic acid. Thus, argues Günter Wächtershäuser, the mixing of iron-rich crust with hydrothermal vent fluid is suspected of providing the fertile basis for the formation of life.

See alsoEdit



References Edit

  • George D. Cody, Nabil Z. Boctor, Timothy R. Filley, Robert M. Hazen, James H. Scott, Anurag Sharma, Hatten S. Yoder Jr., "Primordial Carbonylated Iron-Sulfur Compounds and the Synthesis of Pyruvate," Science, 289 (5483) (25 August 2000) pp. 1337 - 1340. [2]

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