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Information about Pyruvate

Pyruvic acid
IUPAC name2-oxopropanoic acid
Other namesα-ketopropionic acid; acetylformic acid; pyroracemic acid; Pyr
Identifiers
CAS number127-17-3
SMILESCC(C(O)=O)=O
Properties
Molecular formulaC3H4O3
Molar mass88.06 g/mol
Density1.250 g/cm³
Melting point 11.8 °C
Boiling point 165 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 C, 100 kPa)
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.

Chemistry

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 role

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.

The pyruvic acid derivative bromopyruvic acid is being studied for potential cancer treatment applications, by Young Hee Ko at Johns Hopkins University and others in ways that would support the Warburg hypothesis on the cause(s) of cancer.

Pyruvate production by glycolysis

phosphoenolpyruvatePyruvate kinasepyruvate
 
ADPATP
ADPATP
 
 Pyruvate kinase
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 CoA

pyruvatepyruvate dehydrogenase complexacetyl CoA
 
CoA + NAD+CO2 + NADH + H+
 
 
Note that decarboxylation is only one of several possible reactions for pyruvate.

Pyruvic acid's role in the origin of life

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 also


References

External links

IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
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In physics, density is mass m per unit volume V—how heavy something is compared to its size. A small, heavy object, such as a rock or a lump of lead, is denser than a lighter object of the same size or a larger object of the same weight, such as pieces of
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The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. Although the phrase would suggest a specific temperature and is commonly and incorrectly used as such in most textbooks and literature, most crystalline compounds
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boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.[1][2][3][4]
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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Keto acids are organic acids containing a ketone functional group and a carboxylic acid group.

Common types of keto acids include:
  • Alpha-keto acids, or 2-oxo acids, such as pyruvic acid have the keto group adjacent to the carboxylic acid

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Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted acids — they are proton donors.
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Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. Its structural formula is represented as CH3COOH.
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Miscibility is a term in chemistry that refers to the property of liquids to mix in all proportions, forming a homogeneous solution. In principle, the term applies also to other phases (solids and gases), but the main focus on the solubility of one liquid in another.
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Ethanol, also known as ethyl alcohol, drinking alcohol or grain alcohol, is a flammable, colorless, slightly toxic chemical compound, and is best known as the alcohol found in alcoholic beverages.
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Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic smell. It is the most common member of a class of chemical compounds known generically as ethers.
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Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes, bananas, and tamarinds, and is one of the main acids found in wine. It is added to other foods to give a sour taste, and is used as an antioxidant.

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This chemistry related article lacks information on the notability (importance) of the subject matter.
Please help [ improve this article] by providing context for a general audience, especially in the lead section. This article has been tagged since July 2006.
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Acetyl chloride, also known as ethanoyl chloride, is an acid chloride (also known as an acyl chloride) derived from acetic acid (ethanoic acid). It has the formula CH3COCl and it belongs to the class of organic compounds called acyl halides.
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Potassium cyanide or KCN is the potassium salt of hydrogen cyanide or hydrocyanic acid. It is a colorless crystalline compound, similar in appearance to sugar, and highly soluble in water.
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Biochemistry is the study of the chemical processes in living organisms.[1] The word "biochemistry" comes from the Greek word βιοχημεία biochēmeia, which means "the chemistry of life.
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Glucose (Glc), a monosaccharide (or simple sugar), is an important carbohydrate in biology. The living cell uses it as a source of energy and metabolic intermediate.
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Embden-Meyerhof pathway, initially explained by Gustav Embden and Otto Meyerhof. The term can be taken to include alternative pathways, such as the Entner-Doudoroff Pathway. However, glycolysis will be used here as a synonym for the Embden-Meyerhof pathway.
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Glucose (Glc), a monosaccharide (or simple sugar), is an important carbohydrate in biology. The living cell uses it as a source of energy and metabolic intermediate.
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2, −1
(neutral oxide)
Electronegativity 3.44 (Pauling scale)
Ionization energies
(more) 1st: 1313.9 kJmol−1
2nd: 3388.3 kJmol−1
3rd: 5300.5 kJmol−1

Atomic radius 60 pm
Atomic radius (calc.
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Acetyl-CoA is an important molecule in metabolism, used in many biochemical reactions. Its main use is to convey the carbon atoms within the acetyl group to Krebs Cycle to be oxidized for energy production.
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citric acid cycle, also known as the tricarboxylic acid (TCA) cycle, the Krebs cycle, or Szent-Györgyi-Krebs cycle (after Hans Adolf Krebs and Albert Szent-Györgyi who first determined the chemical intermediates and reaction sequence of the cycle), is a series
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Oxaloacetic acid is an organic compound with the chemical formula HO2CC(O)CH2CO2H. It also has other names (see Table) and its conjugate base is called "oxaloacetate.
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Anaplerotic reactions are those that form intermediates of the TCA or citric acid cycle. The malate is created by PEP carboxylase and malate dehydrogenase in the cytosol. Malate, in the mitochondrial matrix, can be used to make pyruvate (catalyzed by NAD+ malic enzyme) or
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Carbon dioxide is a chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state.
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