Pyruvic acid

Chembox new
Name = Pyruvic acid
ImageFileL1 = Pyruvic-acid-2D-skeletal.png ImageSizeL1 = 120px
ImageFileR1 = Pyruvic-acid-3D-balls.png ImageSizeR1 = 120px
IUPACName = 2-oxopropanoic acid
OtherNames = α-ketopropionic acid; acetylformic acid; pyroracemic acid; Pyr
Section1 = Chembox Identifiers
CASNo = 127-17-3
ChemSpiderID = 1031
SMILES = CC(C(O)=O)=O
Section2 = Chembox Properties
Formula = C₃H₄O₃
MolarMass = 88.06 g/mol
Density = 1.250 g/cm³
MeltingPt = 11.8 °C
BoilingPt = 165 °C

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

Chemistry

Pyruvic acid is a colorless liquid with a smell similar to that of 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, by the oxidation of propylene glycol by a strong oxidizer (eg. potassium permanganate or bleach), or by the hydrolysis of acetyl cyanide, formed by reaction of acetyl chloride with potassium cyanide:

:CH₃COCl + KCN → CH₃COCN:CH₃COCN → CH₃COCOOH

Biochemistry

Pyruvate is an important chemical compound in biochemistry. It is the output of the anaerobic metabolism of glucose known as glycolysis. One molecule of glucose breaks down into two molecules of pyruvate, 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; alternatively, 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. 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 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 researchers at Johns Hopkins University in ways that would support the Warburg hypothesis on the cause(s) of cancer.

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.Enzymatic Reaction
foward_enzyme=Pyruvate kinase
reverse_enzyme=Pyruvate kinase
substrate=phosphoenolpyruvate
product=pyruvate
reaction_direction_(foward/reversible/reverse)=reversible
minor_foward_substrate(s)=ADP
minor_foward_product(s)=ATP
minor_reverse_substrate(s)=ATP
minor_reverse_product(s)=ADP
substrate_

product_

Pyruvate decarboxylation to acetyl CoA

Pyruvate decarboxylation by the pyruvate dehydrogenase complex produces acetyl-CoA.Enzymatic Reaction
foward_enzyme=pyruvate dehydrogenase complex
reverse_enzyme=
substrate=pyruvate
product=acetyl-CoA
reaction_direction_(foward/reversible/reverse)=foward
minor_foward_substrate(s)= CoA + NAD⁺
minor_foward_product(s)= CO₂ + NADH + H⁺
minor_reverse_substrate(s)=
minor_reverse_product(s)=
substrate_

product_

Pyruvate carboxylation to oxaloacetate

Carboxylation by the pyruvate carboxylase produces oxaloacetate.Enzymatic Reaction
foward_enzyme=pyruvate carboxylase
reverse_enzyme=
substrate=pyruvate
product=oxaloacetate
reaction_direction_(foward/reversible/reverse)=foward
minor_foward_substrate(s)= ATP + CO₂
minor_foward_product(s)= ADP + P_i
minor_reverse_substrate(s)=
minor_reverse_product(s)=
substrate_

product_

Transamination by the alanine aminotransferase

Enzymatic Reaction
foward_enzyme=Alanine transaminase
reverse_enzyme=
substrate=pyruvate
product=alanine
reaction_direction_(foward/reversible/reverse)=reversible
minor_foward_substrate(s)= Glutamate
minor_foward_product(s)= α-ketoglutarate
minor_reverse_substrate(s)= α-ketoglutarate
minor_reverse_product(s)= Glutamate
substrate_

product_

Reduction to lactate

Reduction by the lactate dehydrogenase produces lactate.Enzymatic Reaction
foward_enzyme=lactate dehydrogenase
reverse_enzyme=
substrate=pyruvate
product=lactate
reaction_direction_(foward/reversible/reverse)=reversible
minor_foward_substrate(s)= NADH
minor_foward_product(s)= NAD⁺
minor_reverse_substrate(s)= NAD⁺
minor_reverse_product(s)= NADH
substrate_

product_

---

Origin of life

Current evolutionary theory on the origin of life posits that the first organisms were anaerobic because the atmosphere of prebiotic Earth was, in theory, almost devoid of oxygen. As such, requisite biochemical materials must have preceded life. In vitro, iron sulfide at sufficient pressure and temperature catalyzes the formation of pyruvate. 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.

References

* 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. [http://www.sciencemag.org/cgi/content/abstract/sci;289/5483/1337]

External links

* [http://www.emphycorp.com/cancerprevention.html "Pyruvate in Cancer Prevention and Treatment"]
* [http://www.hopkinsmedicine.org/Press_releases/2004/10_14_04.html "ENERGY BLOCKER" KILLS BIG TUMORS IN RATS] , research at Johns Hopkins on pyruvate
* [http://www.merriam-webster.com/dictionary/pyruvic%20acid "Latin uva grapes"]