Pyruvic acid

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Pyruvic acid
Pyruvic-acid-2D-skeletal.jpg
Pyruvic-acid-3D-balls.jpg
IUPAC name 2-oxopropanoic acid
Other names α-ketopropionic acid; acetylformic acid; pyroracemic acid; Pyr
Identifiers
CAS number 127-17-3
SMILES CC(C(O)=O)=O
Properties
Molecular formula C3H4O3
Molar mass 88.06 g/mol
Density 1.250 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)

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Overview

Pyruvic acid (CH3COCO2H) is an alpha-keto acid. Pyruvate 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 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, 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 aerobic 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. 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 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 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

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. The arrow indicating a reverse reaction in the Figure below is incorrect.

phosphoenolpyruvate Pyruvate kinase pyruvate
Phosphoenolpyruvate wpmp.png   Pyruvate wpmp.png
ADP ATP
Biochem reaction arrow reversible YYYY horiz med.png
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.

Pyruvate decarboxylation to acetyl CoA

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

pyruvate pyruvate dehydrogenase complex acetyl-CoA
Pyruvate wpmp.png   Acetyl co-A wpmp.png
CoA + NAD+ CO2 + NADH + H+
Biochem reaction arrow foward YYNN horiz med.png
 
 

Note that decarboxylation is only one of several possible reactions for pyruvate.

Role in the 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 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.

External links

 v  d  e 
Glycolysis Metabolic Pathway
Glucose Hexokinase Glucose-6-phosphate Phosphoglucoisomerase Fructose 6-phosphate Phosphofructokinase Fructose 1,6-bisphosphate Fructose bisphosphate aldolase Dihydroxyacetone phosphate Glyceraldehyde 3-phosphate Triosephosphate isomerase Glyceraldehyde 3-phosphate Glyceraldehyde phosphate dehydrogenase
D-glucose wpmp.png ATP ADP Alpha-D-glucose-6-phosphate wpmp.png Beta-D-fructose-6-phosphate wpmp.png ATP ADP Beta-D-fructose-1,6-bisphosphate wpmp.png Glycerone-phosphate wpmp.png D-glyceraldehyde-3-phosphate wpmp.png D-glyceraldehyde-3-phosphate wpmp.png NAD+ + Pi NADH + H+
Biochem reaction arrow foward YYNN horiz med.png Biochem reaction arrow reversible NNNN horiz med.png Biochem reaction arrow foward YYNN horiz med.png Biochem reaction arrow reversible NNNN horiz med.png + Biochem reaction arrow reversible NNNN horiz med.png 2 Biochem reaction arrow reversible YYYY horiz med.png
NAD+ + Pi NADH + H+
1,3-Bisphosphoglycerate Phosphoglycerate kinase 3-Phosphoglycerate Phosphoglycerate mutase 2-Phosphoglycerate Enolase Phosphoenolpyruvate Pyruvate kinase Pyruvate Pyruvate dehydrogenase Acetyl-CoA
1,3-bisphospho-D-glycerate wpmp.png ADP ATP 3-phospho-D-glycerate wpmp.png 2-phospho-D-glycerate wpmp.png H2O Phosphoenolpyruvate wpmp.png ADP ATP Pyruvate wpmp.png CoA + NAD+ NADH + H+ + CO2 Acetyl co-A wpmp.png
2 Biochem reaction arrow reversible YYYY horiz med.png 2 Biochem reaction arrow reversible NNNN horiz med.png 2 Biochem reaction arrow reversible NYYN horiz med.png 2 Biochem reaction arrow foward YYNN horiz med.png 2 Biochem reaction arrow foward YYNN horiz med.png 2
ADP ATP H2O

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. [2]
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| group5 = Clinical Trials Involving Pyruvic acid | list5 = Ongoing Trials on Pyruvic acid at Clinical Trials.govTrial results on Pyruvic acidClinical Trials on Pyruvic acid at Google


| group6 = Guidelines / Policies / Government Resources (FDA/CDC) Regarding Pyruvic acid | list6 = US National Guidelines Clearinghouse on Pyruvic acidNICE Guidance on Pyruvic acidNHS PRODIGY GuidanceFDA on Pyruvic acidCDC on Pyruvic acid


| group7 = Textbook Information on Pyruvic acid | list7 = Books and Textbook Information on Pyruvic acid


| group8 = Pharmacology Resources on Pyruvic acid | list8 = AND (Dose)}} Dosing of Pyruvic acidAND (drug interactions)}} Drug interactions with Pyruvic acidAND (side effects)}} Side effects of Pyruvic acidAND (Allergy)}} Allergic reactions to Pyruvic acidAND (overdose)}} Overdose information on Pyruvic acidAND (carcinogenicity)}} Carcinogenicity information on Pyruvic acidAND (pregnancy)}} Pyruvic acid in pregnancyAND (pharmacokinetics)}} Pharmacokinetics of Pyruvic acid


| group9 = Genetics, Pharmacogenomics, and Proteinomics of Pyruvic acid | list9 = AND (pharmacogenomics)}} Genetics of Pyruvic acidAND (pharmacogenomics)}} Pharmacogenomics of Pyruvic acidAND (proteomics)}} Proteomics of Pyruvic acid


| group10 = Newstories on Pyruvic acid | list10 = Pyruvic acid in the newsBe alerted to news on Pyruvic acidNews trends on Pyruvic acid</small>


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| group13 = Healthcare Provider Resources on Pyruvic acid | list13 = Symptoms of Pyruvic acidCauses & Risk Factors for Pyruvic acidDiagnostic studies for Pyruvic acidTreatment of Pyruvic acid

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