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Oxaloacetic acid
 
 
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Oxaloacetic acid is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the chemical formula HO2CC(O)CH2CO2H. It also has other names (see Table) and its conjugate base is called "oxaloacetate." This four-carbon
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
 dicarboxylic acid
Dicarboxylic acid

Dicarboxylic acids are organic compounds that are substituted with two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R is usually an alkane, alkene, or alkyne group....
 is a protonated variant of oxaloacetate, which is an intermediate of the citric acid cycle
Citric acid cycle

The citric acid cycle ? also known as the tricarboxylic acid cycle ; the Krebs cycle; or, more rarely, the Szent-Gy?rgyi-Krebs cycle) ? is a series of enzyme-catalysed chemical reactions of central importance in all living cell s that use oxygen as part of cellular respiration....
 and gluconeogenesis
Gluconeogenesis

Gluconeogenesis is a metabolic pathway that results in the generation of glucose from non-carbohydrate carbon substrates such as lactic acid, glycerol, and glucogenic amino acids....
. Oxaloacetate forms upon oxidation of L-malate
Malic acid

Malic acid is an organic compound with the formula HO2CCH2CHOHCO2H. This dicarboxylic acid is the active ingredient in many sour or tart foods....
, catalysed by malate dehydrogenase
Malate dehydrogenase

Malate dehydrogenase is an enzyme in the citric acid cycle that catalysis the conversion of malate into oxaloacetate and vice versa . Malate dehydrogenase is not to be confused with malic enzyme, which catalyzes the conversion of malate to pyruvate producing NADPH....
, and reacts with Acetyl-CoA
Acetyl-CoA

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 the citric acid cycle to be oxidation for energy production....
 to form citrate
Citrate

A citrate can refer either to the conjugate base of citric acid, , or to the esters of citric acid. An example of the former, a salt is trisodium citrate; an ester is triethyl citrate....
, catalysed by citrate synthase
Citrate synthase

The enzyme citrate synthase exists in nearly all living cells and stands as a pace-making enzyme in the first step of the Citric Acid Cycle . Citrate synthase is localized within eukaryotic cells in the mitochondrial matrix, but is encoded by nuclear DNA rather than mitochondrial....
.






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Oxaloacetic acid is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 with the chemical formula HO2CC(O)CH2CO2H. It also has other names (see Table) and its conjugate base is called "oxaloacetate." This four-carbon
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
 dicarboxylic acid
Dicarboxylic acid

Dicarboxylic acids are organic compounds that are substituted with two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R is usually an alkane, alkene, or alkyne group....
 is a protonated variant of oxaloacetate, which is an intermediate of the citric acid cycle
Citric acid cycle

The citric acid cycle ? also known as the tricarboxylic acid cycle ; the Krebs cycle; or, more rarely, the Szent-Gy?rgyi-Krebs cycle) ? is a series of enzyme-catalysed chemical reactions of central importance in all living cell s that use oxygen as part of cellular respiration....
 and gluconeogenesis
Gluconeogenesis

Gluconeogenesis is a metabolic pathway that results in the generation of glucose from non-carbohydrate carbon substrates such as lactic acid, glycerol, and glucogenic amino acids....
. Oxaloacetate forms upon oxidation of L-malate
Malic acid

Malic acid is an organic compound with the formula HO2CCH2CHOHCO2H. This dicarboxylic acid is the active ingredient in many sour or tart foods....
, catalysed by malate dehydrogenase
Malate dehydrogenase

Malate dehydrogenase is an enzyme in the citric acid cycle that catalysis the conversion of malate into oxaloacetate and vice versa . Malate dehydrogenase is not to be confused with malic enzyme, which catalyzes the conversion of malate to pyruvate producing NADPH....
, and reacts with Acetyl-CoA
Acetyl-CoA

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 the citric acid cycle to be oxidation for energy production....
 to form citrate
Citrate

A citrate can refer either to the conjugate base of citric acid, , or to the esters of citric acid. An example of the former, a salt is trisodium citrate; an ester is triethyl citrate....
, catalysed by citrate synthase
Citrate synthase

The enzyme citrate synthase exists in nearly all living cells and stands as a pace-making enzyme in the first step of the Citric Acid Cycle . Citrate synthase is localized within eukaryotic cells in the mitochondrial matrix, but is encoded by nuclear DNA rather than mitochondrial....
. It also forms in the mesophyll of plants by the condensation of CO2
Carbon dioxide

Carbon dioxide is a chemical compound composed of two oxygen atoms covalent bond to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state....
 with phosphoenolpyruvate
Phosphoenolpyruvate

Phosphoenolpyruvic acid , or phosphoenolpyruvate as the anion, is an important chemical compound in biochemistry. It has the high-energy phosphate bond found in living organisms, and is involved in glycolysis and gluconeogenesis....
, catalysed by PEP Carboxykinase
Phosphoenolpyruvate carboxykinase

Phosphoenolpyruvate carboxykinase is an enzyme used in the natural process of gluconeogenesis. It converts oxaloacetate into phosphoenolpyruvate and carbon dioxide....
. It can arise from pyruvate via an anaplerotic reaction
Anaplerotic reactions

Anaplerotic:Ana-up,Plerotikos-to fillAnaplerotic 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....
.

The enol
Enol

Enols are alkenes with a hydroxyl group affixed to one of the carbon atoms composing the double bond. Enols and carbonyl compounds are in fact isomers; this is called keto-enol tautomerism:...
 forms of oxaloacetic acid are particularly stable, so much so that the two isomers have different melting points (152 °C cis, 184 °C trans). The enol proton has a pKa value
Acid dissociation constant

An acid dissociation constant, Ka, is a quantitative measure of the strong acid in solution. It is the equilibrium constant for a chemical reaction known as Dissociation in the context of acid-base reactions....
 of 13.02. The enzyme
Enzyme

Enzymes are biomolecules that catalysis chemical reactions. Almost all enzymes are proteins. In enzymatic reactions, the molecules at the beginning of the process are called Substrate , and the enzyme converts them into different molecules, the products....
 fumarase
Fumarase

Fumarase is an enzyme that catalyzes the reversible hydration/dehydration of Fumarate to S-malate. Fumarase comes in two forms: mitochondrial and cytosolic....
 A from E. coli
Escherichia coli

'Escherichia coli' , is a Gram negative bacterium that is commonly found in the lower gastrointestinal tract of warm-blooded animals. Most E....
 catalyses the conversion between the keto and enol forms.

Oxaloacetate is unstable in solution, decomposing to pyruvate by decarboxylation
Decarboxylation

Decarboxylation is any chemical reaction in which a carboxyl group is split off from a compound as carbon dioxide ....
 over a period of hours (room temperature) or days (0 °C). Refrigerated storage of the solid is therefore recommended.