Phenylpyruvic acid is the
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with the formula C
6H
5CH
2C(O)CO
2H. It is a
keto acid
In organic chemistry, keto acids or ketoacids (also called oxo acids or oxoacids) are organic compounds that contain a carboxylic acid group () and a ketone group ().Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's En ...
.
Occurrence and properties
The compound exists in equilibrium with its E- and Z-enol tautomers. It is a product from the
oxidative deamination of
phenylalanine.
When the activity of the enzyme
phenylalanine hydroxylase
Phenylalanine hydroxylase. (PAH) () is an enzyme that catalyzes the hydroxylation of the aromatic side-chain of phenylalanine to generate tyrosine. PAH is one of three members of the biopterin-dependent aromatic amino acid hydroxylases, a class ...
is reduced, the
amino acid
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha a ...
phenylalanine accumulates and gets converted into phenylpyruvic acid (phenylpyruvate), which leads to
Phenylketonuria (PKU).
Preparation and reactions
It can be prepared by many methods. Classically it is produced from aminocinnamic acid derivatives. It has been prepared by condensation of
benzaldehyde and
glycine
Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid ( carbamic acid is unstable), with the chemical formula NH2‐ CH2‐ COOH. Glycine is one of the proteinog ...
derivatives to give phenylazlactone, which is then hydrolyzed with acid- or base-catalysis. It can also be synthesized from
benzyl chloride by double
carbonylation
Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbony ...
.
Reductive amination
Reductive amination (also known as reductive alkylation) is a form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is considered ...
of phenylpyruvic acid gives
phenylalanine.
See also
*
Phenylpyruvate decarboxylase
*
Phenylpyruvate tautomerase
*
Phenylketonuria
Phenylketonuria (PKU) is an inborn error of metabolism that results in decreased metabolism of the amino acid phenylalanine. Untreated PKU can lead to intellectual disability, seizures, behavioral problems, and mental disorders. It may also re ...
References
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Alpha-keto acids
Benzyl compounds