Decarboxylation
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Decarboxylation is any chemical reaction in which a carboxyl group (-COOH) is split off from a compound as carbon dioxide (CO2).
In biochemistry
Common biosynthetic decarboxylations of amino acids to amines are:
- tryptophan to tryptamine
- phenylalanine to phenylethylamine
- tyrosine to tyramine
- histidine to histamine
- serine to ethanolamine
- glutamic acid to GABA
- lysine to cadaverine
- arginine to agmatine
- ornithine to putrescine
- 5-HTP to serotonin
- L-DOPA to dopamine
Other decarboxylation reactions from the citric acid cycle include:
- pyruvate to acetyl-CoA
- oxalosuccinate to α-ketoglutarate
- α-ketoglutarate to succinyl-CoA.
Enzymes that catalyze decarboxylations are called decarboxylases or, more formally, carboxy-lyases (EC number 4.1.1).
In organic chemistry
Chemical decarboxylations reactions often require extensive heating in high-boiling solvents. Copper salts are often added as catalysts. Also the addition of catalytic amounts of cyclohexen-2-one has been reported to catalyze the decarboxylation of amino acids. Decarboxylations are especially easy for beta-keto acids due to the formation of a cyclic transition state for instance in Knoevenagel condensations. The Barton decarboxylation and Hunsdiecker reaction are radical reactions.
See also
it:Decarbossilazione nl:Decarboxylering ja:脱炭酸 sv:Dekarboxylering
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