DL-треонин

Описание

Threonine (abbreviated as Thr or T) is an α-amino acid with the chemical formula HO2CCH(NH2)CH(OH)CH3. Its codons are ACU, ACA, ACC, and ACG. This essential amino acid is classified as polar. Together with serine, threonine is one of two proteinogenic amino acids bearing an alcohol group (tyrosine is not an alcohol but a phenol, since its hydroxyl group is bonded directly to an aromatic ring, giving it different acid/base and oxidative properties). It is also one of two common amino acids that bear a chiral side chain, along with isoleucine.
The threonine residue is susceptible to numerous posttr anslational modifications. The hydroxy side-chain can undergo Olinked glycosylation. In addition, threonine residues undergo phospho rylation through the action of a threonine kinase. In its phosphorylated form, it can be referred to as phospho threonine.

Химические свойства

White crystalline powder

Вхождение

Foods high in threonine include cottage cheese, poultry, fish, meat, lentils, Black turtle bean and Sesame seeds.
Racemic threonine can be prepared from crotonic acid by alphafunctionalization using mercury (II) acetate.

История

Threonine was discovered as the last of the 20 common proteinogenic amino acids in the 1930s by William Cumming Rose.

Использование

DL-Threonine is used as a polar essential amino acid. It serves as a precursor of glycine as well as used in the biosynthesis of proteins. Further, it is used for biochemical research. In addition to this, it is used as a nutrition enhancer.

Биосинтез

As an essential amino acid, threonine is not synthesized in humans, hence we must ingest threonine in the form of threoninecontaining proteins. In plants and microorganisms, threonine is synthesized from aspartic acid via α-aspartyl-semialdehyde and homoserine. Homoserine undergoes O-phosphorylation; this phosphate ester undergoes hydrolysis concomitant with relocation of the OH group. Enzymes involved in a typical biosynthesis of threonine include :
aspartokinase
β-aspartate semialdehyde dehydrogenase
homoserine dehydrogenase
homoserine kinase
threonine synthase.

Метаболизм

Threonine is metabolized in two ways:
It is converted to pyruvate via threonine dehydrogenase. An intermediate in this pathway can undergo thiolysis with CoA to produce acetyl-CoA and glycine.
In humans, it is converted to α-ketobutyrate in a less common pathway via the enzyme serine dehydratase, and thereby enters the pathway leading to succinyl-CoA.
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