Thiazoline
Encyclopedia
Thiazoline is a heterocyclic compound
containing both sulfur and nitrogen in the ring. Although thiazoline itself is rarely encountered, its derivatives are often bioactive. For example, in a common post-translational modification, cysteine residues are converted into thiazolines.
of thioamide
s. More commonly, they are prepared from derivatives of 2-aminoethanethiol (cysteamine
).
, the light-emitting molecule in fireflies
. The amino acid cysteine
is produced industrially from substituted thiazole.
Heterocyclic compound
A heterocyclic compound is a cyclic compound which has atoms of at least two different elements as members of its ring. The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element....
containing both sulfur and nitrogen in the ring. Although thiazoline itself is rarely encountered, its derivatives are often bioactive. For example, in a common post-translational modification, cysteine residues are converted into thiazolines.
Synthesis
Thiazolines were first prepared by dialkylationAlkylation
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene . Alkylating agents are widely used in chemistry because the alkyl group is probably the most common group encountered in...
of thioamide
Thioamide
Thioamide is a functional group with the general structure R-CS-NR'R, where R, R', and R are organic groups. They are analogous to amides but they exhibit greater multiple bond character along the C-N bond, resulting in a larger rotational barrier...
s. More commonly, they are prepared from derivatives of 2-aminoethanethiol (cysteamine
Cysteamine
Cysteamine is the chemical compound with the formula HSCH2CH2NH2. It is the simplest stable aminothiol and a degradation product of the amino acid cysteine. It is often used as the hydrochloride salt, HSCH2CH2NH3Cl....
).
Related compounds
Three related classes of C3NS heterocycles are well studied, 1,3-thiazoles (parent: C3H3NS), 1,3-thiazolines (parent: C3H5NS), and 1,3-thiazolidines (parent: C3H7NS). The naming is analogous to the C3N2 heterocycles, imidazoles, imidazolines, and imidazolidines.Substituted thiazolines
Many molecules contain thiazoline rings, one example being luciferinLuciferin
Luciferins are a class of light-emitting biological pigments found in organisms that cause bioluminescence...
, the light-emitting molecule in fireflies
Fireflies
Fireflies is a novel by Shiva Naipaul originally published in 1970. It was his first book, a comic novel set in Trinidad. In an essay in An Unfinished Journey, Naipaul described how in 1968 as a final year student at Oxford University studying Chinese, he had been moved to write down a sentence,...
. The amino acid cysteine
Cysteine
Cysteine is an α-amino acid with the chemical formula HO2CCHCH2SH. It is a non-essential amino acid, which means that it is biosynthesized in humans. Its codons are UGU and UGC. The side chain on cysteine is thiol, which is polar and thus cysteine is usually classified as a hydrophilic amino acid...
is produced industrially from substituted thiazole.