3-Amino-1,2,4-triazole
Encyclopedia
3-Amino-1,2,4-triazole (3-AT) is a heterocyclic
organic compound
that consists of a 1,2,4-triazole
substituted with an amino group
.
3-AT is a competitive inhibitor of the product of the HIS3
gene, imidazoleglycerol-phosphate dehydratase
. Imidazoleglycerol-phosphate dehydratase is an enzyme catalysing the sixth step of histidine production.
3-AT is also is a nonselective systemic triazole
herbicide
used on nonfood croplands to control annual grasses and broadleaf and aquatic weed
s. It is not used on food
crops
because of its carcinogenic properties. As an herbicide, it is known as aminotriazole, amitrole or amitrol.
Amitrol was included in a biocide ban proposed by the Swedish Chemicals Agency and approved by the European Parliament on January 13, 2009.
which is dependent upon a plasmid containing HIS3 to produce histidine
(i.e. its own HIS3 analogue is not present or nonfunctional), an increased level of HIS3 expression is required in order for the yeast cell to survive. This has proved useful in various two-hybrid system, where a high affinity binding between two proteins (i.e., higher expression of the HIS3 gene) will allow the yeast cell to survive in media containing higher concentrations of 3-AT. Of course this selection process is performed using selective media, containing no histidine.
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....
organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
that consists of a 1,2,4-triazole
1,2,4-Triazole
1,2,4-Triazole is one of a pair of isomeric chemical compounds with molecular formula C2H3N3, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms. 1,2,4-Triazole is a basic aromatic heterocycle...
substituted with an amino group
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
.
3-AT is a competitive inhibitor of the product of the HIS3
HIS3
The HIS3 gene, found in the Saccharomyces cerevisiae yeast, encodes a protein called Imidazoleglycerol-phosphate dehydratase which catalyses the sixth step in histidine biosynthesis...
gene, imidazoleglycerol-phosphate dehydratase
Imidazoleglycerol-phosphate dehydratase
In enzymology, an imidazoleglycerol-phosphate dehydratase is an enzyme that catalyzes the chemical reactionHence, this enzyme has one substrate, D-erythro-1-glycerol 3-phosphate, and two products, 3--2-oxopropyl phosphate and H2O.This enzyme belongs to the family of lyases, specifically the...
. Imidazoleglycerol-phosphate dehydratase is an enzyme catalysing the sixth step of histidine production.
3-AT is also is a nonselective systemic triazole
Triazole
Triazole refers to either one of a pair of isomeric chemical compounds with molecular formula C2H3N3, having a five-membered ring of two carbon atoms and three nitrogen atoms.The two isomers are:*1,2,3-Triazole 100px*1,2,4-Triazole 100px...
herbicide
Herbicide
Herbicides, also commonly known as weedkillers, are pesticides used to kill unwanted plants. Selective herbicides kill specific targets while leaving the desired crop relatively unharmed. Some of these act by interfering with the growth of the weed and are often synthetic "imitations" of plant...
used on nonfood croplands to control annual grasses and broadleaf and aquatic weed
Weed
A weed in a general sense is a plant that is considered by the user of the term to be a nuisance, and normally applied to unwanted plants in human-controlled settings, especially farm fields and gardens, but also lawns, parks, woods, and other areas. More specifically, the term is often used to...
s. It is not used on food
Food
Food is any substance consumed to provide nutritional support for the body. It is usually of plant or animal origin, and contains essential nutrients, such as carbohydrates, fats, proteins, vitamins, or minerals...
crops
Crop (agriculture)
A crop is a non-animal species or variety that is grown to be harvested as food, livestock fodder, fuel or for any other economic purpose. Major world crops include maize , wheat, rice, soybeans, hay, potatoes and cotton. While the term "crop" most commonly refers to plants, it can also include...
because of its carcinogenic properties. As an herbicide, it is known as aminotriazole, amitrole or amitrol.
Amitrol was included in a biocide ban proposed by the Swedish Chemicals Agency and approved by the European Parliament on January 13, 2009.
Exploits
By applying 3-AT to a yeast cell cultureCell culture
Cell culture is the complex process by which cells are grown under controlled conditions. In practice, the term "cell culture" has come to refer to the culturing of cells derived from singlecellular eukaryotes, especially animal cells. However, there are also cultures of plants, fungi and microbes,...
which is dependent upon a plasmid containing HIS3 to produce histidine
Histidine
Histidine Histidine, an essential amino acid, has a positively charged imidazole functional group. It is one of the 22 proteinogenic amino acids. Its codons are CAU and CAC. Histidine was first isolated by German physician Albrecht Kossel in 1896. Histidine is an essential amino acid in humans...
(i.e. its own HIS3 analogue is not present or nonfunctional), an increased level of HIS3 expression is required in order for the yeast cell to survive. This has proved useful in various two-hybrid system, where a high affinity binding between two proteins (i.e., higher expression of the HIS3 gene) will allow the yeast cell to survive in media containing higher concentrations of 3-AT. Of course this selection process is performed using selective media, containing no histidine.