Names | |
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IUPAC name 1H-1,2,4-Triazol-3-amine | |
Other names 1,2,4-Triazol-3-amine aminotriazole Amitrol Amitrole 3-Aminotriazole 2-Amino-1,3,4-triazole | |
Identifiers | |
3D model (JSmol) | |
Abbreviations | 3-AT |
107687 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.000.474 |
EC Number |
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200706 | |
KEGG | |
MeSH | Amitrole |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C2H4N4 | |
Molar mass | 84.082 g·mol−1 |
Appearance | colorless/white crystals or powder [2] |
Odor | odorless |
Density | 1.138 g/mL |
Melting point | 157 to 159 °C (315 to 318 °F; 430 to 432 K) |
Boiling point | 347 |
28 g/100 mL | |
Solubility | soluble in acetonitrile, chloroform, ethanol, methanol, methylene chloride negligible in ethyl acetate |
Vapor pressure | 3.13x10−9 mmHg |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | potential occupational carcinogen |
GHS labelling: | |
Warning | |
H361, H373, H411 | |
P201, P202, P260, P273, P281, P308+P313, P314, P391, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | Non-flammable |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 1,100 to 2,500 mg/kg |
NIOSH (US health exposure limits): | |
PEL (Permissible) | none [2] |
REL (Recommended) | Ca TWA 0.2 mg/m3 [2] |
IDLH (Immediate danger) | Ca/N.D. [2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
3-Amino-1,2,4-triazole (3-AT) is a heterocyclic organic compound that consists of 1,2,4-triazole with an amino group as a substituent.
3-AT is a competitive inhibitor of the product of the HIS3 gene, imidazoleglycerol-phosphate dehydratase. [3] [4] Imidazoleglycerol-phosphate dehydratase is an enzyme catalyzing the sixth step of histidine production. [5]
3-AT is also a nonselective systemic triazole herbicide used on nonfood croplands to control annual grasses and broadleaf and aquatic weeds. 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 [6] and approved by the European Parliament on January 13, 2009. [7] Amitrol's mode of action is unknown, though it is classed as a resistance group Q herbicide. [8]
By applying 3-AT to a yeast cell culture 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. This selection process is performed using selective media, containing no histidine.
On November 9, 1959, the secretary of the United States Department of Health, Education, and Welfare, Arthur S. Flemming, announced that some of the 1959 cranberry crop was tainted with traces of the herbicide aminotriazole. [9] The market for cranberries collapsed and growers lost millions of dollars. [10] However, Ocean Spray recovered by expanding the market for cranberry juice, which, although widely available for sale, was before then not popular. This ensured cranberry growers would not have to rely mostly on Thanksgiving and Christmas for sales, which was the case until the 1959 incident.
A protein kinase is a kinase which selectively modifies other proteins by covalently adding phosphates to them (phosphorylation) as opposed to kinases which modify lipids, carbohydrates, or other molecules. Phosphorylation usually results in a functional change of the target protein (substrate) by changing enzyme activity, cellular location, or association with other proteins. The human genome contains about 500 protein kinase genes and they constitute about 2% of all human genes. There are two main types of protein kinase. The great majority are serine/threonine kinases, which phosphorylate the hydroxyl groups of serines and threonines in their targets. Most of the others are tyrosine kinases, although additional types exist. Protein kinases are also found in bacteria and plants. Up to 30% of all human proteins may be modified by kinase activity, and kinases are known to regulate the majority of cellular pathways, especially those involved in signal transduction.
In biochemistry, phosphorylation is the attachment of a phosphate group to a molecule or an ion. This process and its inverse, dephosphorylation, are common in biology. Protein phosphorylation often activates many enzymes.
Histidine (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –NH3+ form under biological conditions), a carboxylic acid group (which is in the deprotonated –COO− form under biological conditions), and an imidazole side chain (which is partially protonated), classifying it as a positively charged amino acid at physiological pH. Initially thought essential only for infants, it has now been shown in longer-term studies to be essential for adults also. It is encoded by the codons CAU and CAC.
Auxotrophy is the inability of an organism to synthesize a particular organic compound required for its growth. An auxotroph is an organism that displays this characteristic; auxotrophic is the corresponding adjective. Auxotrophy is the opposite of prototrophy, which is characterized by the ability to synthesize all the compounds needed for growth.
Pyridoxal phosphate (PLP, pyridoxal 5'-phosphate, P5P), the active form of vitamin B6, is a coenzyme in a variety of enzymatic reactions. The International Union of Biochemistry and Molecular Biology has catalogued more than 140 PLP-dependent activities, corresponding to ~4% of all classified activities. The versatility of PLP arises from its ability to covalently bind the substrate, and then to act as an electrophilic catalyst, thereby stabilizing different types of carbanionic reaction intermediates.
Two-hybrid screening is a molecular biology technique used to discover protein–protein interactions (PPIs) and protein–DNA interactions by testing for physical interactions between two proteins or a single protein and a DNA molecule, respectively.
A triazole is a heterocyclic compound featuring a five-membered ring of two carbon atoms and three nitrogen atoms with molecular formula C2H3N3. Triazoles exhibit substantial isomerism, depending on the positioning of the nitrogen atoms within the ring.
The enzyme histidine decarboxylase is transcribed on chromosome 15, region q21.1-21.2, and catalyzes the decarboxylation of histidine to form histamine. In mammals, histamine is an important biogenic amine with regulatory roles in neurotransmission, gastric acid secretion and immune response. Histidine decarboxylase is the sole member of the histamine synthesis pathway, producing histamine in a one-step reaction. Histamine cannot be generated by any other known enzyme. HDC is therefore the primary source of histamine in most mammals and eukaryotes. The enzyme employs a pyridoxal 5'-phosphate (PLP) cofactor, in similarity to many amino acid decarboxylases. Eukaryotes, as well as gram-negative bacteria share a common HDC, while gram-positive bacteria employ an evolutionarily unrelated pyruvoyl-dependent HDC. In humans, histidine decarboxylase is encoded by the HDC gene.
Amino acid biosynthesis is the set of biochemical processes by which the amino acids are produced. The substrates for these processes are various compounds in the organism's diet or growth media. Not all organisms are able to synthesize all amino acids. For example, humans can synthesize 11 of the 20 standard amino acids. These 11 are called the non-essential amino acids.
The HIS3 gene, found in the Saccharomyces cerevisiae yeast, encodes a protein called Imidazoleglycerol-phosphate dehydratase which catalyses the sixth step in histidine biosynthesis. It is analogous to hisB in Escherichia coli.
The hisB gene, found in the enterobacteria, in Campylobacter jejuni and in Xylella/Xanthomonas encodes a protein involved in catalysis of two step in histidine biosynthesis, namely the bifunctional Imidazoleglycerol-phosphate dehydratase/histidinol-phosphatase.
HIS-selective medium is a type cell culture medium that lacks the amino acid histidine. It can be used with bacteria reliant on the expression of a gene encoding proteins involved in histidine expression in order to survive. Only bacteria expressing such genes will survive on these media.
The enzyme 3-dehydroquinate dehydratase (EC 4.2.1.10) catalyzes the chemical reaction
The enzyme imidazoleglycerol-phosphate dehydratase (EC 4.2.1.19) catalyzes the chemical reaction
In molecular biology, a two-component regulatory system serves as a basic stimulus-response coupling mechanism to allow organisms to sense and respond to changes in many different environmental conditions. Two-component systems typically consist of a membrane-bound histidine kinase that senses a specific environmental stimulus, and a corresponding response regulator that mediates the cellular response, mostly through differential expression of target genes. Although two-component signaling systems are found in all domains of life, they are most common by far in bacteria, particularly in Gram-negative and cyanobacteria; both histidine kinases and response regulators are among the largest gene families in bacteria. They are much less common in archaea and eukaryotes; although they do appear in yeasts, filamentous fungi, and slime molds, and are common in plants, two-component systems have been described as "conspicuously absent" from animals.
The bacterial one-hybrid (B1H) system is a method for identifying the sequence-specific target site of a DNA-binding domain. In this system, a given transcription factor (TF) is expressed as a fusion to a subunit of RNA polymerase. In parallel, a library of randomized oligonucleotides representing potential TF target sequences are cloned into a separate vector containing the selectable genes HIS3 and URA3. If the DNA-binding domain (bait) binds a potential DNA target site (prey) in vivo, it will recruit RNA polymerase to the promoter and activate transcription of the reporter genes in that clone. The two reporter genes, HIS3 and URA3, allow for positive and negative selections, respectively. At the end of the process, positive clones are sequenced and examined with motif-finding tools in order to resolve the favoured DNA target sequence.
5-enolpyruvylshikimate-3-phosphate (EPSP) synthase is an enzyme produced by plants and microorganisms. EPSPS catalyzes the chemical reaction:
Metribuzin is a herbicide used both pre- and post-emergence in crops including soy bean, potatoes, tomatoes and sugar cane.
Early twenty-first century pesticide research has focused on developing molecules that combine low use rates and that are more selective, safer, resistance-breaking and cost-effective. Obstacles include increasing pesticide resistance and an increasingly stringent regulatory environment.
Chromosome 21 Open Reading Frame 58 (C21orf58) is a protein that in humans is encoded by the C21orf58 gene.