aromatic-hydroxylamine O-acetyltransferase | |||||||||
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Identifiers | |||||||||
EC no. | 2.3.1.56 | ||||||||
CAS no. | 52660-15-8 | ||||||||
Databases | |||||||||
IntEnz | IntEnz view | ||||||||
BRENDA | BRENDA entry | ||||||||
ExPASy | NiceZyme view | ||||||||
KEGG | KEGG entry | ||||||||
MetaCyc | metabolic pathway | ||||||||
PRIAM | profile | ||||||||
PDB structures | RCSB PDB PDBe PDBsum | ||||||||
Gene Ontology | AmiGO / QuickGO | ||||||||
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In enzymology, an aromatic-hydroxylamine O-acetyltransferase (EC 2.3.1.56) is an enzyme that catalyzes the chemical reaction
Thus, the two substrates of this enzyme are N-hydroxy-4-acetylaminobiphenyl and N-hydroxy-4-aminobiphenyl, whereas its two products are N-hydroxy-4-aminobiphenyl and N-acetoxy-4-aminobiphenyl.
This enzyme belongs to the family of transferases, specifically those acyltransferases transferring groups other than aminoacyl groups. The systematic name of this enzyme class is N-hydroxy-4-acetylaminobiphenyl:N-hydroxy-4-aminobiphenyl O-acetyltransferase. Other names in common use include aromatic hydroxylamine acetyltransferase, arylhydroxamate acyltransferase, arylhydroxamate N,O-acetyltransferase, arylhydroxamic acid N,O-acetyltransferase, arylhydroxamic acyltransferase, N,O-acetyltransferase, and N-hydroxy-2-acetylaminofluorene N-O acyltransferase.
4-Aminobiphenyl (4-APB) is an organic compound with the formula C6H5C6H4NH2. It is an amine derivative of biphenyl. It is a colorless solid, although aged samples can appear colored. 4-Aminobiphenyl was commonly used in the past as a rubber antioxidant and an intermediate for dyes. Exposure to this aryl-amine can happen through contact with chemical dyes and from inhalation of cigarette smoke. Researches showed that 4-aminobiphenyl is responsible for bladder cancer in humans and dogs by damaging DNA. Due to its carcinogenic effects, commercial production of 4-aminobiphenyl ceased in the United States in the 1950s.
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2-Acetylaminofluorene is a carcinogenic and mutagenic derivative of fluorene. It is used as a biochemical tool in the study of carcinogenesis. It induces tumors in a number of species in the liver, bladder and kidney. The metabolism of this compound in the body by means of biotransformation reactions is the key to its carcinogenicity. 2-AAF is a substrate for cytochrome P-450 (CYP) enzyme, which is a part of a super family found in almost all organisms. This reaction results in the formation of hydroxyacetylaminofluorene which is a proximal carcinogen and is more potent than the parent molecule. The N-hydroxy metabolite undergoes several enzymatic and non-enzymatic rearrangements. It can be O-acetylated by cytosolic N-acetyltransferase enzyme to yield N-acetyl-N-acetoxyaminofluorene. This intermediate can spontaneously rearrange to form the arylamidonium ion and a carbonium ion which can interact directly with DNA to produce DNA adducts. In addition to esterification by acetylation, the N-hydroxy derivative can be O-sulfated by cytosolic sulfur transferase enzyme giving rise to the N-acetyl-N-sulfoxy product.