Commandeur L C, Parsons J R
Department of Environmental and Toxicological Chemistry, University of Amsterdam, The Netherlands.
Biodegradation. 1990;1(2-3):207-20. doi: 10.1007/BF00058837.
Due to their persistence, haloaromatics are compounds of environmental concern. Aerobically, bacteria degrade these compounds by mono- or dioxygenation of the aromatic ring. The common intermediate of these reactions is (halo)catechol. Halocatechol is cleaved either intradiol (ortho-cleavage) or extradiol (meta-cleavage). In contrast to ortho-cleavage, meta-cleavage of halocatechols yields toxic metabolites. Dehalogenation may occur fortuitously during oxygenation. Specific dehalogenation of aromatic compounds is performed by hydroxylases, in which the halo-substituent is replaced by a hydroxyl group. During reductive dehalogenation, haloaromatic compounds may act as electron-acceptors. Herewith, the halosubstituent is replaced by a hydrogen atom.
由于其持久性,卤代芳烃是受环境关注的化合物。在有氧条件下,细菌通过芳香环的单加氧或双加氧作用降解这些化合物。这些反应的常见中间体是(卤代)儿茶酚。卤代儿茶酚通过二醇内(邻位裂解)或二醇外(间位裂解)进行裂解。与邻位裂解不同,卤代儿茶酚的间位裂解会产生有毒代谢物。脱卤可能在氧化过程中偶然发生。芳香化合物的特异性脱卤由羟化酶进行,其中卤代取代基被羟基取代。在还原性脱卤过程中,卤代芳烃化合物可作为电子受体。由此,卤代取代基被氢原子取代。