Taylor B F, Amador J A, Levinson H S
Division of Marine and Atmospheric Chemistry, Rosenstiel School of Marine and Atmospheric Science, University of Miami, FL 33149-1098.
FEMS Microbiol Lett. 1993 Jun 15;110(2):213-6. doi: 10.1111/j.1574-6968.1993.tb06322.x.
m- and p-trifluoromethyl (TFM)-benzoates are incompletely degraded by aerobic bacteria that catabolize alkylbenzoates; biodegradation ceases after ring-fission with the accumulation of a trifluoromethyl muconate semialdehyde (2-hydroxy-6-oxo-7,7,7-trifluorohepta-2,4-dienoate, TFHOD) which is resistant to biochemical attack. A bacterium (Strain V-1), isolated from sea-water, grew aerobically on benzoate or m-toluate. Cells grown on benzoate or m-toluate oxidized both compounds at similar relative rates. Catabolism involved benzoate 1,2-dioxygenase (decarboxylating) and meta-cleavage to yield muconate semialdehydes. Cells grown on benzoate metabolized m-TFM-benzoate to TFHOD. The ring-fission products from m-toluate and TFHOD were degraded by sunlight, and equimolar fluoride was released from TFHOD. Sequential biochemical and photochemical treatment allowed the destruction of m-TFM-benzoate beyond the biochemically recalcitrant intermediate TFHOD.
间位和对位三氟甲基（TFM）苯甲酸酯不能被分解代谢烷基苯甲酸酯的需氧细菌完全降解；在与对生物化学攻击具有抗性的三氟甲基粘康酸半醛（2-羟基-6-氧代-7,7,7-三氟庚-2,4-二烯酸酯，TFHOD）发生环裂变并积累后，生物降解停止。从海水中分离出的一种细菌（菌株V-1）在苯甲酸酯或间甲苯酸酯上进行需氧生长。在苯甲酸酯或间甲苯酸酯上生长的细胞以相似的相对速率氧化这两种化合物。分解代谢涉及苯甲酸1,2-双加氧酶（脱羧）和间位裂解以产生粘康酸半醛。在苯甲酸酯上生长的细胞将间位TFM-苯甲酸酯代谢为TFHOD。间甲苯酸酯和TFHOD的环裂变产物被阳光降解，并且从TFHOD中释放出等摩尔的氟化物。连续的生化和光化学处理使得间位TFM-苯甲酸酯的破坏超出了生物化学上难降解的中间体TFHOD。
