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Chlorohydrin Hepatic fatty acid conjugation

Time:2015/11/25 8:12:24

Degradation of chlorohydrin by wild type and mutants of Pseudomonas putida US2


A strain of Pseudomonas putida was isolated that was able to degrade chlorohydrin. The degradation proceeded via 2-chloroacetaldehyde and chloroacetate to glycolate. In crude extracts the enzymes for this degradation pathway could be detected. All enzymes proved to be inducible. The dehalogenase that catalyzed the dehalogenation of chloroacetate to glycolate was further characterized. It consisted of a single polypeptide chain with a molecular mass of 28 kDa. After induction the dehalogenase was expressed at a high level. In a mutant resistant to high concentrations of chlorohydrin the dehalogenase was no longer expressed. The mechanism of resistance seemed to be due to the inability to convert chloroacetate and export of this compound out of the cell.


Hepatic fatty acid conjugation of chlorohydrin and 2-bromoethanol in rats


To study the formation of fatty acid conjugates of chlorohydrin (2-CE) and 2-bromoethanol (2-BE), rats were administered (by gavage) 50 mg/kg of 2-CE and 2-BE in mineral oil and sacrificed on fifth day of the treatment. Hepatic microsomal lipids were extracted, and the fatty acid esters were separated by preparative thin-layer chromotography. The ester fraction was further purified by reverse-phase, high-performance liquid chromatography and analyzed by ammonia chemical ionization mass spectrometry. Pseudomolecular ions (M + NH4+, base peak) at m/z 336/338, 362/364, and 364/366 in a ratio of 3:1 and 380/382 and 408/410 in a ratio of 1:1 confirmed the in vivo formation of 2-chloroethyl palmitate, 2-chloroethyl oleate, 2-chloroethyl stearate, 2-bromoethyl palmitate, and 2-bromoethyl stearate, respectively. These results demonstrate the formation of fatty acid conjugates of 2-CE and 2-BE in vivo. These fatty acid conjugates may be retained in the body for a longer time and cause toxic manifestations.