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Novel phosphorylation of aldrin-trans-diol by dieldrin-degrading fungus Mucor racemosus strain DDF

2014; Elsevier BV; Volume: 92; Linguagem: Inglês

10.1016/j.ibiod.2014.04.005

1879-0208

Ken Yamazaki, Kazuhiro Takagi, Ryota Kataoka, Masaaki Kotake, Teiko Yamada, Hiromasa Kiyota,

Microbial bioremediation and biosurfactants

Dieldrin is one of the most persistent organic pollutants, and its oxidative degradation pathways by aerobic microorganisms to 6,7-trans-dihydroxydihydroaldrin (otherwise known as aldrin-trans-diol) and 9-hydroxydieldrin are well documented. The dieldrin-degrading fungus, Mucor racemosus strain DDF, can decrease dieldrin levels with simultaneous production of a small amount of aldrin-trans-diol. A reduction in the levels of aldrin-trans-diol by strain DDF has also been observed. Based on these results, it has been suggested that strain DDF transforms dieldrin to more polar compounds via aldrin-trans-diol. We have conducted a study to identify the metabolites arising from aldrin-trans-diol. The results showed that strain DDF gave reduced levels of aldrin-trans-diol and also produced unknown metabolites. Ultra performance liquid chromatography-electrospray ionization-mass spectroscopy (UPLC-ESI-MS) analysis indicated the metabolites to be either sulfated- or phosphorylated- derivatives of aldrin-trans-diol, but with the metabolites retaining six chlorine atoms. Therefore, the candidate derivatives were synthesized and the retention times of the natural metabolite and the synthetic phosphate were compared. As a result of a co-injection experiment, the metabolites were determined to be aldrin-trans-diol exo- and endo-phosphates. These results were also supported by high-resolution-fast atom bombardment-mass spectrometry (HR-FAB-MS) of the natural metabolite (Δ = 0.63 ppm). Phosphorylation of aldrin-trans-diol is the first reported example of phosphate conjugation in microorganisms.