A multistep conversion system of para-substituted phenols by recombinant phenol hydroxylase (PH(IND)) and 2,3-dihydroxybiphenyl 1,2-dioxygenase (BphC(LA-4)) was constructed in this study. Docking studies with different para-substituted phenols and corresponding catechols inside of the active site of PH(IND) and BphC(LA-4) predicted that all the substrates should be transformed. High-performance liquid chromatography-mass spectrometry analysis showed that the products of multistep conversion were the corresponding para-substituted catechols and semialdehydes. For the first-step conversion, the formation rate of 4-fluorocatechol (0.39 μM/min/mg dry weight) by strain PH(IND) hydroxylation was 1.15, 6.50, 3.00, and 1.18-fold higher than the formation of 4-chlorocatechol, 4-bromocatechol, 4-nitrocatechol, and 4-methylcatechol, respectively. For the second-step conversion, the formation rates of semialdehydes by strain BphC(LA-4) were as follows: 5-fluoro-HODA>5-chloro-HODA>2-hydroxy-5-nitro-ODA>5-bromo-HODA>2-hydroxy-5-methyl-ODA. The present study suggested that the multistep conversion by both ring hydroxylase and cleavage dioxygenase should be potential in the synthesis of industrial precursors and provide a novel avenue in the wastewater recycling treatment.

译文

通过重组酚羟化酶 (PH(IND)) 和2,3-二羟基联苯1,2-双加氧酶 (BphC(LA-4)) 构建了对位取代酚的多步转化系统。与PH(IND) 和BphC(LA-4) 活性位点内的不同对位取代酚和相应的儿茶酚的对接研究预测,所有底物都应转化。高效液相色谱-质谱分析表明,多步转化的产物是相应的对位取代的儿茶酚和半醛。对于第一步转化,菌株PH(IND) 羟基化作用下4-氟邻苯二酚 (0.39 μ m/min/mg干重) 的形成速率比4-氯邻苯二酚、4-溴邻苯二酚、4-硝基邻苯二酚和4-甲基邻苯二酚的形成速率分别高1.15、6.50、3.00和1.18倍。对于第二步转化,菌株BphC(LA-4) 的半醛形成速率如下: 5-氟-hoda> 5-氯-hoda> 2-羟基-5-硝基-oda> 5-溴-hoda> 2-羟基-5-甲基-oda。本研究表明,环羟化酶和裂解双加氧酶的多步转化在工业前体的合成中应具有潜力,并为废水回收处理提供了新的途径。

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