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Multistep Conversion of para-Substituted Phenols by Phenol Hydroxylase and 2,3-Dihydroxybiphenyl 1,2-Dioxygenase

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Abstract

A multistep conversion system of para-substituted phenols by recombinant phenol hydroxylase (PHIND) and 2,3-dihydroxybiphenyl 1,2-dioxygenase (BphCLA-4) was constructed in this study. Docking studies with different para-substituted phenols and corresponding catechols inside of the active site of PHIND and BphCLA-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 PHIND 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 BphCLA-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.

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Acknowledgments

The authors gratefully acknowledge the financial supports from the National Natural Science Foundation of China (nos. 21176040 and 51078054).

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Authors and Affiliations

  1. Key Laboratory of Industrial Ecology and Environmental Engineering (Ministry of Education, China), School of Environmental Science and Technology, Dalian University of Technology, Dalian, 116024, China

    Yuanyuan Qu, Qiao Ma, Chunlei Kong, Hao Zhou, Xuwang Zhang & Jiti Zhou

  2. State Key Laboratory of Urban Water Resource and Environment, Harbin Institute of Technology, Harbin, 150090, China

    Shengnan Shi

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  1. Yuanyuan Qu
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  2. Shengnan Shi
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Correspondence to Yuanyuan Qu.

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Qu, Y., Shi, S., Ma, Q. et al. Multistep Conversion of para-Substituted Phenols by Phenol Hydroxylase and 2,3-Dihydroxybiphenyl 1,2-Dioxygenase. Appl Biochem Biotechnol 169, 2064–2075 (2013). https://doi.org/10.1007/s12010-013-0112-7

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