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Biotransformation of Chloro-Substituted Indoles to Indigoids by Phenol Hydroxylase from Arthrobacter sp. W1

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Abstract

Recombinant Escherichia coli cells expressing phenol hydroxylase (designated as strain PHIND) were used to synthesize chloro-substituted indigoids by the transformation of indoles. The optimal conditions for the biotransformation of 4- and 7-chloroindole were determined by response surface methodology. Biotransformation kinetic assays revealed that strain PHIND showed high catalytic efficiency for 4- and 7-chloroindole. The formation rate of 7,7′-dichloroindigo (1.35 unit/mg cell dry weight) by strain PHIND was 1.14-fold higher than that of 4,4′-dichloroindigo. The intermediates of 7-chloroindole biotransformation were identified by high-performance liquid chromatography–mass spectroscopy, and the biotransformation mechanism was also proposed. These results suggested that there was a potential application of strain PHIND in the biotransformation of chloro-substituted indoles to valuable indigoids.

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Acknowledgments

This work was supported by the National Creative Research Group from the National Natural Science Foundation of China (no. 51121062), the National Natural Science Foundation of China (nos. 51108120, 51078054, and 51178139), and the 4th Special Financial Grant from the China Postdoctoral Science Foundation (no. 201104430).

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Authors and Affiliations

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

    Shengnan Shi, Fang Ma, Tieheng Sun & Ang Li

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

    Jiti Zhou & Yuanyuan Qu

Authors
  1. Shengnan Shi
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  2. Fang Ma
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  3. Tieheng Sun
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  4. Ang Li
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  5. Jiti Zhou
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Correspondence to Fang Ma or Yuanyuan Qu.

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Shi, S., Ma, F., Sun, T. et al. Biotransformation of Chloro-Substituted Indoles to Indigoids by Phenol Hydroxylase from Arthrobacter sp. W1. Appl Biochem Biotechnol 170, 951–961 (2013). https://doi.org/10.1007/s12010-013-0234-y

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  • DOI: https://doi.org/10.1007/s12010-013-0234-y

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