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Phenol and 2-naphthol production by toluene 4-monooxygenases using an aqueous/dioctyl phthalate system

  • Biotechnological Products and Process Engineering
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Abstract

A two-phase system is developed here for converting: (1) benzene to phenol and (2) naphthalene to 2-naphthol, using whole cells expressing wild-type toluene 4-monooxygenase (T4MO) and the alpha subunit variant TmoA I100A from Pseudomonas mendocina KR1. Using the T4MO TmoA I100A variant, the solubility of naphthalene was enhanced and the toxicity of the naphthols was prevented by the use of a water/dioctyl phthalate (80:20, vol%) system which yielded 21-fold more 2-naphthol. More than 99% 2-naphthol was extracted to the dioctyl phthalate phase, dihydroxynaphthalene formation was prevented, 92% 2-naphthol was formed, and 12% naphthalene was converted. Similarly, using 50 vol% dioctyl phthalate, an initial concentration of 3.0 g l−1 (39 mM), and wild-type T4MO, a 51±9% conversion of benzene was obtained and phenol was produced at a purity of 97%. Relative to the one-phase system, there was a 12-fold reduction in the formation of the byproduct catechol.

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Acknowledgements

This research was supported by the National Science Foundation (BES-0124401) and the United States Environmental Protection Agency.

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Authors and Affiliations

  1. Departments of Chemical Engineering & Molecular and Cell Biology, University of Connecticut, Storrs, CT 06269-3222, USA

    Ying Tao & Thomas K. Wood

  2. Department of Chemical Engineering, University of Maryland, College Park, MD 20742, USA

    William E. Bentley

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  1. Ying Tao
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  2. William E. Bentley
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  3. Thomas K. Wood
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Correspondence to Thomas K. Wood.

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Tao, Y., Bentley, W.E. & Wood, T.K. Phenol and 2-naphthol production by toluene 4-monooxygenases using an aqueous/dioctyl phthalate system. Appl Microbiol Biotechnol 68, 614–621 (2005). https://doi.org/10.1007/s00253-005-1939-9

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  • DOI: https://doi.org/10.1007/s00253-005-1939-9

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