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

Ying Tao, William E. Bentley, Thomas Keith Wood

Research output: Contribution to journalArticle

21 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)614-621
Number of pages8
JournalApplied Microbiology and Biotechnology
Volume68
Issue number5
DOIs
StatePublished - Sep 1 2005

Fingerprint

Diethylhexyl Phthalate
Naphthol
Phenol
Phenols
Toluene
Naphthalene
Benzene
Pseudomonas mendocina
Naphthols
Solubility
Byproducts
Toxicity
Cells
2-naphthol
toluene-4-monooxygenase
Water
naphthalene

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Microbiology
  • Bioengineering
  • Microbiology (medical)

Cite this

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title = "Phenol and 2-naphthol production by toluene 4-monooxygenases using an aqueous/dioctyl phthalate system",
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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Phenol and 2-naphthol production by toluene 4-monooxygenases using an aqueous/dioctyl phthalate system. / Tao, Ying; Bentley, William E.; Wood, Thomas Keith.

In: Applied Microbiology and Biotechnology, Vol. 68, No. 5, 01.09.2005, p. 614-621.

Research output: Contribution to journalArticle

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