Catechols of novel substrates produced using the toluene ring oxidation pathway of Pseudomonas sp. strain T-12

Abstract

Pseudomonas sp. strain T-12 transforms several substituted benzenes to catechols utilizing the two initial enzymes of the toluene degradative pathway, toluene-2,3-dioxygenase and toluene-2,3-dihydrodiol dehydrogenase. Several novel substrates for this catechol synthesizing system have been previously identified including cyclopropylbenzene, β-methylstyrene, anisole, benzonitrile, α,α,α-trifluorotoluene, benzyl alcohol, 1-phenylethanol, 2-phenylethanol, p-difluorobenzene, and p-fluorobenzonitrile. The catechol products from these substrates are identified here as the 2,3-dihydroxy derivatives. Evidence is also presented which suggests that benzonitrile is metabolized like the halobenzenes and with 2,3-dihydroxybenzonitrile acting as a suicide substrate for catechol-2,3-dioxygenase. The scope and utility of Pseudomonas sp. strain T-12 catalyzed oxygenations is discussed.