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Molecules 2012, 17(8), 9741-9753; doi:10.3390/molecules17089741

Fungal Strains as Catalysts for the Biotransformation of Halolactones by Hydrolytic Dehalogenation with the Dimethylcyclohexane System

Department of Chemistry, University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
Received: 26 June 2012 / Revised: 30 July 2012 / Accepted: 1 August 2012 / Published: 14 August 2012
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Abstract

Bicyclic chloro-, bromo- and iodo-γ-lactones with dimethylcyclohexane rings were used as substrates for bioconversion by several fungal strains (Fusarium, Botrytis and Beauveria). Most of the selected microorganisms transformed these lactones by hydrolytic dehalogenation into the new compound cis-2-hydroxy-4,6-dimethyl-9-oxabicyclo[4.3.0]- nonan-8-one, mainly the (−)-isomer. When iodo-γ-lactone was used as the substrate, two products were observed: a hydroxy-γ-lactone and an unsaturated lactone. The structures of all substrates and products were established on the basis of their spectral data. The mechanism of dehalogenation of three halolactones was also studied.
Keywords: lactones; biotransformation; hydrolytic dehalogenation; Fusarium species lactones; biotransformation; hydrolytic dehalogenation; Fusarium species
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MDPI and ACS Style

Grabarczyk, M. Fungal Strains as Catalysts for the Biotransformation of Halolactones by Hydrolytic Dehalogenation with the Dimethylcyclohexane System. Molecules 2012, 17, 9741-9753.

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