Conversion of 2-fluoromuconate to cis-dienelactone by purified enzymes from Rhodococcus opacus 1cp

I.P. Solyanikova, O.V. Moisseeva, S. Boeren, M.G. Boersma, M.P. Kolomytseva, J.J.M. Vervoort, I.M.C.M. Rietjens, L.A. Golovleva, W.J.H. van Berkel

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8 Citations (Scopus)

Abstract

The present study describes the 19F nuclear magnetic resonance analysis of the conversion of 3-halocatechols to lactones by purified chlorocatechol 1,2-dioxygenase (ClcA2), chloromuconate cycloisomerase (ClcB2), and chloromuconolactone dehalogenase (ClcF) from Rhodococcus opacus 1cp grown on 2-chlorophenol. The 3-halocatechol substrates were produced from the corresponding 2-halophenols by either phenol hydroxylase from Trichosporon cutaneum or 2-hydroxybiphenyl 3-mono-oxygenase from Pseudomonas azelaica. Several fluoromuconates resulting from intradiol ring cleavage by ClcA2 were identified. ClcB2 converted 2-fluoromuconate to 5-fluoromuconolactone and 2-chloro-4-fluoromuconate to 2-chloro-4-fluoromuconolactone. Especially the cycloisomerization of 2-fluoromuconate is a new observation. ClcF catalyzed the dehalogenation of 5-fluoromuconolactone to cis-dienelactone. The ClcB2 and ClcF-mediated reactions are in line with the recent finding of a second cluster of chlorocatechol catabolic genes in R. opacus 1cp which provides a new route for the microbial dehalogenation of 3-chlorocatechol
Original languageEnglish
Pages (from-to)5636-5642
JournalApplied and Environmental Microbiology
Volume69
Issue number9
DOIs
Publication statusPublished - 2003

Keywords

  • halogenated aromatic-compounds
  • alcaligenes-eutrophus jmp-134
  • pseudomonas-azelaica hbp1
  • modified ortho-pathway
  • phenol hydroxylase
  • chemical-structure
  • erythropolis 1cp
  • 2-hydroxybiphenyl 3-monooxygenase
  • chloromuconate cycloisomerases
  • chlorocatechol 1

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