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

doi:10.1128/AEM.69.9.5636-5642.2003

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

Research output: Contribution to journal › Article › Academic › peer-review

15 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 language	English
Pages (from-to)	5636-5642
Journal	Applied and Environmental Microbiology
Volume	69
Issue number	9
DOIs	https://doi.org/10.1128/AEM.69.9.5636-5642.2003
Publication status	Published - 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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10.1128/AEM.69.9.5636-5642.2003

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Solyanikova, I. P., Moisseeva, O. V., Boeren, S., Boersma, M. G., Kolomytseva, M. P., Vervoort, J. J. M., Rietjens, I. M. C. M., Golovleva, L. A., & van Berkel, W. J. H. (2003). Conversion of 2-fluoromuconate to cis-dienelactone by purified enzymes from Rhodococcus opacus 1cp. Applied and Environmental Microbiology, 69(9), 5636-5642. https://doi.org/10.1128/AEM.69.9.5636-5642.2003

@article{a302b279e23b486480451cfb418cdbfa,

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

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",

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",

author = "I.P. Solyanikova and O.V. Moisseeva and S. Boeren and M.G. Boersma and M.P. Kolomytseva and J.J.M. Vervoort and I.M.C.M. Rietjens and L.A. Golovleva and \{van Berkel\}, W.J.H.",

year = "2003",

doi = "10.1128/AEM.69.9.5636-5642.2003",

language = "English",

volume = "69",

pages = "5636--5642",

journal = "Applied and Environmental Microbiology",

issn = "0099-2240",

publisher = "American Society for Microbiology",

number = "9",

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TY - JOUR

T1 - Conversion of 2-fluoromuconate to cis-dienelactone by purified enzymes from Rhodococcus opacus 1cp

AU - Solyanikova, I.P.

AU - Moisseeva, O.V.

AU - Boeren, S.

AU - Boersma, M.G.

AU - Kolomytseva, M.P.

AU - Vervoort, J.J.M.

AU - Rietjens, I.M.C.M.

AU - Golovleva, L.A.

AU - van Berkel, W.J.H.

PY - 2003

Y1 - 2003

N2 - 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

AB - 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

KW - halogenated aromatic-compounds

KW - alcaligenes-eutrophus jmp-134

KW - pseudomonas-azelaica hbp1

KW - modified ortho-pathway

KW - phenol hydroxylase

KW - chemical-structure

KW - erythropolis 1cp

KW - 2-hydroxybiphenyl 3-monooxygenase

KW - chloromuconate cycloisomerases

KW - chlorocatechol 1

U2 - 10.1128/AEM.69.9.5636-5642.2003

DO - 10.1128/AEM.69.9.5636-5642.2003

M3 - Article

SN - 0099-2240

VL - 69

SP - 5636

EP - 5642

JO - Applied and Environmental Microbiology

JF - Applied and Environmental Microbiology

IS - 9

ER -

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

Abstract

Keywords

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