Differential degradation of bicyclics with aromatic and alicyclic rings by rhodococcus sp. Strain DK17

Dockyu Kim, Miyoun Yoo, Ki Young Choi, Beom Sik Kang, Tai Kyoung Kim, Soon Gyu Hong, Gerben J. Zylstra, Eungbin Kim

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The metabolically versatile Rhodococcus sp. strain DK17 is able to grow on tetralin and indan but cannot use their respective desaturated counterparts, 1,2-dihydronaphthalene and indene, as sole carbon and energy sources. Metabolite analyses by gas chromatography-mass spectrometry and nuclear magnetic resonance spectrometry clearly show that (i) the meta-cleavage dioxygenase mutant strain DK180 accumulates 5,6,7,8-tetrahydro-1,2-naphthalene diol, 1,2-indene diol, and 3,4-dihydro-naphthalene-1,2-diol from tetralin, indene, and 1,2-dihydronaphthalene, respectively, and (ii) when expressed in Escherichia coli, the DK17 o-xylene dioxygenase transforms tetralin, indene, and 1,2-dihydronaphthalene into tetralin cis-dihydrodiol, indan-1,2-diol, and cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene, respectively. Tetralin, which is activated by aromatic hydroxylation, is degraded successfully via the ring cleavage pathway to support growth of DK17. Indene and 1,2-dihydronaphthalene do not serve as growth substrates because DK17 hydroxylates them on the alicyclic ring and further metabolism results in a dead-end metabolite. This study reveals that aromatic hydroxylation is a prerequisite for proper degradation of bicyclics with aromatic and alicyclic rings by DK17 and confirms the unique ability of the DK17 o-xylene dioxygenase to perform distinct regioselective hydroxylations.

Original languageEnglish
Pages (from-to)8280-8287
Number of pages8
JournalApplied and Environmental Microbiology
Volume77
Issue number23
DOIs
Publication statusPublished - 2011 Dec 1

Fingerprint

Rhodococcus
xylene
naphthalene
glycols
cleavage
aromatic compounds
metabolite
Dioxygenases
hydroxylation
Hydroxylation
degradation
spectrometry
nuclear magnetic resonance
gas chromatography
transform
mass spectrometry
metabolism
substrate
carbon
metabolites

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Food Science
  • Applied Microbiology and Biotechnology
  • Ecology

Cite this

Kim, Dockyu ; Yoo, Miyoun ; Choi, Ki Young ; Kang, Beom Sik ; Kim, Tai Kyoung ; Hong, Soon Gyu ; Zylstra, Gerben J. ; Kim, Eungbin. / Differential degradation of bicyclics with aromatic and alicyclic rings by rhodococcus sp. Strain DK17. In: Applied and Environmental Microbiology. 2011 ; Vol. 77, No. 23. pp. 8280-8287.
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abstract = "The metabolically versatile Rhodococcus sp. strain DK17 is able to grow on tetralin and indan but cannot use their respective desaturated counterparts, 1,2-dihydronaphthalene and indene, as sole carbon and energy sources. Metabolite analyses by gas chromatography-mass spectrometry and nuclear magnetic resonance spectrometry clearly show that (i) the meta-cleavage dioxygenase mutant strain DK180 accumulates 5,6,7,8-tetrahydro-1,2-naphthalene diol, 1,2-indene diol, and 3,4-dihydro-naphthalene-1,2-diol from tetralin, indene, and 1,2-dihydronaphthalene, respectively, and (ii) when expressed in Escherichia coli, the DK17 o-xylene dioxygenase transforms tetralin, indene, and 1,2-dihydronaphthalene into tetralin cis-dihydrodiol, indan-1,2-diol, and cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene, respectively. Tetralin, which is activated by aromatic hydroxylation, is degraded successfully via the ring cleavage pathway to support growth of DK17. Indene and 1,2-dihydronaphthalene do not serve as growth substrates because DK17 hydroxylates them on the alicyclic ring and further metabolism results in a dead-end metabolite. This study reveals that aromatic hydroxylation is a prerequisite for proper degradation of bicyclics with aromatic and alicyclic rings by DK17 and confirms the unique ability of the DK17 o-xylene dioxygenase to perform distinct regioselective hydroxylations.",
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Differential degradation of bicyclics with aromatic and alicyclic rings by rhodococcus sp. Strain DK17. / Kim, Dockyu; Yoo, Miyoun; Choi, Ki Young; Kang, Beom Sik; Kim, Tai Kyoung; Hong, Soon Gyu; Zylstra, Gerben J.; Kim, Eungbin.

In: Applied and Environmental Microbiology, Vol. 77, No. 23, 01.12.2011, p. 8280-8287.

Research output: Contribution to journalArticle

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AU - Kim, Dockyu

AU - Yoo, Miyoun

AU - Choi, Ki Young

AU - Kang, Beom Sik

AU - Kim, Tai Kyoung

AU - Hong, Soon Gyu

AU - Zylstra, Gerben J.

AU - Kim, Eungbin

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AB - The metabolically versatile Rhodococcus sp. strain DK17 is able to grow on tetralin and indan but cannot use their respective desaturated counterparts, 1,2-dihydronaphthalene and indene, as sole carbon and energy sources. Metabolite analyses by gas chromatography-mass spectrometry and nuclear magnetic resonance spectrometry clearly show that (i) the meta-cleavage dioxygenase mutant strain DK180 accumulates 5,6,7,8-tetrahydro-1,2-naphthalene diol, 1,2-indene diol, and 3,4-dihydro-naphthalene-1,2-diol from tetralin, indene, and 1,2-dihydronaphthalene, respectively, and (ii) when expressed in Escherichia coli, the DK17 o-xylene dioxygenase transforms tetralin, indene, and 1,2-dihydronaphthalene into tetralin cis-dihydrodiol, indan-1,2-diol, and cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene, respectively. Tetralin, which is activated by aromatic hydroxylation, is degraded successfully via the ring cleavage pathway to support growth of DK17. Indene and 1,2-dihydronaphthalene do not serve as growth substrates because DK17 hydroxylates them on the alicyclic ring and further metabolism results in a dead-end metabolite. This study reveals that aromatic hydroxylation is a prerequisite for proper degradation of bicyclics with aromatic and alicyclic rings by DK17 and confirms the unique ability of the DK17 o-xylene dioxygenase to perform distinct regioselective hydroxylations.

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