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National Institute of Environmental Health Sciences

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Publication Detail

Title: Differential degradation of bicyclics with aromatic and alicyclic rings by Rhodococcus sp. strain DK17.

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

Published In Appl Environ Microbiol, (2011 Dec)

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.

PubMed ID: 21965391 Exiting the NIEHS site

MeSH Terms: Bridged Bicyclo Compounds, Heterocyclic/metabolism*; Cloning, Molecular; Escherichia coli/genetics; Escherichia coli/metabolism; Gas Chromatography-Mass Spectrometry; Gene Expression; Hydrocarbons, Alicyclic/metabolism*; Magnetic Resonance Spectroscopy; Polycyclic Aromatic Hydrocarbons/metabolism*; Rhodococcus/chemistry; Rhodococcus/enzymology; Rhodococcus/genetics; Rhodococcus/metabolism*

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