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Hydroxylation of bicyclic compounds by the o-xylene dioxygenase from Rhodococcus sp. strain DK17

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Title
Hydroxylation of bicyclic compounds by the o-xylene dioxygenase from Rhodococcus sp. strain DK17
Other Titles
Rhodococcus sp. strain DK17 유래 o-xylene dioxygenase에 의한 bicyclic compound의 hydroxylation 반응
Authors
Yoo, Miyoun
Kim, Dockyu
Kim, Eungbin
Kang, Beom Sik
Zylstra, Gerben J.
Keywords
Rhodococcus; Site-directed mutagenesis; biphenyl; o-xylene dioxygenase; regioselective hydroxylation
Issue Date
2011
Citation
Yoo, Miyoun, et al. 2011. Hydroxylation of bicyclic compounds by the o-xylene dioxygenase from Rhodococcus sp. strain DK17. 미국미생물학회. 미국미생물학회. 2011.05.21~.
Abstract
Rhodococcus sp. strain DK17 can metabolize various benzene derivatives including BTEX and bicyclic compounds through a common pathway initiated by o-xylene dioxygenase. The DK17 o-xylene dioxygenase enzyme possesses the unique ability to perform distinct regioselective hydroxylations that depend on the position and the size of the substituent groups on the aromatic ring. Bioconversion experiments were performed to further investigate the ability of the DK17 o-xylene dioxygenases to hydroxylate bulkier substrates including 1,2-dihydronaphthalene and biphenyl using the wild-type and mutant enzymes. Hydroxylation metabolites were identified and quantified by gas chromatography- mass spectrometry. The DK17 o-xylene dioxygenase hydroxylates 1,2-dihydronaphthalene at the 1,2 position of the alicyclic moiety to form cis-1,2-dihydroxy-1,2,3,4- tetrahydronaphthalene. Interestingly, one mutant enzyme (L266F) produced much more 2- hydroxybiphenyl (2.43 vs. 0.1 μg/L) and 3-hydroxybiphenyl (1.97 vs. 0.03 μg/L) than the wild-type. Site-directed mutagenesis combined with structural and functional analyses indicates that hydrophobic interactions and shielding effects against water are important factors in the hydroxylation of biphenyl by the o-xylene dioxygenase. In particular, the residue at position 266 plays a key role in coordinating the reaction.
URI
http://repository.kopri.re.kr/handle/201206/8503
Conference Name
미국미생물학회
Conference Place
미국미생물학회
Conference Date
2011.05.21~
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