Hydroxylation of bicyclic compounds by the o-xylene dioxygenase from Rhodococcus sp. strain DK17
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- Hydroxylation of bicyclic compounds by the o-xylene dioxygenase from Rhodococcus sp. strain DK17
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- Rhodococcus sp. strain DK17 유래 o-xylene dioxygenase에 의한 bicyclic compound의 hydroxylation 반응
- Yoo, Miyoun
Kang, Beom Sik
Zylstra, Gerben J.
- Rhodococcus; Site-directed mutagenesis; biphenyl; o-xylene dioxygenase; regioselective hydroxylation
- Issue Date
- Yoo, Miyoun, et al. 2011. Hydroxylation of bicyclic compounds by the o-xylene dioxygenase from Rhodococcus sp. strain DK17. 미국미생물학회. 미국미생물학회. 2011.05.21~.
- 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.
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