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Benzylic and aryl hydroxylations of m-xylene by o-xylene dioxygenase from Rhodococcus sp. strain DK17

Cited 8 time in scopus
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Title
Benzylic and aryl hydroxylations of m-xylene by o-xylene dioxygenase from Rhodococcus sp. strain DK17
Other Titles
Rhodococcus sp. strain DK17이 생산하는 o-xylene dioxygenase에 의한 m-xylene의 benzylic- 및 aryl-hydroxylation 반응
Authors
Kim, Dockyu
Jung Nam Choi
Zylstra, Gerben J.
Kim, Eungbin
Kang, Beom Sik
Choong Hwan Lee
Yoo, Miyoun
Ki Young Choi
Subject
Biotechnology & Applied Microbiology
Keywords
Benzylic hydroxylation; Rhodococcus; meta Effect; o-Xylene dioxygenase
Issue Date
2010
Publisher
Springer Berlin / Heidelberg
Citation
Kim, Dockyu, et al. 2010. "Benzylic and aryl hydroxylations of m-xylene by o-xylene dioxygenase from Rhodococcus sp. strain DK17". APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 86(6): 1841-1847.
Abstract
Escherichia coli cells expressing Rhodococcus DK17 o-xylene dioxygenase genes were used for bioconversion of m-xylene. Gas chromatography-mass spectrometry analysis of the oxidation products detected 3 methylbenzylalcohol and 2,4-dimethylphenol in the ratio 9:1. Molecular modeling suggests that o-xylene dioxygenase can hold xylene isomers at a kink region between α6 and α7 helices of the active site and α9 helix covers the substrates. m-Xylene is unlikely to locate at the active site with a methyl group facing the kink region because this configuration would not fit within the substrate-binding pocket. The m-xylene molecule can flip horizontally to expose the meta-position methyl group to the catalytic motif. In this configuration, 3 methylbenzylalcohol could be formed, presumably due to the meta effect. Alternatively, the m-xylene molecule can rotate counterclockwise, allowing the catalytic motif to hydroxylate at C-4 yielding 2,4-dimethylphenol. Site-directed mutagenesis combined with structural and functional analyses suggests that the alanine-218 and the aspartic acid-262 in the α7 and the α9 helices play an important role in positioning m-xylene, respectively
URI
http://repository.kopri.re.kr/handle/201206/6135
DOI
http://dx.doi.org/10.1007/s00253-009-2418-5
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