Effect of functional groups on the regioselectivity of a novel o-xylene dioxygenase from Rhodococcus sp. strain DK17

Dockyu Kim, Jong Suk Lee, Ki Young Choi, Young Soo Kim, Jung Nam Choi, Seong Ki Kim, Jong Chan Chae, Gerben J. Zylstra, Choong Hwan Lee, Eungbin Kim

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The o-xylene dioxygenase from Rhodococcus sp. strain DK17 possesses the ability to perform distinct regioselective hydroxylations depending on the position of the substituent groups on the aromatic ring. Bioconversion experiments were performed against the non-growth substrates p-xylene, biphenyl, and naphthalene, using induced cells of Escherichia coli BL21(DE3) harboring a recombinant expression plasmid of the DK17 o-xylene dioxygenase. Oxidation metabolites transformed from each substrate during the incubation were identified by a gas chromatography-mass spectrometry. p-Xylene was oxidized to cis-p-xylene dihydrodiol. Biphenyl and naphthalene were transformed into cis-2,3-biphenyl dihydrodiol and cis-1,2-naphthalene dihydrodiol, respectively. Considering that the DK17 o-xylene dioxygenase hydroxylates toluene and ethylbenzene at the 2,3 and the 3,4 positions on the aromatic ring in the ratios of 8:2 and 9:1, it is apparent that the size as well as the position of the substituent groups on the aromatic ring affect the regioselectivity of aromatic oxidation by this enzyme.

Original languageEnglish
Pages (from-to)221-225
Number of pages5
JournalEnzyme and Microbial Technology
Volume41
Issue number3
DOIs
Publication statusPublished - 2007 Aug 2

Fingerprint

Regioselectivity
Xylene
Functional groups
Naphthalene
Dioxygenases
Bioconversion
Oxidation
Hydroxylation
Substrates
Metabolites
Gas chromatography
Gas Chromatography-Mass Spectrometry
Escherichia coli
Mass spectrometry
Plasmids
Ethylbenzene
Enzymes
Toluene
diphenyl
Rhodococcus o-xylene dioxygenase

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Bioengineering
  • Biochemistry
  • Applied Microbiology and Biotechnology

Cite this

Kim, Dockyu ; Lee, Jong Suk ; Choi, Ki Young ; Kim, Young Soo ; Choi, Jung Nam ; Kim, Seong Ki ; Chae, Jong Chan ; Zylstra, Gerben J. ; Lee, Choong Hwan ; Kim, Eungbin. / Effect of functional groups on the regioselectivity of a novel o-xylene dioxygenase from Rhodococcus sp. strain DK17. In: Enzyme and Microbial Technology. 2007 ; Vol. 41, No. 3. pp. 221-225.
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Effect of functional groups on the regioselectivity of a novel o-xylene dioxygenase from Rhodococcus sp. strain DK17. / Kim, Dockyu; Lee, Jong Suk; Choi, Ki Young; Kim, Young Soo; Choi, Jung Nam; Kim, Seong Ki; Chae, Jong Chan; Zylstra, Gerben J.; Lee, Choong Hwan; Kim, Eungbin.

In: Enzyme and Microbial Technology, Vol. 41, No. 3, 02.08.2007, p. 221-225.

Research output: Contribution to journalArticle

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AB - The o-xylene dioxygenase from Rhodococcus sp. strain DK17 possesses the ability to perform distinct regioselective hydroxylations depending on the position of the substituent groups on the aromatic ring. Bioconversion experiments were performed against the non-growth substrates p-xylene, biphenyl, and naphthalene, using induced cells of Escherichia coli BL21(DE3) harboring a recombinant expression plasmid of the DK17 o-xylene dioxygenase. Oxidation metabolites transformed from each substrate during the incubation were identified by a gas chromatography-mass spectrometry. p-Xylene was oxidized to cis-p-xylene dihydrodiol. Biphenyl and naphthalene were transformed into cis-2,3-biphenyl dihydrodiol and cis-1,2-naphthalene dihydrodiol, respectively. Considering that the DK17 o-xylene dioxygenase hydroxylates toluene and ethylbenzene at the 2,3 and the 3,4 positions on the aromatic ring in the ratios of 8:2 and 9:1, it is apparent that the size as well as the position of the substituent groups on the aromatic ring affect the regioselectivity of aromatic oxidation by this enzyme.

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