Oxidation of naphthenoaromatic and methyl-substituted aromatic compounds by naphthalene 1,2-dioxygenase.

Applied and Environmental Microbiology
S A SelifonovP J Chapman

Abstract

Oxidation of acenaphthene, acenaphthylene, and fluorene was examined with recombinant strain Pseudomonas aeruginosa PAO1(pRE695) expressing naphthalene dioxygenase genes cloned from plasmid NAH7. Acenaphthene underwent monooxygenation to 1-acenaphthenol with subsequent conversion to 1-acenaphthenone and cis- and trans-acenaphthene-1,2-diols, while acenaphthylene was dioxygenated to give cis-acenaphthene-1,2-diol. Nonspecific dehydrogenase activities present in the host strain led to the conversion of both of the acenaphthene-1,2-diols to 1,2-acenaphthoquinone. The latter was oxidized spontaneously to naphthalene-1,8-dicarboxylic acid. No aromatic ring dioxygenation products were detected from acenaphthene and acenaphthylene. Mixed monooxygenase and dioxygenase actions of naphthalene dioxygenase on fluorene yielded products of benzylic 9-monooxygenation, aromatic ring dioxygenation, or both. The action of naphthalene dioxygenase on a variety of methyl-substituted aromatic compounds, including 1,2,4-trimethylbenzene and isomers of dimethylnaphthalene, resulted in the formation of benzylic alcohols, i.e., methyl group monooxygenation products, which were subsequently converted to the corresponding carboxylic acids by dehydrogenase...Continue Reading

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Citations

May 2, 2000·Applied and Environmental Microbiology·C Kazunga, M D Aitken
Dec 13, 2007·Applied Microbiology and Biotechnology·Zaira LópezMagdalena Grifoll
Nov 30, 2013·Letters in Applied Microbiology·S R Mueller-Spitz, K D Crawford
Dec 5, 2015·Frontiers in Microbiology·Jiri WaldOndrej Uhlik
Aug 12, 2009·Applied and Environmental Microbiology·Joaquim Vila, Magdalena Grifoll
May 9, 1998·Applied and Environmental Microbiology·T K DuttaI C Gunsalus
Dec 11, 2003·Microbiology and Molecular Biology Reviews : MMBR·Jonathan D Van HammeOwen P Ward
Sep 1, 2005·Applied Microbiology and Biotechnology·Zaira LópezMagdalena Grifoll
Sep 8, 2006·Applied and Environmental Microbiology·Siriwat PoonthrigpunPairoh Pinphanichakarn
Sep 22, 2007·Omics : a Journal of Integrative Biology·Prashant S PhaleRahul Shrivastava
Apr 5, 2017·The Science of the Total Environment·Lane G TidwellKim A Anderson
Aug 1, 1997·Applied and Environmental Microbiology·K G KroppP M Fedorak
Mar 1, 1997·Applied and Environmental Microbiology·M CasellasA M Solanas
Jul 21, 2017·Environmental Science & Technology·Jill E SchrlauLewis Semprini
May 16, 2001·Environmental Science & Technology·C KazungaR Sangaiah

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