Stereochemistry and evidence for an arene oxide-NIH shift pathway in the fungal metabolism of naphthalene

Chemico-biological Interactions
C E CernigliaS K Yang

Abstract

The mechanism of naphthalene oxidation by the filamentous fungus, Cunninghamella elegans is described. C. elegans oxidized naphthalene predominately to trans-1,2-dihydroxy-1,2-dihydroxy-1,2-dihydronaphthalene. A trans configuration was assigned for the dihydrodiol by nuclear magnetic resonance (NMR) spectroscopy at 500 MHz which showed a large coupling constant (J1,2) of 11.0 Hz. Comparison of the circular dichroism spectrum of the fungal trans-1,2-dihydroxy-1,2-dihydronaphthalene to that formed by mammalian enzyme systems indicated that the fungal dihydrodiol contained 76% (+)-(1S,2S)-dihydrodiol as the predominant enantiomer. Other naphthalene metabolites formed by C. elegans were identified as 1-naphthol, 2-naphthol and 4-hydroxy-1-tetralone. Incubation of C. elegans with naphthalene and 18O2 indicated that the trans-1,2-dihydroxy-1,2-dihydronaphthalene contained one atom of molecular oxygen which indicated a monooxygenase catalyzed reaction while similar incubations with naphthalene and H182O indicated that the other oxygen atom in trans-1,2-dihydroxy-1,2-dihydronaphthalene was derived from water. Mass spectral analysis of the acid-catalyzed dehydration products of the dihydrodiol indicated that the naphthalene dihydrodiol ...Continue Reading

References

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Citations

Jan 1, 1992·Journal of Industrial Microbiology·J B Sutherland
Jan 1, 1986·Journal of Toxicology and Environmental Health·G C MillnerC E Cerniglia
Oct 1, 1990·The Journal of Applied Bacteriology·A H Neilson
Oct 19, 2002·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Joanna D MoodyCarl E Cerniglia
Aug 4, 1998·Applied and Environmental Microbiology·J V PothuluriC E Cerniglia
Aug 1, 1984·Applied and Environmental Microbiology·C E CernigliaJ P Freeman
Jan 1, 1984·Applied and Environmental Microbiology·C E Cerniglia, S K Yang
Sep 1, 1989·Applied and Environmental Microbiology·C E CernigliaF E Evans
Nov 1, 1992·Applied and Environmental Microbiology·J V PothuluriC E Cerniglia
Jun 1, 1993·Applied and Environmental Microbiology·J V PothuluriC E Cerniglia
Mar 1, 1990·Applied and Environmental Microbiology·C E CernigliaF E Evans
Jan 1, 1997·Applied and Environmental Microbiology·C BoydK Wilson

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