Evidence for an NIH shift in oxidation of naphthalene by the marine cyanobacterium Oscillatoria sp. strain JCM.
The marine cyanobacterium Oscillatoria sp. strain JCM oxidized naphthalene predominantly to 1-naphthol. Experiments with [1-2H]naphthalene and [2-2H]naphthalene indicated that 1-naphthol was formed with 68 and 74% retention of deuterium, respectively. No significant isotope effect was observed when the organism was incubated with a 1:1 mixture of naphthalene and [2H8]naphthalene. The results indicate that 1-naphthol is formed through a naphthalene 1,2-oxide intermediate, which rearranges spontaneously via an NIH shift mechanism.
Narro
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ML
Microbiology Division, National Center for Toxicological Research, Food and Drug Administration, Jefferson, Arkansas.
Cerniglia
C E
CE
Van Baalen
C
C
Gibson
D T
DT
D000458:Cyanobacteria / Q000378:metabolism*; D009281:Naphthalenes / Q000378:metabolism*; D010084:Oxidation-Reduction
D009281:Naphthalenes; C031721:naphthalene