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Appl Environ Microbiol. 1992 April; 58(4): 1360-1363

Evidence for an NIH shift in oxidation of naphthalene by the marine cyanobacterium Oscillatoria sp. strain JCM.

Microbiology Division, National Center for Toxicological Research, Food and Drug Administration, Jefferson, Arkansas.

ABSTRACT

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.