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. 1992 Apr;58(4):1360–1363. doi: 10.1128/aem.58.4.1360-1363.1992

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

M L Narro 1, C E Cerniglia 1, C Van Baalen 1, D T Gibson 1
PMCID: PMC195598  PMID: 1599253

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.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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