title: Evidence for an NIH shift in oxidation of naphthalene by the marine cyanobacterium Oscillatoria sp. strain JCM.
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.
authors.affiliation: Microbiology Division, National Center for Toxicological Research, Food and Drug Administration, Jefferson, Arkansas.
authors.forename: M L
authors.initials: ML
authors.lastname: Narro
authors.forename: C E
authors.initials: CE
authors.lastname: Cerniglia
authors.forename: C
authors.initials: C
authors.lastname: Van Baalen
authors.forename: D T
authors.initials: DT
authors.lastname: Gibson
mesh_terms: D000458:Cyanobacteria / Q000378:metabolism*; D009281:Naphthalenes / Q000378:metabolism*; D010084:Oxidation-Reduction
chemical_list: D009281:Naphthalenes; C031721:naphthalene