Evidence for an NIH shift in oxidation of naphthalene by the marine cyanobacterium Oscillatoria sp. strain JCM
Autor: | C Van Baalen, Carl E. Cerniglia, D T Gibson, M L Narro |
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Rok vydání: | 1992 |
Předmět: |
Cyanobacteria
Oscillatoria Ecology biology Strain (chemistry) Stereochemistry Epoxide Naphthalenes Phenanthrene Metabolic intermediate Photochemistry biology.organism_classification Applied Microbiology and Biotechnology chemistry.chemical_compound chemistry NIH shift Oxidation-Reduction Research Article Food Science Biotechnology Naphthalene |
Zdroj: | Applied and Environmental Microbiology. 58:1360-1363 |
ISSN: | 1098-5336 0099-2240 |
DOI: | 10.1128/aem.58.4.1360-1363.1992 |
Popis: | 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. |
Databáze: | OpenAIRE |
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