Evidence for an arene oxide-NIH shift pathway in the transformation of naphthalene to 1-naphthol byBacillus cereus

✍ Scribed by Carl E. Cerniglia; J. P. Freeman; Frederick E. Evans

• Book ID: 104762742
• Publisher: Springer
• Year: 1984
• Tongue: English
• Weight: 474 KB
• Volume: 138
• Category: Article
• ISSN: 0302-8933
• DOI: 10.1007/bf00410891

✦ Synopsis

Bacillus cereus ATCC 14579 transformed naphthalene predominately to l-naphthol. Experiments with [lgC]naphthalene showed that over a 24 h period, B. cereus oxidized 5.2% of the added naphthalene. 1-Naphthol accounted for approximately 80% of the total metabolites. B. cereus incubated with naphthalene under the presence of 1802 led to the isolation of 1-naphthol that contained 94% 1sO. The metabolism of [1-2H] -and [2-2H]-naphthalene by B. cereus yielded 1-naphthol which retained 95% and 94% deuterium, respectively, as determined by mass spectral analysis. NMR spectroscopic analysis of the deuterated l-naphthol formed from [1-2H]-naphthalene indicated an NIH shift mechanism in which 19% of the deuterium migrated from the C-1 to the C-2 position. The 180 2 and NIH shift experiments implicate naphthalene-l,2-oxide as an intermediate in the formation of 1-naphthol from naphthalene by B. cereus.