Cerniglia C E, Freeman J P, Evans F E
Arch Microbiol. 1984 Aug;138(4):283-6. doi: 10.1007/BF00410891.
Bacillus cereus ATCC 14579 transformed naphthalene predominately to 1-naphthol. Experiments with [14C]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 18O2 led to the isolation of 1-naphthol that contained 94% 18O. 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 1-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 18O2 and NIH shift experiments implicate naphthalene-1,2-oxide as an intermediate in the formation of 1-naphthol from naphthalene by B. cereus.
蜡样芽孢杆菌ATCC 14579将萘主要转化为1-萘酚。用[14C]萘进行的实验表明，在24小时内，蜡样芽孢杆菌氧化了5.2%的添加萘。1-萘酚约占总代谢产物的80%。在18O2存在下，蜡样芽孢杆菌与萘一起培养，得到了含94% 18O的1-萘酚。蜡样芽孢杆菌对[1-2H]-和[2-2H]-萘的代谢产物1-萘酚，经质谱分析测定，分别保留了95%和94%的氘。对由[1-2H]-萘形成的氘代1-萘酚进行核磁共振光谱分析，表明存在NIH迁移机制，其中19%的氘从C-1迁移到了C-2位置。18O2实验和NIH迁移实验表明，萘-1,2-氧化物是蜡样芽孢杆菌将萘转化为1-萘酚过程中的一个中间体。
