Department of Biological Sciences, University of Alberta, Edmonton, Alberta, Canada T6G 2E9.
Appl Environ Microbiol. 1994 Oct;60(10):3624-31. doi: 10.1128/aem.60.10.3624-3631.1994.
Studies of the microbial metabolism of benzo[b]thiophene (molecular weight 134) by three Pseudomonas isolates showed the formation of benzothiophene sulfoxide, benzothiophene sulfone, and a sulfur-containing metabolite with a molecular weight of 234. Desulfurization of the high-molecular-weight product with nickel boride gave 1-phenylnaphthalene, indicating that the metabolite was benzo[b]naphtho[1,2-d]thiophene. Similarly, the isolates were capable of producing the analogous dimethyl-substituted benzonaphthothiophenes from methylbenzothiophenes that had the methyl substitution on the benzene ring. The formation of benzo[b] naphtho[1,2-d]thiophene was also observed when a petroleum-degrading mixed culture was incubated with benzothiophene-supplemented Prudhoe Bay crude oil. Investigations into the mechanism of formation of these high-molecular-weight compounds showed that they resulted from an abiotic, Diels-Alder-type condensation of two molecules of the sulfoxide, which were microbially produced from the respective benzothiophene, with the subsequent loss of two atoms of hydrogen and oxygen and one atom of sulfur. The condensation products also formed from the sulfoxides of benzothiophene and methylbenzothiophenes when the sulfoxides were enzymatically synthesized by oxidation of the benzothiophene with horse heart cytochrome c and H(2)O(2).
研究三种假单胞菌属分离物对苯并[b]噻吩（分子量 134）的微生物代谢，发现形成了苯并噻吩砜、苯并噻吩二砜和一种分子量为 234 的含硫代谢产物。用硼化镍对高分子量产物进行脱硫，得到 1-苯基萘，表明代谢产物为苯并[b]萘并[1,2-d]噻吩。同样，这些分离物能够从苯环上有甲基取代的甲基苯并噻吩中产生类似的二甲基取代苯并萘并噻吩。当用补充有苯并噻吩的普拉德霍湾原油培养石油降解混合培养物时，也观察到苯并[b]萘并[1,2-d]噻吩的形成。对这些高分子量化合物形成机制的研究表明，它们是由两种微生物产生的亚砜分子的非生物、Diels-Alder 型缩合形成的，亚砜分别由相应的苯并噻吩产生，随后失去两个氢原子、两个氧原子和一个硫原子。当用马心细胞色素 c 和 H(2)O(2)氧化苯并噻吩酶促合成亚砜时，这些缩合产物也可以从苯并噻吩和甲基苯并噻吩的亚砜中形成。
