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Appl Environ Microbiol. 1994 October; 60(10): 3624-3631
Copyright © 1994, American Society for Microbiology. All Rights Reserved.

Microbially Mediated Formation of Benzonaphthothiophenes from Benzo[b]thiophenes

Kevin G. Kropp1, José A. Gonçalves1,{dagger}, Jan T. Andersson2 and Phillip M. Fedorak1,*

1 Department of Biological Sciences, University of Alberta, Edmonton, Alberta, Canada T6G 2E9
2 Department of Analytical Chemistry, University of Münster, D-48149 Münster, Germany

ABSTRACT

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 H2O2.

FOOTNOTES

* Corresponding author. Phone: (403) 492-3670. Fax: (403) 492-9234.

{dagger} Present address: EAG/2 INTEVEP, S.A.2, Los Teques Edo. Miranda Apartado 76343, Caracas 1070A, Venezuela.

Appl Environ Microbiol. 1994 October; 60(10): 3624-3631
Copyright © 1994, American Society for Microbiology. All Rights Reserved.



This article has been cited by other articles:

  • Gai, Z., Yu, B., Wang, X., Deng, Z., Xu, P. (2008). Microbial transformation of benzothiophenes, with carbazole as the auxiliary substrate, by Sphingomonas sp. strain XLDN2-5. Microbiology 154: 3804-3812 [Abstract] [Full Text]  
  • Bressler, D. C., Fedorak, P. M. (2001). Identification of Disulfides from the Biodegradation of Dibenzothiophene. Appl. Environ. Microbiol. 67: 5084-5093 [Abstract] [Full Text]  
  • Bressler, D. C., Fedorak, P. M. (2001). Purification, Stability, and Mineralization of 3-Hydroxy-2- Formylbenzothiophene, a Metabolite of Dibenzothiophene. Appl. Environ. Microbiol. 67: 821-826 [Abstract] [Full Text]  


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