, Volume 8, Issue 5, pp 297–311 | Cite as

Ring cleavage of sulfur heterocycles: how does it happen?

  • David C. Bressler
  • Jason A. Norman
  • Phillip M. Fedorak


Sulfur heterocycles are common constituents ofpetroleum and liquids derived from coal, and they arefound in some secondary metabolites of microorganismsand plants. They exist primarily as saturated ringsand thiophenes. There are two major objectives drivinginvestigations of the microbial metabolism oforganosulfur compounds. One is the quest to develop aprocess for biodesulfurization of fossil fuels, andthe other is to understand the fates of organosulfurcompounds in petroleum- or creosote-contaminatedenvironments which is important in assessingbioremediation processes. For these processes to besuccessful, cleavage of different types of sulfurheterocyclic rings is paramount. This paper reviewsthe evidence for microbial ring cleavage of a varietyof organosulfur compounds and discusses the fewwell-studied cases which have shown that the C–S bondis most susceptible to breakage leading to disruptionof the ring. In most cases, the introduction of one ormore oxygen atom(s) onto the adjacent C atom and/oronto the S atom weakens the C–S bond, facilitating itscleavage. Although much is known about the thiophenering cleavage in dibenzothiophene, there is still agreat deal to be learned about the cleavage of othersulfur heterocycles.

benzothiophenes biodegradation biodesulfurization dibenzothiophenes thiacycloalkanes thiophenes 


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Copyright information

© Kluwer Academic Publishers 1997

Authors and Affiliations

  • David C. Bressler
    • 1
  • Jason A. Norman
    • 1
  • Phillip M. Fedorak
    • 1
  1. 1.Department of Biological ScienceUniversity of AlbertaEdmontonCanada

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