Ring cleavage of sulfur heterocycles: how does it happen?

被引:34
作者
Bressler, DC [1 ]
Norman, JA [1 ]
Fedorak, PM [1 ]
机构
[1] Univ Alberta, Dept Biol Sci, Edmonton, AB T6G 2E9, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
benzothiophenes; biodegradation; biodesulfurization; dibenzothiophenes; thiacycloalkanes; thiophenes;
D O I
10.1023/A:1008283207090
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Sulfur heterocycles are common constituents of petroleum and liquids derived from coal, and they are found in some secondary metabolites of microorganisms and plants. They exist primarily as saturated rings and thiophenes. There are two major objectives driving investigations of the microbial metabolism of organosulfur compounds. One is the quest to develop a process for biodesulfurization of fossil fuels, and the other is to understand the fates of organosulfur compounds in petroleum-or creosote-contaminated environments which is important in assessing bioremediation processes. For these processes to be successful, cleavage of different types of sulfur heterocyclic rings is paramount. This paper reviews the evidence for microbial ring cleavage of a variety of organosulfur compounds and discusses the few well-studied cases which have shown that the C-S bond is most susceptible to breakage leading to disruption of the ring. In most cases, the introduction of one or more oxygen atom(s) onto the adjacent C atom and/or onto the S atom weakens the C-S bond, facilitating its cleavage. Although much is known about the thiophene ring cleavage in dibenzothiophene. there is still a great deal to be learned about the cleavage of other sulfur heterocycles.
引用
收藏
页码:297 / 311
页数:15
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