Dibenzothiophene Catabolism Proceeds via a Flavin-N5-oxide Intermediate

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• 作者：Sanjoy Adak ; Tadhg P. Begley
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：May 25, 2016
• 年：2016
• 卷：138
• 期：20
• 页码：6424-6426
• 全文大小：280K
• 年卷期：0
• ISSN：1520-5126

文摘

The dibenzothiophene catabolic pathway converts dibenzothiophene to 2-hydroxybiphenyl and sulfite. The third step of the pathway, involving the conversion of dibenzothiophene sulfone to 2-(2-hydroxyphenyl)-benzenesulfinic acid, is catalyzed by a unique flavoenzyme DszA. Mechanistic studies on this reaction suggest that the C2 hydroperoxide of dibenzothiophene sulfone reacts with flavin to form a flavin-N5-oxide. The intermediacy of the flavin-N5-oxide was confirmed by LC-MS analysis, a co-elution experiment with chemically synthesized FMN-N5-oxide and p>18p>O₂ labeling studies.