Dibenzothiophene Catabolism Proceeds via a Flavin-N5-oxide Intermediate

Dibenzothiophene Catabolism Proceeds via a Flavin-N5-oxide Intermediate

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 r...

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Veröffentlicht in:Journal of the American Chemical Society 2016-05, Vol.138 (20), p.6424-6426
Hauptverfasser: Adak, Sanjoy, Begley, Tadhg P
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Chromatography, Liquid
Flavins - metabolism
liquid chromatography
Mass Spectrometry
metabolism
Oxides - metabolism
oxygen
stable isotopes
sulfites
Thiophenes - metabolism
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Zusammenfassung: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 18O2 labeling studies.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.6b00583