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 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 (18)O2 labeling studies.
Department of Chemistry, Texas A&M University , 3255 TAMU, College Station, Texas 77843, United States.
Sanjoy
S
Adak
Department of Chemistry, Texas A&M University , 3255 TAMU, College Station, Texas 77843, United States.
Tadhg P
TP
Begley
D002384:Catalysis; D002853:Chromatography, Liquid; D005415:Flavins / Q000378:metabolism*; D013058:Mass Spectrometry; D010087:Oxides / Q000378:metabolism; D013876:Thiophenes / Q000378:metabolism*
D005415:Flavins; D010087:Oxides; D013876:Thiophenes; C016366:dibenzothiophene