Dibenzothiophene Catabolism Proceeds via a Flavin-N5-oxide Intermediate.

ABSTRACT: 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.

SUBMITTER: Adak S 

PROVIDER: S-EPMC6078383 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature