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

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.

authors

• Begley, Tadhg

published proceedings

• J Am Chem Soc

author list (cited authors)

• Adak, S., & Begley, T. P.

citation count

• 47

complete list of authors

• Adak, Sanjoy||Begley, Tadhg P

publication date

• May 2016

publisher

• American Chemical Society (ACS)  Publisher

published in

• Journal of the American Chemical Society  Journal

keywords

• Catalysis
• Chromatography, Liquid
• Flavins
• Mass Spectrometry
• Oxides
• Thiophenes

PubMed Central ID

• 27120486

Digital Object Identifier (DOI)

• 10.1021/jacs.6b00583

start page

• 6424

end page

• 6426

volume

• 138

issue

• 20

URL

• http://dx.doi.org/10.1021/jacs.6b00583