Dibenzothiophene Catabolism Proceeds via a Flavin-N5-oxide Intermediate

被引：48

作者：

Adak, Sanjoy ^{[1
]}

Begley, Tadhg P. ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, 3255 TAMU, College Stn, TX 77843 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 20期

基金：

美国国家卫生研究院;

关键词：

CRYSTAL-STRUCTURE; FOSSIL-FUELS; DESULFURIZATION; RIBOFLAVIN; MECHANISMS; OXIDATION;

D O I：

10.1021/jacs.6b00583

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 O-18(2) labeling studies.

引用

页码：6424 / 6426

页数：3

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