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ID 115059
著者
Yamanomoto, Ken Tokushima University
Kita, Hazuki Tokushima University
田中, 正己 Tokushima Bunri University
Haraguchi, Naoki Toyohashi University of Technology
Itsuno, Shinichi Toyohashi University of Technology
資料タイプ
学術雑誌論文
抄録
Simulation of the monooxygenation function of flavoenzyme (Fl-Enz) has been long-studied with N5-modified cationic flavins (FlEt+), but never with N5-unmodified neutral flavins (Fl) despite the fact that Fl is genuinely equal to the active center of Fl-Enz. This is because of the greater lability of 4a-hydroperoxy adduct of Fl, FlOOH, compared to those of FlEt+, FlEtOOH, and Fl-Enz, FlOOH-Enz. In this study, Fl incorporated into a short peptide, flavopeptide (Fl-Pep), was designed by a rational top-down approach using a computational method, which could stabilize the corresponding 4a-hydroperoxy adduct (FlOOH-Pep) through intramolecular hydrogen bonds. We report catalytic chemoselective sulfoxidation as well as Baeyer–Villiger oxidation by means of Fl-Pep under light-shielding and aerobic conditions, which are the first Fl-Enz-mimetic aerobic oxygenation reactions catalyzed by Fl under non-enzymatic conditions.
掲載誌名
Chemical Science
ISSN
20416539
出版者
The Royal Society of Chemistry
8
8
開始ページ
5468
終了ページ
5475
発行日
2017-05-30
権利情報
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence(https://creativecommons.org/licenses/by/3.0/).
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言語
eng
著者版フラグ
出版社版
部局
理工学系
教養教育院