ID | 115059 |
Author |
Arakawa, Yukihiro
Tokushima University
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Yamanomoto, Ken
Tokushima University
Kita, Hazuki
Tokushima University
Minagawa, Keiji
Tokushima University
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Tanaka, Masami
Tokushima Bunri University
Haraguchi, Naoki
Toyohashi University of Technology
Itsuno, Shinichi
Toyohashi University of Technology
Imada, Yasushi
Tokushima University
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Content Type |
Journal Article
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Description | 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.
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Journal Title |
Chemical Science
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ISSN | 20416539
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Publisher | The Royal Society of Chemistry
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Volume | 8
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Issue | 8
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Start Page | 5468
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End Page | 5475
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Published Date | 2017-05-30
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Rights | This article is licensed under a Creative Commons Attribution 3.0 Unported Licence(https://creativecommons.org/licenses/by/3.0/).
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EDB ID | |
DOI (Published Version) | |
URL ( Publisher's Version ) | |
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language |
eng
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TextVersion |
Publisher
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departments |
Science and Technology
Liberal Arts and Sciences
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