Design of peptide-containing N 5-unmodified neutral flavins that catalyze aerobic oxygenations

Chemical Science
Yukihiro ArakawaYasushi Imada

Abstract

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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Citations

Oct 26, 2018·Angewandte Chemie·Yoan ChevalierFrédéric Avenier
Nov 30, 2018·Photochemistry and Photobiology·John LeeAntonie J W G Visser
Sep 25, 2019·Angewandte Chemie·Jan Sietmann, Johannes M Wahl
Apr 22, 2020·Chemical Communications : Chem Comm·Yukihiro ArakawaYasushi Imada
May 14, 2019·Frontiers in Chemistry·Leander Crocker, Ljiljana Fruk
May 17, 2018·Organic & Biomolecular Chemistry·Takuya SakaiHiroki Iida
Jul 10, 2018·ACS Applied Materials & Interfaces·Keigo KamataMichikazu Hara

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Methods Mentioned

BETA
NMR

Software Mentioned

Pep
Fl

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