ID 113071
著者
Yamanomoto, Ken Tokushima University
Kita, Hazuki Tokushima University
キーワード
Aerobic oxygenation
Baeyer-Villiger oxidation
Biomimetic catalyst
Flavin
Peptide
資料タイプ
学術雑誌論文
抄録
We recently developed a flavopeptide immobilized on polystyrene resin, Fl-Pep-PS, that could realize the first N5-unmodified neutral flavin (Fl)-catalyzed aerobic oxygenation reactions under non-enzymatic conditions. Although a key active species is assumed to be the corresponding 4a-hydroperoxyflavin (Fl4aOOH) from the unprecedented activity and unique chemoselectivity, further circumstantial support would be helpful to be sure since spectroscopic evidence is difficult to obtain due to the compound’s insolubility. In this article, we report that the aerobic Baeyer-Villiger oxidation of a fused cyclobutanone, (±)-cis-bicyclo[3.2.0]hept-2-en-6-one (1), can be promoted with Fl-Pep-PS in a FMO-like chemoselectivity and regiodivergent manner via Fl-related catalytic intermediates, which delivers strong evidence of the involvement of Fl4aOOH as an active species in Fl-Pep-PS-catalyzed aerobic oxygenation reactions.
掲載誌名
CHIMIA
ISSN
00094293
cat書誌ID
AA00603792
出版者
Swiss Chemical Society
72
12
開始ページ
866
終了ページ
869
発行日
2018-12-01
備考
論文本文は2019-12-01以降公開予定
権利情報
©Swiss Chemical Society: CHIMIA, volume72, No.12, page866-869 (2018), doi:10.2533/chimia.2018.866
EDB ID
出版社版DOI
出版社版URL
言語
eng
著者版フラグ
その他
部局
理工学系
教養教育院