ID 113071
Author
Yamanomoto, Ken Tokushima University
Kita, Hazuki Tokushima University
Keywords
Aerobic oxygenation
Baeyer-Villiger oxidation
Biomimetic catalyst
Flavin
Peptide
Content Type
Journal Article
Description
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.
Journal Title
CHIMIA
ISSN
00094293
NCID
AA00603792
Publisher
Swiss Chemical Society
Volume
72
Issue
12
Start Page
866
End Page
869
Published Date
2018-12-01
Remark
論文本文は2019-12-01以降公開予定
Rights
©Swiss Chemical Society: CHIMIA, volume72, No.12, page866-869 (2018), doi:10.2533/chimia.2018.866
EDB ID
DOI (Published Version)
URL ( Publisher's Version )
language
eng
TextVersion
その他
departments
Science and Technology
Liberal Arts and Sciences