Biomimetic flavin-catalysed reactions for organic synthesis

H Iida, Y Imada, SI Murahashi - Organic & biomolecular chemistry, 2015 - pubs.rsc.org
Using simple riboflavin related compounds as biomimetic catalysts, catalytic oxidation of
various substrates with hydrogen peroxide or molecular oxygen can be performed …

Artificial flavin systems for chemoselective and stereoselective oxidations

R Cibulka - European Journal of Organic Chemistry, 2015 - Wiley Online Library
Flavinium salts, both isoalloxazinium and alloxazinium derivatives, are useful
organocatalysts of redox reactions, and particularly in recent years, the number of …

[HTML][HTML] Molecular Editing of Flavins for Catalysis

A Rehpenn, A Walter, G Storch - Synthesis, 2021 - thieme-connect.com
The diverse activity of flavoenzymes in organic transformations has fascinated researchers
for a long time. However, when applied outside an enzyme environment, the isolated flavin …

Comparison of riboflavin-derived flavinium salts applied to catalytic H 2 O 2 oxidations

T Sakai, T Kumoi, T Ishikawa, T Nitta… - Organic & Biomolecular …, 2018 - pubs.rsc.org
A series of flavinium salts, 5-ethylisoalloxazinium, 5-ethylalloxazinium, and 1, 10-ethylene-
bridged alloxazinium triflates, were prepared from commercially available riboflavin. This …

Self-assembled ion-pair organocatalysis–asymmetric Baeyer–Villiger oxidation mediated by flavinium–cinchona alkaloid dimer

PP Poudel, K Arimitsu, K Yamamoto - Chemical Communications, 2016 - pubs.rsc.org
An ion-pair catalyst generated by assembly of a chiral flavinium and a cinchona alkaloid
dimer for use in asymmetric Baeyer–Villiger oxidation is presented. Ion-pair formation is …

Methyl groups matter: Photo-CIDNP characterizations of the semiquinone radicals of FMN and demethylated FMN analogs

N Pompe, J Chen, B Illarionov, S Panter… - The Journal of …, 2019 - pubs.aip.org
In this contribution, the relative hyperfine couplings are determined for the 1 H nuclei of the
flavin mononucleotide (FMN) radical in an aqueous environment. In addition, three structural …

Two‐Phase Oxidations with Aqueous Hydrogen Peroxide Catalyzed by Amphiphilic Pyridinium and Diazinium Salts

T Hartman, J Šturala, R Cibulka - Advanced Synthesis & …, 2015 - Wiley Online Library
Amphiphilic pyridinium and diazinium salts were shown to be effective catalysts in two‐
phase (water/chloroform or water/dichloromethane) sulfoxidations and N‐oxidations with …

Chiral ethylene-bridged flavinium salts: the stereoselectivity of flavin-10a-hydroperoxide formation and the effect of substitution on the photochemical properties

J Žurek, E Svobodová, J Šturala, H Dvořáková… - Tetrahedron …, 2017 - Elsevier
A series of chiral non-racemic N 1, N 10-ethylene bridged flavinium salts 4 was prepared
using enantiomerically pure 2-substituted 2-aminoethanols (R= isopropyl, phenyl, benzyl, 4 …

Aerobic oxidation catalyzed by polyoxometalates associated to an artificial reductase at room temperature and in water

A Naim, Y Chevalier, Y Bouzidi, P Gairola… - Inorganic Chemistry …, 2020 - pubs.rsc.org
Four polyoxometalates (POMs) were combined with an artificial reductase based on
polyethyleneimine (PEI) and flavin mononucleotide (FMN) which is capable of delivering …

Anion effect of 5-ethylisoalloxazinium salts on flavin-catalyzed oxidations with H2O2

H Iida, T Ishikawa, K Nomura, SI Murahashi - Tetrahedron Letters, 2016 - Elsevier
The anion effect of the 5-ethylisoalloxazinium salts on their catalytic activity was investigated
for the oxidation of sulfide with aq H 2 O 2 in order to design more practical and safer …