Flavin Catalyzed Oxidations of Sulfides and Amines with Molecular Oxygen

Abstract

Novel biomimetic, aerobic oxidation with an organocatalyst was performed. The oxidations of organic substrates such as sulfides, secondary amines, N-hydroxylamines, and tertiary amines with molecular oxygen (1 atm) or even in air in the presence of 5-ethyl-3-methyllumiflavinium perchlorate catalyst and hydrazine monohydrate in 2,2,2-trifluoroethanol occur highly efficiently to give the corresponding oxidized compounds in excellent yields along with water and molecular nitrogen, which are environmentally benign. The TON of the oxidation of sulfides amounts to 19 000.

Evolution of Vitamin B2 Biosynthesis. A Novel Class of Riboflavin Synthase in Archaea

“…They can catalyze redox processes involving one-and two-electron transitions but also a variety of non-redox reactions such as photorepair of thymidine dimers in photodamaged DNA and the dehydration of non-activated organic substrates. 36,37 More recently, they have also been shown to act as chromophores in blue light photoreceptors in plants and fungi. [38][39][40][41][42][43] On structural grounds, flavins and flavocoenzymes should have been able to cooperate with non-protein enzymes in a hypothetical RNA world.…”

Effect of Coenzyme Q10, Riboflavin and Niacin on Tamoxifen treated postmenopausal breast cancer women with special reference to blood chemistry profiles

“…In the recent years, there is a growing body of evidence on protective role of CoQ 10 in cardio-vascular diseases and cancer [14][15][16]. Riboflavin, in its active cofactor forms like flavin mononucleotide (FMN) and flavin adenine dinucleotide (FAD), participates in oxidation-reduction reactions in numerous metabolic pathways and in energy production via the respiratory chain [17]. Riboflavin captures reactive metabolites like Tamoxifen and carcinogens to form a complex and thereby, prevents formation of DNA adducts [18], DNA methylation and maintains genomic stability [19,20].…”

Aerobic Oxidation of Primary Amines to Oximes Catalyzed by DPPH and WO3/Al2O3

“…Selective catalytic oxidative transformations of secondary amines to nitrones [3,4] and imines [5,6] have been explored. However, selective catalytic oxidation of primary amines 1 to oximes 2 [see Eq.…”