15800-90-5Relevant academic research and scientific papers
Robust Photocatalytic Method Using Ethylene-Bridged Flavinium Salts for the Aerobic Oxidation of Unactivated Benzylic Substrates
Pokluda, Adam,Anwar, Zubair,Boguschová, Veronika,Anusiewicz, Iwona,Skurski, Piotr,Sikorski, Marek,Cibulka, Radek
supporting information, p. 4371 - 4379 (2021/04/02)
7,8-Dimethoxy-3-methyl-1,10-ethylenealloxazinium chloride (1a) was found to be a superior photooxidation catalyst among substituted ethylene-bridged flavinium salts (R=7,8-diMeO, 7,8-OCH2O-, 7,8-diMe, H, 7,8-diCl, 7-CF3 and 8-CF3). Selection was carried out based on structure vs catalytic activity and properties relationship investigations. Flavinium salt 1a proved to be robust enough for practical applications in benzylic oxidations/oxygenations, which was demonstrated using a series of substrates with high oxidation potential, i. e., 1-phenylethanol, ethylbenzene, diphenylmethane and diphenylmethanol derivatives substituted with electron-withdrawing groups (Cl or CF3). The unique capabilities of 1a can be attributed to its high photostability and participation via a relatively long-lived singlet excited state, which was confirmed using spectroscopic studies, electrochemical measurements and TD-DFT calculations. This allows the maximum use of the oxidation power of 1a, which is given by its singlet excited state reduction potential of +2.4 V. 7,8-Dichloro-3-methyl-1,10-ethylenealloxazinium chloride (1 h) can be used as an alternative photocatalyst for even more difficult substrates. (Figure presented.).
Regulating Cofactor Balance In Vivo with a Synthetic Flavin Analogue
Tan, Zhuotao,Zhu, Chenjie,Fu, Jingwen,Zhang, Xiaowang,Li, Ming,Zhuang, Wei,Ying, Hanjie
, p. 16464 - 16468 (2018/11/23)
A novel strategy to regulate cofactor balance in vivo for whole-cell biotransformation using a synthetic flavin analogue is reported. High efficiency, easy operation, and good applicability were observed for this system. Confocal laser scanning microscopy was employed to verify that the synthetic flavin analogue can directly permeate into Escherichia coli cells without modifying the cell membrane. This work provides a promising intracellular redox regulatory approach to construct more efficient cell factories.
CHEMICAL REGENERATION METHOD OF OXIDIZED COENZYME NAD (P)+
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, (2017/07/06)
It discloses a chemical regeneration method of oxidized coenzyme NAD(P)+ which is under an oxygen or air atmosphere condition, adding a catalytic amount of bridged flavin, and oxidizing NAD(P)H to obtain NAD(P)+. The catalyst for regeneration of cofactor is cheap and easily available small organic molecule having no noble metal; this regeneration system can regenerate NADH and NADPH; this regeneration system has a wide pH range and temperature range, being applicable to various oxidation reactions catalyzed by nicotinamide-dependent oxidoreductase.
N1,N10-Ethylene-bridged high-potential flavins: Synthesis, characterization, and reactivity
Li, Wen-Shan,Zhang, Nanjing,Sayre, Lawrence M.
, p. 4507 - 4522 (2007/10/03)
N1,N10-Ethyleneisoalloxazinium chloride and its 8-Cl-, 7-CF3-, and 3-CH3-7-CF3-substituted analogs were synthesized for the purpose of exhibiting thermal reactivity with organic substrates. The new flavins were characterized spectroscopically and electrochemically, and were found to react with amines, thiols, and phenylhydrazine, the latter case exhibiting catalytic aerobic recycling. Reactions of aliphatic benzylic and cyclopropyl amines with the 7-CF3 analog were also compared to their oxidations by tris(phenanthroline)iron(III). All reactions of the flavinium salts appear to occur through heterolytic rather than homolytic mechanisms.
