Chemoenzymatic deracemization of lisofylline catalyzed by a (laccase/TEMPO)-alcohol dehydrogenase system

Abstract

Lisofylline (LSF) is a synthetic methylxanthine active agent exhibiting potent anti-inflammatory and immunomodulatory properties; therefore, it has been widely investigated as a promising drug candidate for treating various autoimmune disorders,...

Eco-friendly TEMPO/laccase/O2 biocatalytic system for degradation of Indigo Carmine: operative conditions and laccase inactivation

“…21 Many applications of this system have been proposed over the past twenty years, including bioremediation and detoxification of environmental pollutants, 22–24 aerobic oxidation of non-phenolic substrates, 14,19,21,25 selective oxidative modification of cellulose, 18,26 sugars, 27 cellulose nanofiber production, 28 biocatalyzed organic synthesis, including transformation of biomass into compounds with high added value. 29–35…”

“…21 Many applications of this system have been proposed over the past twenty years, including bioremediation and detoxication of environmental pollutants, [22][23][24] aerobic oxidation of non-phenolic substrates, 14,19,21,25 selective oxidative modication of cellulose, 18,26 sugars, 27 cellulose nanober production, 28 biocatalyzed organic synthesis, including transformation of biomass into compounds with high added value. [29][30][31][32][33][34][35] The mechanistic details of laccase/TEMPO catalyzed aerobic oxidation of organic compounds is still a matter of discussion. [17][18][19]36,37 According with the proposed ionic mechanism, 17,18,21,36 laccase oxidizes TEMPO with concomitant fourelectron reduction of molecular oxygen to water.…”

4‐OH‐TEMPO radical grafted onto a novel polyaromatic ether sulfone containing carboxyl side chains as solid catalyst for alcohol oxidation

“…2,2,6,6‐Tetramethylpiperidin‐1‐oxygen free radical (TEMPO), as a photothermal stable nitrogen and oxygen free radical, has been widely used in the selective oxidation of alcohols because of its merits like mild reaction conditions, high selectivity as well as high conversion 13 . Recently, various catalysts including TEMPO, TEMPO/NaBr/NaOCl systems 14 and TEMPO/laccase 15–17 . TEMPO Br 2 /NaNO 2.…”

“…13 Recently, various catalysts including TEMPO, TEMPO/NaBr/NaOCl systems 14 and TEMPO/laccase. [15][16][17] TEMPO/bimetallic salt system, 21,22 TEMPO/FeC1 3 /NaN0 2 NaNO 2, 23 TEMPO/Cu microreaction, 24 etc. have showed excellent catalytic performance in the selective oxidation of alcohols with molecular oxygen as oxidant.…”

Deracemization of racemic alcohols combining photooxidation and biocatalytic reduction

“…6 For example, Kroutil and coworkers have reported on developing a sequential chemoenzymatic one-pot two-step deracemization protocol for racemic lisofylline (LSF) which is widely investigated as a promising drug candidate for treating various autoimmune disorders, including type 1 diabetes. 7 Hu's lab has developed a catalytic deracemization method for secondary benzylic alcohols which is based on sequential photochemical dehydrogenation followed by enantioselective thermal hydrogenation. 8 Although these elegant methods have been reported, developing other efficient methods to extend the tool library of alcohol deracemization is still meaningful.…”