Development of compatible photocatalyst-enzyme hybrid system via Intensifying enzyme tolerance for enhanced chiral alcohol synthesis
Photo-enzyme catalysis featuring sustainability and selectivity is attractive, but remains challenges from efficiency and enzyme inactivation. This work provides a compatible and efficient photocatalyst-enzyme hybrid system for chiral alcohol synthesis. A covalent organic framework (COF) possessing broad visible light absorption edge to 554 nm was used for photocatalytic NADPH regeneration, achieving 82 % yield in 90 min. Then the influence of photocatalysis on coupled enzyme Lb ADH was unveiled by fluorescence spectra and circular dichroism. Further a facile and mild strategy of entrapping Lb ADH into Ca 2+ /Mn 2+ doped alginate gel was carried out. Impressively, enzyme immobilized strategy not only enhances 3.2 times activity, but also protects Lb ADH from diverse harsh environments, thereby improving photo-enzyme catalytic yield from 26 % to 82 %. To our delight, this one-pot photo-enzyme catalytic system achieves highly yield (up to 99 %) with excellent enantioselectivity (90–99 ee %) for various chiral alcohols, and fulfills semipreparative scale preparation of ( R )-1-[3,5-Bis(trifluoromethyl)phenyl] ethanol, prochiral intermediate of Aprepitant. This work sheds light on the new synthetic route of chiral compounds and development of photo-enzyme catalytic field.
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