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Light-Harvesting Dye–Alginate Hydrogel for Solar-Driven, Sustainable Biocatalysis of Asymmetric Hydrogenation

Author:
Yoon, Jaeho, Lee, Sahng Ha, Tieves, Florian, Rauch, Marine, Hollmann, Frank, Park, Chan Beum
Source:
ACS sustainable chemistry & engineering 2019 v.7 no.6 pp. 5632-5637
ISSN:
2168-0485
Subject:
NAD (coenzyme), Thermus scotoductus, alginates, biocatalysis, enantiomers, encapsulation, energy, enzymes, heat, hydrogels, hydrogenation, lighting, value added
Abstract:
We report visible light-driven, asymmetric hydrogenation of C═C bonds using an ene-reductase from Thermus scotoductus SA-01 (TsOYE) and a light-harvesting dye (rose bengal, RB) co-immobilized in an alginate hydrogel. Highly efficient encapsulation of RB in alginate hydrogel was achieved using the intrinsic affinity between TsOYE and RB, which allowed for the construction of robust RB-TsOYE-loaded alginate capsules. In the absence of NADH, the photobiocatalytic system facilitated asymmetric reduction of 2-methylcyclohexenone to an enantiopure (R)-2-methylcyclohexanone (ee > 99%; max. conversion, 70.4%; turnover frequency, 1.54 min–¹; turnover number, 300.2) under illumination. A series of stability tests revealed a significant enhancement of TsOYE’s robustness in alginate hydrogel against heat and chemical denaturants. This study provides insight into a greener and sustainable approach of cofactor-free OYE catalysis for producing value-added chemicals using light energy.
Agid:
6330713