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

Jaeho Yoon, S.H. Lee, Florian Tieves, Marine Rauch, Frank Hollmann, Chan Beum Park

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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.

Original languageEnglish
Pages (from-to)5632-5637
JournalACS Sustainable Chemistry and Engineering
Volume7
Issue number6
DOIs
Publication statusPublished - 2019

Keywords

  • Alginate hydrogel
  • Asymmetric hydrogenation
  • Ene-reductase
  • NADH-free bioprocess
  • Photobiocatalysis

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