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

doi:10.1021/acssuschemeng.9b01075

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^*

^*Corresponding author for this work

BT/Biocatalysis

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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 language	English
Pages (from-to)	5632-5637
Journal	ACS Sustainable Chemistry and Engineering
Volume	7
Issue number	6
DOIs	https://doi.org/10.1021/acssuschemeng.9b01075
Publication status	Published - 2019

Bibliographical note

Green Open Access added to TU Delft Institutional Repository ‘You share, we take care!’ – Taverne project https://www.openaccess.nl/en/you-share-we-take-care Otherwise as indicated in the copyright section: the publisher is the copyright holder of this work and the author uses the Dutch legislation to make this work public.

Keywords

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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

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. ",

keywords = "Alginate hydrogel, Asymmetric hydrogenation, Ene-reductase, NADH-free bioprocess, Photobiocatalysis",

author = "Jaeho Yoon and S.H. Lee and Florian Tieves and Marine Rauch and Frank Hollmann and Park, {Chan Beum}",

note = "Green Open Access added to TU Delft Institutional Repository {\textquoteleft}You share, we take care!{\textquoteright} – Taverne project https://www.openaccess.nl/en/you-share-we-take-care Otherwise as indicated in the copyright section: the publisher is the copyright holder of this work and the author uses the Dutch legislation to make this work public.",

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language = "English",

volume = "7",

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publisher = "American Chemical Society (ACS)",

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AU - Yoon, Jaeho

AU - Lee, S.H.

AU - Tieves, Florian

AU - Rauch, Marine

AU - Hollmann, Frank

AU - Park, Chan Beum

N1 - Green Open Access added to TU Delft Institutional Repository ‘You share, we take care!’ – Taverne project https://www.openaccess.nl/en/you-share-we-take-care Otherwise as indicated in the copyright section: the publisher is the copyright holder of this work and the author uses the Dutch legislation to make this work public.

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

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KW - Asymmetric hydrogenation

KW - Ene-reductase

KW - NADH-free bioprocess

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

Abstract

Bibliographical note

Keywords

UN SDGs

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