Details
| Original language | English |
|---|---|
| Pages (from-to) | 2761-2765 |
| Number of pages | 5 |
| Journal | Organic Process Research & Development |
| Volume | 26 |
| Issue number | 9 |
| Early online date | 11 Aug 2022 |
| Publication status | Published - 16 Sept 2022 |
Abstract
The ability of unspecific peroxygenase (UPO) to hydroxylate a wide range of substrates with just H2O2 as a cosubstrate has attracted a great deal of attention in biocatalytic research. The enzyme's intrinsic limitation to be inactivated by excess amounts of the oxidative cosubstrate has been tackled with in or ex situ hydrogen peroxide (H2O2) provision strategies. In this paper, we present the application of the covalently immobilized UPO mutant PaDa-I in a rotating bed reactor for the hydroxylation of ethylbenzene in a two-liquid-phase system. By monitoring product formation in the organic phase and H2O2 concentration in the aqueous phase, the multiphasic reaction was optimized. Over 58 h, up to 414 mM (R)-1-phenylethanol was accumulated in the organic phase, corresponding to a productivity of 436 mg L-1 h-1 and a selectivity for the alcohol product over the overoxidated ketone product of 62%. It was found that the overoxidation of (R)-1-phenylethanol to acetophenone resulted in part from the H2O2 concentration in the aqueous phase but mainly from the concentration of the target alcohol. Therefore, a repetitive batch was performed over five times for 13 h with similar product concentrations and formation rates as in the conventional approach but a considerably higher selectivity of 79%.
Keywords
- biphasic system, fed-batch synthesis, oxyfunctionalization, peroxygenase, rotating bed reactor
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic Process Research & Development, Vol. 26, No. 9, 16.09.2022, p. 2761-2765.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Peroxygenase-Driven Ethylbenzene Hydroxylation in a Rotating Bed Reactor
AU - Hobisch, Markus
AU - Santis, Piera De
AU - Serban, Simona
AU - Basso, Alessandra
AU - Byström, Emil
AU - Kara, Selin
N1 - Funding Information: This project has received funding from the European Union’s Horizon 2020 research and innovation program under the Marie Skłodowska–Curie Grant Agreement No. 764920. Independent Research Fund Denmark (PHOTOX- f project, Grant No. 9063-00031B) was gratefully acknowledged for the grant funding.
PY - 2022/9/16
Y1 - 2022/9/16
N2 - The ability of unspecific peroxygenase (UPO) to hydroxylate a wide range of substrates with just H2O2 as a cosubstrate has attracted a great deal of attention in biocatalytic research. The enzyme's intrinsic limitation to be inactivated by excess amounts of the oxidative cosubstrate has been tackled with in or ex situ hydrogen peroxide (H2O2) provision strategies. In this paper, we present the application of the covalently immobilized UPO mutant PaDa-I in a rotating bed reactor for the hydroxylation of ethylbenzene in a two-liquid-phase system. By monitoring product formation in the organic phase and H2O2 concentration in the aqueous phase, the multiphasic reaction was optimized. Over 58 h, up to 414 mM (R)-1-phenylethanol was accumulated in the organic phase, corresponding to a productivity of 436 mg L-1 h-1 and a selectivity for the alcohol product over the overoxidated ketone product of 62%. It was found that the overoxidation of (R)-1-phenylethanol to acetophenone resulted in part from the H2O2 concentration in the aqueous phase but mainly from the concentration of the target alcohol. Therefore, a repetitive batch was performed over five times for 13 h with similar product concentrations and formation rates as in the conventional approach but a considerably higher selectivity of 79%.
AB - The ability of unspecific peroxygenase (UPO) to hydroxylate a wide range of substrates with just H2O2 as a cosubstrate has attracted a great deal of attention in biocatalytic research. The enzyme's intrinsic limitation to be inactivated by excess amounts of the oxidative cosubstrate has been tackled with in or ex situ hydrogen peroxide (H2O2) provision strategies. In this paper, we present the application of the covalently immobilized UPO mutant PaDa-I in a rotating bed reactor for the hydroxylation of ethylbenzene in a two-liquid-phase system. By monitoring product formation in the organic phase and H2O2 concentration in the aqueous phase, the multiphasic reaction was optimized. Over 58 h, up to 414 mM (R)-1-phenylethanol was accumulated in the organic phase, corresponding to a productivity of 436 mg L-1 h-1 and a selectivity for the alcohol product over the overoxidated ketone product of 62%. It was found that the overoxidation of (R)-1-phenylethanol to acetophenone resulted in part from the H2O2 concentration in the aqueous phase but mainly from the concentration of the target alcohol. Therefore, a repetitive batch was performed over five times for 13 h with similar product concentrations and formation rates as in the conventional approach but a considerably higher selectivity of 79%.
KW - biphasic system
KW - fed-batch synthesis
KW - oxyfunctionalization
KW - peroxygenase
KW - rotating bed reactor
UR - http://www.scopus.com/inward/record.url?scp=85136667210&partnerID=8YFLogxK
U2 - 10.1021/acs.oprd.2c00211
DO - 10.1021/acs.oprd.2c00211
M3 - Article
VL - 26
SP - 2761
EP - 2765
JO - Organic Process Research & Development
JF - Organic Process Research & Development
SN - 1520-586X
IS - 9
ER -