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Application L2306

Selective peroxygenase-catalysed oxidation of toluene derivatives to benzaldehydes

Yutong Wang, Niklas Teetz, Dirk Holtmann, Miguel Alcalde, Jacob M. A. van Hengst, Xiaoxiao Liu, Mengfan Wang, Wei Qi, Wuyuan Zhang, and Frank Hollmann

ChemCatChem, 2023, 15(13), e202300645.

“Biocatalytic oxidation reactions of toluene derivates to the corresponding aldehydes are typically challenged by regio- and chemoselectivity issues. In this contribution we address both challenges by a combined reactant- and reaction engineering approach. We demonstrate that the peroxygenase-catalysed transformation of ring-substituted toluenes proceeds highly regioselectively in benzylic position. Furthermore, neat reaction conditions not only enable attractive product concentrations (up to 185 mM) but also result in highly chemoselective oxidations to the aldehyde level.”

Highlight:

  • “For the scale-up reaction, model substrate p-Cl-toluene was used as starting material, and rotating bed reactor (RBR) was utilised to conduct the reaction. Specifically, the reaction was conducted in a SpinChem Vessel S2 (200 mL) using a SpinChem RBR S2 rotating bed (SpinChem AB, Sweden). The rotating bed was loaded with 18 g imm-AaeUPO, and the reactor was filled with 120 mL p-Cl-toluene. The rotating bed was adjusted to be 1 cm above the reactor bottom, and the reaction was run at 400 rpm and 30 °C. tBuOOH (600 mM in n-decane) was fed with syringe pump 2 mL.h-1.”

 

Authors & Research Group:

This research was conducted by an international collaboration between Delft University of Technology in the Netherlands, DECHEMA Forschungsinstitut in Germany, and Spanish National Research Council (CSIC) in Spain, bringing together expertise in biocatalysis, enzyme engineering, and oxidative biotransformations.

Principal Investigator:

Frank Hollmann – Department of Biotechnology, Delft University of Technology, Netherlands | LinkedIn, Specialization: Biocatalysis and enzymatic oxidations

Research Team:

Yutong Wang – Department of Biotechnology, Delft University of Technology | LinkedIn

Niklas Teetz – DECHEMA Forschungsinstitut, Industrial Biotechnology | LinkedIn

Dirk Holtmann – DECHEMA Forschungsinstitut, Industrial Biotechnology | LinkedIn

Miguel Alcalde – Institute of Catalysis and Petrochemistry, Spanish National Research Council (CSIC) | LinkedIn

Jacob M. A. van Hengst – Department of Biotechnology, Delft University of Technology | LinkedIn

Xiaoxiao Liu – Department of Biotechnology, Delft University of Technology 

Mengfan Wang – Department of Biotechnology, Delft University of Technology

Wei Qi – Department of Biotechnology, Delft University of Technology

Wuyanan Zhang – Department of Biotechnology, Delft University of Technology