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Updated: Jan 18, 2026

Anaerobic Protein Purification and Kinetic Analysis via Oxygen Electrode for Studying DesB Dioxygenase Activity and Inhibition
Published on: October 3, 2018
Exploring Unspecific Peroxygenase Selectivity with Diverse Hydrocarbon Substrates
Essi Rytkönen1, Nina Hakulinen1, Janne Jänis1
1Department of Chemistry, University of Eastern Finland, P.O. Box 111, FI-80101, Joensuu, Finland.
Abstract:
Unspecific peroxygenases (UPOs) are enzymes capable of oxidising various substrates using hydrogen peroxide as a co-substrate. UPOs have gained interest due to their broad substrate specificity, which includes relatively inexpensive precursors for valuable compounds, such as pharmaceuticals and chemical building blocks. In this study, the activity of a panel of 30 UPOs toward aliphatic and aromatic hydrocarbons was screened to assess variation in substrate selectivity. Most of the studied UPOs were able to oxidise the substrates efficiently, producing 2-5 products via hydrogen abstraction or epoxidation. Overall trends were observed, such as the preference for aromatic oxidation over benzylic hydroxylation in the case of toluene, while the opposite was observed with ethylbenzene. Different UPOs could also be categorized based on their reaction profiles with all substrates. Selectivity was generally low, as oxyfunctionalization reactions led to mixtures of products that were further oxidised. However, styrene and cyclohexene were converted rather exclusively to their epoxide products. The results indicate that the substrate scope of UPOs includes various types of hydrocarbons, which are oxidised depending on the individual enzyme's active site. They also hold potential for producing chemicals for industrial purposes more sustainably, but their selectivity should first be improved through protein engineering.
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Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

