Exploring the Temperature Effect on Enantioselectivity of a Baeyer‐Villiger Biooxidation by the 2,5‐DKCMO Module: The SLM Approach

Robert Röllig (1, 2) , Caroline Paul (3) , Katia Duquesne (1, 2) , Selin Kara (4) , Véronique Alphand (1, 2)

1 AMU - Aix Marseille Université
2 ISM2 - Institut des Sciences Moléculaires de Marseille
3 Catalysis Engineering - ChemE, Delft University of Technology, Van der Maasweg 9, 2629HZ Delft
4 Aarhus University [Aarhus]

Temperature is a crucial parameter for biological and chemical processes. Its effect on enzymatically catalysed reactions has been known for decades, and stereo-and enantiopreference are often temperature-dependent. For the first time, we present the temperature effect on the Baeyer-Villiger oxidation of racbicyclo[3.2.0]hept-2-en-6-one by the type II Bayer-Villiger monooxygenase, 2,5-DKCMO. In the absence of a reductase and driven by the hydride-donation of a synthetic nicotinamide analogue, the clear trend for a decreasing enantioselectivity at higher temperatures was observed. "Traditional" approaches such as the determination of the enantiomeric ratio (E) appeared unsuitable due to the complexity of the system. To quantify the trend, we chose to use the 'Shape Language Modelling' (SLM), a tool that allows the reaction to be described at all points in a shape prescriptive manner. Thus, without knowing the equation of the reaction, the substrate ee can be estimated that at any conversion.

Domaines: Biotechnologies; Chimie organique; Autre

Robert Röllig, Caroline Paul, Katia Duquesne, Selin Kara, Véronique Alphand. Exploring the Temperature Effect on Enantioselectivity of a Baeyer‐Villiger Biooxidation by the 2,5‐DKCMO Module: The SLM Approach. ChemBioChem, 2022, 23 (15), ⟨10.1002/cbic.202200293⟩. ⟨hal-03784017⟩