Details
| Original language | English |
|---|---|
| Article number | e202200293 |
| Journal | CHEMBIOCHEM |
| Volume | 23 |
| Issue number | 15 |
| Early online date | 1 Jun 2022 |
| Publication status | Published - 3 Aug 2022 |
| Externally published | Yes |
Abstract
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 rac-bicyclo[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.
Keywords
- chemoenzymatic Baeyer-Villiger oxidation, kinetic resolution, Shape Language Modeling, temperature-dependent enantioselectivity
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Biochemistry, Genetics and Molecular Biology(all)
- Molecular Medicine
- Biochemistry, Genetics and Molecular Biology(all)
- Molecular Biology
- Chemistry(all)
- Organic Chemistry
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In: CHEMBIOCHEM, Vol. 23, No. 15, e202200293, 03.08.2022.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Exploring the Temperature Effect on Enantioselectivity of a Baeyer-Villiger Biooxidation by the 2,5-DKCMO Module
T2 - The SLM Approach
AU - Röllig, Robert
AU - Paul, Caroline E.
AU - Duquesne, Katia
AU - Kara, Selin
AU - Alphand, Véronique
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. NCBs were synthesized by M.Sc. Alice Guarneri (Wageningen University, The Netherlands) and kindly provided by C. E. Paul (Delft University, The Netherlands) Publisher Copyright: © 2022 The Authors. ChemBioChem published by Wiley-VCH GmbH.
PY - 2022/8/3
Y1 - 2022/8/3
N2 - 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 rac-bicyclo[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.
AB - 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 rac-bicyclo[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.
KW - chemoenzymatic Baeyer-Villiger oxidation
KW - kinetic resolution
KW - Shape Language Modeling
KW - temperature-dependent enantioselectivity
UR - http://www.scopus.com/inward/record.url?scp=85131912430&partnerID=8YFLogxK
U2 - 10.1002/cbic.202200293
DO - 10.1002/cbic.202200293
M3 - Article
C2 - 35648642
AN - SCOPUS:85131912430
VL - 23
JO - CHEMBIOCHEM
JF - CHEMBIOCHEM
SN - 1439-4227
IS - 15
M1 - e202200293
ER -