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

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Autoren

  • Robert Röllig
  • Caroline E. Paul
  • Katia Duquesne
  • Selin Kara
  • Véronique Alphand

Externe Organisationen

  • Universite d'Aix-Marseille
  • Aarhus University
  • Delft University of Technology
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Details

OriginalspracheEnglisch
Aufsatznummere202200293
FachzeitschriftCHEMBIOCHEM
Jahrgang23
Ausgabenummer15
Frühes Online-Datum1 Juni 2022
PublikationsstatusVeröffentlicht - 3 Aug. 2022
Extern publiziertJa

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.

ASJC Scopus Sachgebiete

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Exploring the Temperature Effect on Enantioselectivity of a Baeyer-Villiger Biooxidation by the 2,5-DKCMO Module: The SLM Approach. / Röllig, Robert; Paul, Caroline E.; Duquesne, Katia et al.
in: CHEMBIOCHEM, Jahrgang 23, Nr. 15, e202200293, 03.08.2022.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Röllig R, Paul CE, Duquesne K, Kara S, Alphand V. Exploring the Temperature Effect on Enantioselectivity of a Baeyer-Villiger Biooxidation by the 2,5-DKCMO Module: The SLM Approach. CHEMBIOCHEM. 2022 Aug 3;23(15):e202200293. Epub 2022 Jun 1. doi: 10.1002/cbic.202200293
Röllig, Robert ; Paul, Caroline E. ; Duquesne, Katia et al. / Exploring the Temperature Effect on Enantioselectivity of a Baeyer-Villiger Biooxidation by the 2,5-DKCMO Module : The SLM Approach. in: CHEMBIOCHEM. 2022 ; Jahrgang 23, Nr. 15.
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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 {\textquoteleft}Shape Language Modelling{\textquoteright} (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.",
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T2 - The SLM Approach

AU - Röllig, Robert

AU - Paul, Caroline E.

AU - Duquesne, Katia

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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.

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Y1 - 2022/8/3

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