Sustainable synthesis of chiral alpha-hydroxy ketones via dynamic kinetic resolution
Chiral α-hydroxy ketones are important building blocks for the synthesis of several biologically active compounds such as pharmaceuticals, agrochemicals, and pheromones. Various chemical and biocatalytical approaches for their synthesis are described in literature. Among the enzymatic strategies kinetic resolution of racemic α-hydroxy ketones catalyzed by lipases is advantageous as there is no need for a coenzyme or a cofactor and high substrate loadings are possible thanks to comparably high stability of lipases in organic solvents. Typical disadvantages of kinetic resolutions are a maximum conversion of 50% and difficult product purification. However, both can be eliminated by establishing a dynamic kinetic resolution (DKR) by coupling a lipase with a chemo-catalyst.
The aim of this project is the establishment of an effective synthesis for interesting alpha-hydroxy ketones. The focus is on the following parameters:
- selection of suitable biocatalysts and chemo-catalysts
- immobilization of the biocatalysts
- choice of reaction media
- the water activity
- reaction temperature
- combining suitable reaction conditions of both catalysts
For all parameters the activities of both catalyst, the stability of the biocatalysts and the yield and enantiomeric excess of the products are evaluated.
Project partner:
Chiracon GmbH, Luckenwalde, Germany
Enzymicals AG, Greifswald, Germany
Funding:
AiF-ZIM (SynKat-Alpha, KF3068202AJ4)