Articolo in rivista, 2021, ENG, 10.1016/j.bioorg.2021.105014

Biocatalytic regio- and stereoselective access to ?-3 endocannabinoid epoxides with peroxygenase from oat flour

Sanfilippo C.; Patti A.

CNR - Istituto di Chimica Biomolecolare, Via Paolo Gaifami 18, Catania, I-95126, CNR - Istituto di Chimica Biomolecolare, Via Paolo Gaifami 18, I-95126 Catania, Italy, , Italy

The biocatalytic epoxidation of ethanolamides of ?-3 fatty acids EPA and DHA, regarded as biologically active ?-3 endocannabinoids, in the presence of a peroxygenase-containing preparation from oat flour was investigated. Good regio- and steroselectivity toward the formation of the epoxide on the terminal double bond in the chain was observed with both these fatty acid derivatives and chiral monoepoxides 1 or 2 in 74% optical purity and 51-53% yields were isolated and spectroscopically characterized. The use of acetone as cosolvent in the reaction medium allowed to increase the concentration of starting substrates up to 40 mM and to further improve the selectivity in the epoxidation of DHA-EA. Due to the easy availability of the enzymatic preparation, the method offers a valuable strategy for the access to oxyfunctionalized derivatives of fatty acids.

Bioorganic chemistry (Print) 113 , pp. 105014–?

Keywords

Peroxygenase Epoxidation Polyunsaturated fatty acids ?-3 Endocannabinoids Oat flour

CNR authors

Sanfilippo Claudia, Patti Angela

CNR institutes

ICB – Istituto di chimica biomolecolare