Lipase behavior in the stereoselective transesterification of zingerol-like derivatives and related biphenyls

Using a highly stereoselective enzymatic procedure based on the irreversible transesterification of alcoholic functions in organic solvent, both enantiomers of zingerol and dehydrozingerol O-methyl derivatives 1 and 2 were obtained in high optical purity. The biocatalytic method was then extended to the corresponding biphenyl derivatives 5–8 for which an one-pot resolution/desymmetrization was carried out on the whole racemic/meso mixtures to give single stereoisomers with very high enantiomeric and diastereoisomeric excesses. The comparison of kinetic and enantioselective behavior of the lipase AK from Pseudomonas fluorescens in the transesterification of monomer (±)-1 and the related (±)-5 and meso-6 biphenyl dimers was also made.

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► An enzymatic protocol was developed for kinetic resolution of zingerol derivatives.
► Simultaneous resolution/desymmetryzation was achieved for the related biphenyl diols.
► Kinetic evaluation of lipase activity was comparatively carried out.