Articolo in rivista, 2013, ENG, 10.1016/j.molcatb.2013.01.007

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

Claudia Sanfilippo, Angela Patti, Maria Antonietta Dettori, Davide Fabbri, Giovanna Delogu

CNR - Istituto di Chimica Biomolecolare, Via Paolo Gaifami 18, I-95127 Catania, Italy CNR - Istituto di Chimica Biomolecolare, Traversa la Crucca 3, Regione Baldinca, I-07100 Sassari, Italy

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.

Journal of molecular catalysis. B, Enzymatic (Print) 90 , pp. 107–113

Keywords

Biphenyl; Desymmetrization; Kinetic resolution; Lipase; Zingerol derivative

CNR authors

Fabbri Davide Gaetano, Sanfilippo Claudia, Delogu Giovanna Maria, Dettori Maria Antonietta, Patti Angela

CNR institutes

ICB – Istituto di chimica biomolecolare