title: Deracemization of secondary alcohols by chemo-enzymatic sequence with plant cells.
abstract: A screening based on undifferentiated plant cells allowed identifying Gardenia jasminoides as the best biocatalyst to perform the kinetic resolution of 1-phenylethanol. This species was further tested for its ability to oxidize stereoselectively the (S)-isomers from racemic mixtures of secondary alcohols leaving their antipodes unaffected in Tris-HCl buffer. Those substrates which afforded the best results in the kinetic resolution were subjected to a chemo-enzymatic sequence of deracemization. G. jasminoides immobilized cells in calcium alginate were used for the oxidation of the (S)-enantiomers and, in a second step, NaBH(4) was added to the same vessel for the reduction of the corresponding ketone. The sequential repetition of these two steps allowed obtaining the R-alcohols in 82-90% yield in high optical purity (71-96% ee). Despite the viability of the cells is affected by the chemical reagent, their enzymes remain active due to the protective environment of the calcium alginate beads.
authors.affiliation: INTEQUI-CONICET, Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, Chacabuco y Pedernera, CP 5700 San Luis, Argentina.
authors.forename: Cynthia
authors.initials: C
authors.lastname: Magallanes-Noguera
authors.forename: Mónica M
authors.initials: MM
authors.lastname: Ferrari
authors.forename: Marcela
authors.initials: M
authors.lastname: Kurina-Sanz
authors.forename: Alejandro A
authors.initials: AA
authors.lastname: Orden
mesh_terms: D002478:Cells, Cultured; D032062:Gardenia / Q000166:cytology* / Q000201:enzymology*; D010626:Phenylethyl Alcohol / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D010626:Phenylethyl Alcohol