title: Enantioselective dynamic process reduction of α- and β-tetralone and stereoinversion of resulting alcohols in a selected strain culture.
abstract: α-Tetralone and β-tetralone were subjected to biotransformation by 14 fungal strains. Enantiomeric purity of the products depended on the reaction time. 3-Day transformation of α-tetralone in Absidia cylindrospora culture gave S-(+)-1,2,3,4-tetrahydro-1-naftol of 92 % ee, whereas longer biotransformation time resulted in decrease of ee value. 3-Day transformation of β-tetralone by the same strain gave predominantly S-(-)-1,2,3,4-tetrahydro-2-naftol, whereas after 9 days of the reaction, the R-enantiomer with 85 % ee was isolated. Transformation of β-tetralone by Chaetomium sp. KCh 6651 gave pure (S)-(-)-1,2,3,4-tetrahydro-2-naftol in high yield at the concentration of 1 g/l. In this process, a non-selective carbonyl reduction was observed, followed by a selective oxidation of the R-alcohol.
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Poland. janeczko13@interia.pl
authors.forename: Tomasz
authors.initials: T
authors.lastname: Janeczko
authors.forename: Anna
authors.initials: A
authors.lastname: Panek
authors.forename: Alina
authors.initials: A
authors.lastname: Swizdor
authors.forename: Jadwiga
authors.initials: J
authors.lastname: Dmochowska-Gładysz
authors.forename: Edyta
authors.initials: E
authors.lastname: Kostrzewa-Susłow
mesh_terms: D000438:Alcohols / Q000378:metabolism*; D001711:Biotransformation; D005658:Fungi / Q000378:metabolism*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D044024:Tetralones / Q000378:metabolism*; D013997:Time Factors
chemical_list: D000438:Alcohols; D044024:Tetralones