title: Preparation of passion fruit-typical 2-alkyl ester enantiomers via lipase-catalyzed kinetic resolution.
abstract: The preparation of ester enantiomers (acetates, butanoates, hexanoates and octanoates) of the secondary alcohols 2-pentanol, 2-heptanol and 2-nonanol via lipase-catalyzed kinetic resolutions was investigated. Conversion rates and stereochemical courses of esterification and hydrolysis reactions catalyzed by commercially available enzyme preparations were followed for the homologous series of these passion fruit-typical 2-alkyl esters by capillary gas chromatography using heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-beta-cyclodextrin as chiral stationary phase. An efficient method was developed to prepare the ester enantiomers via lipase-catalyzed esterifications: optically pure (R)-2-alkyl esters (ee > 99.9%) were obtained by esterification of the racemic alcohols with enantioselective Candida antarctica lipase B (immobilized) as catalyst. The subsequent esterification of the unreacted alcohols using lipase from Candida cylindracea yielded the optically enriched (S)-esters (ee > 81.4%). The separation of the products via liquid solid chromatography using a mixture of silica gel and aluminum oxide (basic) resulted in high chemical purities and yields (> 40 mol %).
authors.affiliation: Lehrstuhl für Allgemeine Lebensmitteltechnologie, Technische Universität München, Maximus-von-Imhof-Forum 2, D-85350 Freising-Weihenstephan, Germany.
authors.forename: Hedwig
authors.initials: H
authors.lastname: Strohalm
authors.forename: Susanne
authors.initials: S
authors.lastname: Dold
authors.forename: Kathrin
authors.initials: K
authors.lastname: Pendzialek
authors.forename: Monika
authors.initials: M
authors.lastname: Weiher
authors.forename: Karl-Heinz
authors.initials: KH
authors.lastname: Engel
mesh_terms: D000438:Alcohols / Q000378:metabolism*; D002853:Chromatography, Liquid; D004800:Enzymes, Immobilized; D004951:Esterification; D004952:Esters / Q000378:metabolism*; D005232:Fatty Acids, Volatile / Q000378:metabolism; D005638:Fruit / Q000737:chemistry*; D005656:Fungal Proteins; D006868:Hydrolysis; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D029598:Passiflora / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D004800:Enzymes, Immobilized; D004952:Esters; D005232:Fatty Acids, Volatile; D005656:Fungal Proteins; D008049:Lipase; C431349:lipase B, Candida antarctica