title: Lipase-catalyzed kinetic resolution on solid-phase via a "capture and release" strategy.
abstract: The lipase-catalyzed kinetic resolution of (R/S)-3-phenylbutyric acid 2 using solid-supported cyclohexane-1,3-dione (CHD) 6 is described. In each case the predominant enantiomer observed, after cleavage from the resin, was (R)-(-)-3-phenylbutyric acid (R)-2 (ee > 99%) rather than the expected (S)-enantiomer of 2. This observation is in contrast to the fact that Chromobacterium viscosum lipase shows high enantiospecificity for the (S)-enantiomer in the corresponding solution-phase hydrolysis reactions. The (R)-acyl group was subsequently released from the resin by NaOH hydrolysis, and the yield of the reaction could be improved by triple acylation of the resin.
authors: School of Chemistry, University of Edinburgh, King's Buildings, West Mains Road, Edinburgh, Scotland, UK.
authors: Cara E
authors: CE
authors: Humphrey
authors: Nicholas J
authors: NJ
authors: Turner
authors: Morag A M
authors: MA
authors: Easson
authors: Sabine L
authors: SL
authors: Flitsch
authors: Rein V
authors: RV
authors: Ulijn
mesh_terms: D000215:Acylation; D002264:Carboxylic Acids / Q000737:chemistry / Q000302:isolation & purification*; D002384:Catalysis; D004952:Esters / Q000737:chemistry / Q000302:isolation & purification*; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D011092:Polyethylene Glycols / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D002264:Carboxylic Acids; D004952:Esters; C109511:bis(polyoxyethylene bis(amine)); D011092:Polyethylene Glycols; D008049:Lipase; C454481:lipase, Chromobacterium viscosum