Lipase-catalyzed kinetic resolution on solid-phase via a "capture and release" strategy

C E Humphrey, N J Turner, M A M Easson, S L Flitsch, R V Ulijn

Research output: Contribution to journalArticle

23 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)13952-13953
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number46
Early online date25 Oct 2003
DOIs
Publication statusPublished - 19 Nov 2003

Keywords

  • lipase-catalyzed kinetic resolution
  • solid-phase
  • capture and release strategy

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