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

Humphrey, C E and Turner, N J and Easson, M A M and Flitsch, S L and Ulijn, R V (2003) Lipase-catalyzed kinetic resolution on solid-phase via a "capture and release" strategy. Journal of the American Chemical Society, 125 (46). pp. 13952-13953. ISSN 1520-5126 (https://doi.org/10.1021/ja037922x)

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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.

ORCID iDs

Humphrey, C E, Turner, N J, Easson, M A M, Flitsch, S L and Ulijn, R V ORCID logoORCID: https://orcid.org/0000-0001-7974-3779;
  • Item type:Article
    ID code:43943
    Dates:
    Date
    Event
    19 November 2003
    Published
    25 October 2003
    Published Online
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:30 May 2013 11:34
    Last modified:11 Nov 2024 10:25
    URI:https://strathprints.strath.ac.uk/id/eprint/43943
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