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  • Title: Determination of absolute configuration of secondary alcohols using lipase-catalyzed kinetic resolutions.
    Author: Jing Q, Kazlauskas RJ.
    Journal: Chirality; 2008 May 15; 20(5):724-35. PubMed ID: 18278808.
    Abstract:
    Lipases show high enantioselectivity toward a wide range of secondary alcohols. An empirical rule based on the relative sizes of the substituents predicts which enantiomer reacts faster. X-ray structures of lipases provide a molecular basis for this empirical rule: their alcohol-binding pocket contains large hydrophobic pocket open to solvent and another smaller pocket. This predictable enantiopreference of lipases allows the determination of the absolute configuration of secondary alcohols using lipase-catalyzed kinetic resolution. Researchers have used this relative method to determine the configuration of approximately 50 secondary alcohols either as the only method or in combination with other methods.
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