Journal
CHIRALITY
Volume 20, Issue 5, Pages 724-735Publisher
WILEY
DOI: 10.1002/chir.20543
Keywords
kinetic resolution; lipases; secondary alcohol; absolute configuration; empirical rule; enantioselectivity
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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 similar to 50 secondary alcohols either as the only method or in combination with other methods.
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