Determination of absolute configuration of secondary alcohols using lipase-catalyzed kinetic resolutions

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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 ∼50 secondary alcohols either as the only method or in combination with other methods.

Original languageEnglish (US)
Pages (from-to)724-735
Number of pages12
JournalChirality
Volume20
Issue number5
DOIs
StatePublished - May 15 2008

Keywords

  • Absolute configuration
  • Empirical rule
  • Enantioselectivity
  • Kinetic resolution
  • Lipases
  • Secondary alcohol

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