Structural determinants defining common stereoselectivity of lipases toward secondary alcohols
M Cygler1, P Grochulski, J D Schrag
1Biotechnology Research Institute, National Research Council, Montréal, Canada.
Abstract:
In this review we summarize some aspects of the enantiopreference of the lipase from Candida rugosa following structural analysis of complexes of this lipase with two enantiomers of an analog of a tetrahedral intermediate in the hydrolysis of simple esters. The analysis of the molecular basis of the enantiomeric differentiation suggests that these results can be generalized to a large class of lipases and esterases. We also summarize our experiments on identification of the key regions in the lipases from Geotrichum candidum lipase responsible for differentiation between fatty acyl chains.
Related Concept Videos
E2 Reaction: Stereochemistry and Regiochemistry
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major product and...
E1 Reaction: Stereochemistry and Regiochemistry
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Regioselectivity of Electrophilic Additions-Peroxide Effect
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Conversion of Alcohols to Alkyl Halides


