ENZYMES IN ORGANIC-SYNTHESIS .47. ACTIVE-SITE MODEL FOR INTERPRETING AND PREDICTING THE SPECIFICITY OF PIG-LIVER ESTERASE

Pig liver esterase (PLE) is one of the most useful enzymes for the preparation of valuable chiral synthons. However, its applications in asymmetric synthesis have been hampered by its seemingly unpredictable specificity. This disadvantage has now been overcome through the development of a simple and easy-to-use active-site model. The model, which is based on cubic-space descriptors, accounts for the structural selectivity and stereoselectivity of PLE-catalyzed hydrolyses reported so far and is also of predictive value for new substrate structures. The development and specification of the model, and its application in analyzing the specificity of the enzyme toward a representative and structurally diverse range of methyl ester substrates, are described. © 1990, American Chemical Society. All rights reserved.