| Abstract
| - The enantioselective ring-opening catalyzed by epoxide hydrolases originating from seven different sourcesof a series of 2,2-disubstituted oxiranes containing alkyl chains of different lengths, unsaturated (alkenyl,alkinyl) and aromatic groups as well as electronegative heteroatoms at various positions within the sidechain was analyzed by quantitative structure−activity relationships. Models for the enantioselectivity werederived with the aid of multiple linear regression analysis (MLR) using several steric and electronic (quantumchemical) descriptors. On the basis of the models derived by MLR nonlinear modeling with artificial neuralnetworks (ANN) was also done. Good predictive performance was observed for both modeling approaches.The models also indicate that different steric and/or electronic features account for the enantioselectivitiesobserved for the individual epoxide hydrolases.
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