del Loandos_2012_Nat.Prod.Commun_7_1117

Rabbit liver carboxylesterase rCE was evaluated as the catalyst for the enantioselective hydrolysis of 3-endo-acetyloxy-1 8-cineole 4 which yields 1S,3S,4R)-(+)-3-acetyloxy-1,8-cineole 4 and 1R,3R,4S)-(-)-3-hydroxy-1,8-cineole 3 Enantioselective asymmetrization of meso-3,5-diacetoxy-1,8-cineol 5 gives 1S,3S,4R,5R)-(-)-3-acetyloxy-5-hydroxy-1,8-cineole 6 with high enantioselectivity rCE has been chosen to perform both experiments and molecular modeling simulations Docking simulations combined with molecular dynamics calculations were used to study rCE-catalyzed enantioselective hydrolysis of cineol derivatives Both compounds were found to bind with their acetyl groups stabilized by hydrogen bond interactions between their oxygen atoms and Ser221.