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Catalytic and molecular properties of rabbit liver carboxylesterase acting on 1,8-cineole derivatives.

Natural product communications (2012-10-19)
María H del Loandos, Ana C Muro, Margarita B Villecco, Marcelo F Masman, Paul G M Luiten, Sebastian A Andujar, Fernando D Suvirec, Ricardo D Enriz
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Eucalyptol, 99%
Supelco
Eucalyptol, analytical standard
Sigma-Aldrich
Eucalyptol, natural, ≥99%, FCC, FG
Supelco
1,8-Cineole, primary reference standard
Cineole, European Pharmacopoeia (EP) Reference Standard
Sigma-Aldrich
Esterase from rabbit liver, lyophilized powder, ≥30 units/mg protein
Supelco
Eucalyptol, certified reference material, TraceCERT®