Catalytic and molecular properties of rabbit liver carboxylesterase acting on 1,8-cineole derivatives.
Nat Prod Commun
; 7(9): 1117-22, 2012 Sep.
Article
em En
| MEDLINE
| ID: mdl-23074884
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.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Cicloexanóis
/
Monoterpenos
/
Carboxilesterase
/
Biocatálise
/
Fígado
Limite:
Animals
Idioma:
En
Revista:
Nat Prod Commun
Assunto da revista:
BOTANICA
/
FARMACOLOGIA
/
QUIMICA
Ano de publicação:
2012
Tipo de documento:
Article
País de afiliação:
Argentina
País de publicação:
Estados Unidos