Lipase-catalyzed preparation of S-propranolol in presence of hydroxypropyl beta-cyclodextrins.
A simple method for the preparation of S-propranolol catalyzed by a Rhizopus niveus lipase in an aqueous medium is described. Hydroxypropyl-beta-cyclodextrin was used for the first time to increase the solubility of (R,S)-O-butyryl propranolol thus permitting the reaction to be carried out in water. The formation of an inclusion complex between (R,S)-O-butyryl propranolol and hydroxypropyl-beta-cyclodextrin was studied and a stoichiometry of 1:1 was determined. The influences of the hydroxypropyl-beta-cyclodextrin concentration, pH and percentage of ethanol on the enzymatic activity were also investigated. Under the conditions presented in this paper, values of ee(s) of 90% and E=48 were obtained.
Avila-González
Rizette
R
Departamento de Bioquímica y Biología Molecular-A, Facultad de Veterinaria, Universidad de Murcia, Campus de Espinardo, E-30100 Murcia, Spain.
Pérez-Gilabert
Manuela
M
García-Carmona
Francisco
F
D000073738:2-Hydroxypropyl-beta-cyclodextrin; D002384:Catalysis; D000431:Ethanol; D006863:Hydrogen-Ion Concentration; D007536:Isomerism; D008049:Lipase / Q000737:chemistry* / Q000378:metabolism; D011433:Propranolol / Q000378:metabolism*; D012233:Rhizopus / Q000201:enzymology*; D047392:beta-Cyclodextrins / Q000737:chemistry*
D047392:beta-Cyclodextrins; D000073738:2-Hydroxypropyl-beta-cyclodextrin; D000431:Ethanol; D011433:Propranolol; D008049:Lipase