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Reduction and cyclization in biotransformation of carbonyl compounds by cultured cells of Taxus species
Authors:Consuelo Sandoval  José M. Méndez  Rubén Sánchez-Obregón  Carmen B. Alpízar
Affiliation:1. Departamento de Química Orgánica, Facultad de Química;2. Departamento de Síntesis Orgánica, Instituto de Química;3. Instituto de Química, Departamento de Bioquímica, Universidad Nacional Autónoma de México, México
Abstract:
Cultured plant cells from Taxus brevifolia Nutt and Taxus globosa Schltdl were investigated as biocatalysts using exogenous substrates. Production of highly specific metabolites by these species prompted us to analyse their synthetic potential. Whole cells suspensions have the capacity to chemoselectively reduce ethyl acetoacetate to ethyl 3-hydroxybutyrate chemo- and stereoselectively reduce rac-2-benzoylcyclohexanone to (1R, 2S)- and (1S, 2S)-2-hydroxycyclohexylphenylmethanones, and to cyclize N-phthaloyl-L-glutamine to thalidomide.
Keywords:Taxus brevifolia  Taxus globosa  cell cultures  bioreduction  biocyclization  ethyl acetoacetate  2-benzoylcyclohexanone  N-phthaloyl-L-glutamine  thalidomide
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