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Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus
Authors:Marlene Espinoza-Moraga  Tania Petta  Marco Vasquez-Vasquez  V Felipe Laurie  Luis AB Moraes  Leonardo Silva Santos
Institution:1. Laboratory of Asymmetric Synthesis, Talca University, Talca PO Box 747, Chile;2. Faculdade de Ciencias, Universidade de Sao Paulo, Ribeirao Preto 14040-901, Brazil;3. Facultad de Ciencias Agrarias, Talca University, Talca PO Box 747, Chile
Abstract:β-Carboline imine reductions mediated by Saccharomyces bayanus have been described achieving moderate to good enantiomeric excesses of the amine products. The enantiomeric excesses of the bioreduction showed a dependence on the imine substituents. Compounds presenting C1–C11 aliphatic substituent groups afforded amines with an (S)-configuration, whereas C15 and higher aliphatic- and aromatic-substituted β-carboline imines achieved inversion of the configuration in the final (R)-2 amine products. Based on this data, a model for the Saccharomyces reduction is proposed.
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