Tarcila Cazetta, P. J. Moran, J. A. Rodrigues
Nov 1, 2014
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Influential Citations
14
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Journal
Journal of Molecular Catalysis B-enzymatic
Abstract
Abstract A very simple methodology was developed to transform racemic 1-(4-substitutedphenyl)-1,2-ethanediols using resting cells of Candida albicans CCT 0776 through a one-pot two-step process in which the ( R )-stereoisomer was completely oxidized to the corresponding substituted-α-hydroxyacetophenones, which were completely reduced to produce ( S )-1-(4-substitutedphenyl)-1,2-ethanediols in good isolated yield (60–85%) and with high enantiomeric excess (99% ee). The overall process corresponded to an enantioselective deracemization by stereoinversion of the ( R )-enantiomer. The process was not achieved for other similar 1,2-diols using the same reaction conditions, which indicates a structural restriction of substrates by the active pocket of the enzymes of C. albicans involved in the stereoinversion process.