Abstract
A selection of bacteria, fungi and yeasts known to achieve ketone reduction reactions were assessed for their abilities to transform enantiomeric 2-oxo-1,4-cineoles to their respective alcohol products. Microbiological reduction of the (−)- ketone isomer led to the formation of a preponderance of the corresponding endo-alcohol isomer with all organisms, indicating that ‘re’-face reductase specificity predominates. The (+)- ketone isomer gave mixed results. Curvularia lunata formed a preponderance of the endo-alcohol isomer, indicating the presence of ‘si’-face specific reductases in this organism, while Penicillium frequentans gave a higher proportion of the exo-alcohol isomer, indicating the presence of ‘re’-face specific reductases. Kinetic studies showed that constant ratios of exo/endo-alcohol products were obtained when (+)- 2-'oxo-1,4-cineole is reduced by C. lunata, but that the ratios of alcohol isomers changed with time when reductions were catalyzed by P. frequentans.
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