Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 5, Issue 21, Pages 3456-3463Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b709716f
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Caffeine affects the stereoselectivity of microbial high cell density reductions with commercial grade Saccharomyces cerevisiae ( Baker's yeast). Cyclic beta-keto esters ethyl 2-oxocyclopentanoate ( 1) and ethyl 2-oxocyclohexanoate ( 3) were shown to be reduced with increased diastereoselectivity(1:90.1 -> 92.1% de, 3: 75.0 -> 90.0% de) after addition of caffeine. Effects on enantioselectivity were less pronounced ( 1: 97.3 -> 98.5% ee, 3: 90.1 -> 92.1% ee). The observations are ascribed to the action of caffeine on cellular calcium homeostasis. These effects are accompanied by caffeine-induced cell-death, which preferably takes effect on pre-stressed cells which were found to decrease diastereoselectivity.
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