MINOR SYNTHETIC CAPACITIES OF BAKERS-YEAST TOWARDS UNNATURAL SUBSTRATES

Baker's yeast catalyzes numerous transformations on reactive substrates. alpha, beta-Unsaturated aldehydes undergo water addition with the formation of chiral secondary alcohols, but sulfur nucleophiles (mercaptans) chemically add to the double bond with partial kinetic resolution observed in the secondary thiol obtained, following enantioselective reduction of the intermediate aldehydes. These sulfur nucleophiles however interact with the yeast metabolic pathway allowing the isolation of carbohydrate derived chiral intermediates. The use of deuterated precursors or performing the fermentation in D2O allows the isolation of chiral glycerol derivatives stereoselectively deuterated at different positions.