Preparation of (1R )[1—2H]- and (1S)[1—2H]-Alcohols by Exchange Reactions Catalyzed by Yeast or a Coupled Enzyme System

All possible enantiomers of stereospecifically labelled [1-2H] ethanol, propanol and butanol have been prepared on a scale of up to 7 ml. The R forms have been obtained by incubation of the alcohols with alcohol dehydrogenase and diaphorase (NAD: Lipoamide oxidoreductase, EC 1.6.4.3) in presence of catalytic amounts of NAD+/NADH in deuterium oxide. The S forms have been prepared with the same enzymes in ordinary water, from the corresponding [1,1-2H] alcohols. (IS) [1-2H] ethanol was prepared from [1,1-2H] ethanol and ordinary water, by a yeast catalyzed exchange reaction.