New yeast strains for enantioselective production of halohydrin precursor of (S)-Propranolol

The synthesis of (R) or (S) 1-chloro-3-(1-naphthyloxy)propan-2-ol, (2-Propranolol precursor) using yeast-catalysed reduction of 1-chloro-3-(1-naphthyloxy)propan-2-one, 1 is described. Several yeast strains have been used. The best strains were selected using the reduction of cyclohexanone, as the reaction test. These selected strains were more active and productive than the commercial strain of S. cerevisiae from Sigma. The stereoselective reduction of 1 was performed using actively fermenting cells or fresh resting cells. The last experimental conditions were the best to achieve good yields and e.e. in 1. Pichia mexicana 11015 resting cells gave 85% yield in (R) 1 (e.e. = 95%) (precursor of (S)-Propranolol). Yarrowia lipolytica 1240 resting cells gave 87% yield in (S) 1 (e.e. = 99%).