Synthesis of Enantiopure Propargylic Alcohols

4 Regioselective Reduction of t-Butyl 6-chloro-3,5-dioxohexanoate to the Corresponding Enantiopure (S)-S-Hydroxy Compound 

The reaction mixtures contained 5 and 0.5 mg of cells, respectively, in a total volume of 1 mL. To half the batches 1 mM NADP was added to check whether the amount of intracellular cofactor was sufficient to perform efficient reactions. Starting from 10 mM acetophenone, this ketone compound was completely reduced after a short reaction time by E. coli BL21(DE3)/pAW-3 and by E. coli BL21(DE3)/pAW-4 cells (0.5 mg of each) (Eig. 2.2.4.7). 

The specific cell activities for the reduction of 10 mM acetophenone, 15 mM 2,5-hexanedione, and 25 mM t-butyl 6-chloro-3,5-dioxohexanoate by E. coli BL21(DE3)/ pAW-3 and E. coli BL21(DE3)/pAW-4 are listed in Table 2.2.4.3, which shows that the reduction of acetophenone is the most efficient one, and that excellent specific cell activities were reached particularly with E. coli BL21(DE3)/pAW-3 cells. 

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