Abstract

By lipase-catalyzed stereoselective transesterification using Amano AK from Pseudomonas sp., nitroalcohols such as 1-nitro-2-butanol and 1-nitro-3-methyl-2-butanol were synthesized enantioselectively with enantiomeric ratios ( E values) of 20.9 and 12.5, respectively, in n-propyl ether. Various results were obtained during the lipase-catalyzed transesterification by changing the organic solvents that were used. The plots of the E values against the reciprocal of the dielectric constants ( ε) of the various organic solvents produced a bell-shaped curve which had a maximum E value for n-propyl ether (1/ ε=0.3). The distance between the enzyme and the substrate might be changed in response to a change in the organic solvent.

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