Abstract
Stereoselective esterification of(R, S) 2-octanol with octanoic acid catalyzed byCandida Sp lipase (CSL) was carried out in cyclohexane. We have studied the effects of factors, such as temperature and the microenvironment of lipase, on this reaction. The results showed that CSL favoredR enantiomer of(R, S) 2-octanol, and that the esterification activity and stereoselectivity of the lipase were dependent on these factors. The higher the temperature, the greater the esterification activity of CSL. A slight increase in stereoselectivity can be seen with temperature decrease. The optimal range of pH value for this reaction was 4.9–6.2. When the salt concentration was between 0 and 0.05 mol/L, CSL showed high activity. The salt concentration in the reaction system and the pH value at which CSL powder was prepared from the aqueous solution had no evident effect on the stereoselectivity of CSL.
The optimal range of the water content in the reaction system was 0.4–1.6%. The esterification activity and the stereoselectivity of CSL were enhanced 1.4-fold and 2.0-fold, respectively, by immediately removing the produced water. (S) 2-octanol with 95.2% enantiomeric excess (ee) was prepared. Based on these results, we have discussed why that all these factors affected this reaction.
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Yang, H., Cao, S.G., Han, S.P. et al. Studies on the factors that affect stereoselective esterification of (R, S) 2-octanol with octanoic acid catalyzed by lipase in organic solvent. Appl Biochem Biotechnol 59, 177–186 (1996). https://doi.org/10.1007/BF02787819
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DOI: https://doi.org/10.1007/BF02787819