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Lipase-catalyzed production of optically active acids via asymmetric hydrolysis of esters

Effect of the alcohol moiety

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Abstract

It has been found that lipase fromCandida cylindracea hydrolyzes octyl R(+)- but not S(-)-2-chloropropionate. At the same time, the enzyme exhibits no appreciable stereoselectivity in the hydrolysis of the methyl ester of the same acid. Solubility determination experiments showed that at the concentrations used, methyl 2-chloropropionate was completely dissolved in water, whereas the octyl ester existed as an emulsion in water. It is therefore speculated that in order to express its stereoselectivity the lipase needs to adsorb on the substrate—water interface.

R,S-2-chloropropionic acid was preparatively resolved via yeast lipase-catalyzed asymmetric hydrolysis of its octyl ester. Gram quantities of R(+)-chloropropionic acid and octyl S(-)-2-chloropropionate of high optical purity were readily prepared.

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Authors and Affiliations

  1. Laboratory of Applied Biochemistry, Department of Nutrition and Food Science, Massachusetts Institute of Technology, 02139, Cambridge, MA, USA

    Bernard Cambou & Alexander M. Klibanov

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  1. Bernard Cambou
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  2. Alexander M. Klibanov
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Cambou, B., Klibanov, A.M. Lipase-catalyzed production of optically active acids via asymmetric hydrolysis of esters. Appl Biochem Biotechnol 9, 255–260 (1984). https://doi.org/10.1007/BF02798491

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  • DOI: https://doi.org/10.1007/BF02798491

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