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KMID : 1059519920360010125
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Journal of the Korean Chemical Society
1992 Volume.36 No. 1 p.125 ~ p.130
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Synthesis of Stereoisomeric Trifluoroethylmandelates and Their Stereospecificity for the Uses as the Substrate of Lipases in Organic Solvent
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Kwon Dae-Young
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Abstract
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Stereoisomers of trifluoroethylmandelate(mandelic acid trifluoroethylester) were synthesized from each isomer of mandelic acid and trifluoroethanol with p-toluene sulfonic acid in order to study the enantioselectivity of lipase in organic solvent. The products were identified by 1H NMR and elemental analysis and their physical properties such as melting point, densities and specific optical rotations([α]25D) were also characterized. [α]25D of (+)- and (-)-trifluoroethylmandelate were +74° and -75.4°, respectively. The trifluoroethylmandelate was found out to be as a good substrate for the transesterfication stereoselectivity of lipases in organic solvent. Any significant difference of the lipase catalyzed transesterification activity between (+)- and (-)-methylchloropropionate was not found, and even lipase activity of transesterfication was not found with high optical polar (+)-and (-)-methylmandelate.
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KEYWORD
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