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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 36, Number 1
JKCSEZ 36(1)
February 20, 1992 

 
Title
Synthesis of Stereoisomeric Trifluoroethylmandelates and Their Stereospecificity for the Uses as the Substrate of Lipases in Organic Solvent

유기용매내에서 리파제의 입체특이성 반응기질로서 이용하기 위한 Trifluoroethylmandelate의 이성질체 합성 및 입체특이성
Author
Dae Young Kwon

권대영
Keywords
Abstract
유기용매에서 리파제의 입체특이성 반응연구를 위하여 리파제의 기질로서 trifluoroethylmandelate를 도안하고 이를 mandelic acid와 trifluoroethanol를 사용하여 알코올과 산에서 에스텔을 합성하는 방법을 도입하여 합성하였다. 합성된 물질이trifluoroethylmandelate임을 1H NMR과 원소 분석을 통하여 확인하였다. (+)- 와 (-)-trifluoroethylmandelate ([α]25D)은 각각 +74.0°and -75.4°이었다. 이 합성된 기질을 이용하여 유기용매내에서의 리파제의 입체이성질체에 대한 transesterification 속도는 서로간에 상당한 차이가 나타났다. 반면에 [α]25D가 낮은 입체 이성질체인 (+)- 와 (-)-methylchloropropionate에서는 리파제의 활성은 있었으나 차이는 없었으며, 높은 [α]25D를 갖는 methylmadelate는 리파제의 활성도 없었다.

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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125 - 130
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