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KMID : 0380020040190030215
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Korean Journal of Biotechnology and Bioengineering
2004 Volume.19 No. 3 p.215 ~ p.220
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Solid Bases as Racemization Catalyst for Lipase-catalyzed Dynamic Kinetic Resolution of Naproxen 2,2,2-Trifluoroethyl Thioester
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Kim Sang-Bum
Won Ki-Hoon
Moon Sang-Jin
Kim Kwang-Je
Park Hong-woo
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Abstract
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A variety of solid bases such as inorganic bases, basic anion exchange resins, and resin-bound bases were tested as a catalyst for racemization of (S)-naproxen 2,2,2-trifluoroethyl thioester in isooctane at 45. Among the various bases, DIAIOM WA30, which is a weakly basic anion exchange resin with a tertiary amine based on a highly porous type styrene-divinylbenzene copolymer, showed the highest catalytic activity. The second-order interconversion constant of DIAION WA30 was 8.610-4/ mM-1/h-1/ and about 3 times higher than that of trioctylamine under the same conditions. The rate of DIAION WA30-catalyzed racemization decreased with increasing an amount of water added to the reaction medium. Lipase-catalyzed kinetic resolution of racemic naproxen 2,2,2-trifluoroethyl thioester was successfully carried out under in situ racemization of substrate with DIAION WA30 in isooctane at 45. More than 60% conversion and 99% enantiomeric excess for the desired (S)-naproxen product were obtained. Furthermore, such a solid base catalyst could be easily separated and reused in contrast to trioctylamine.
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KEYWORD
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Dynamic kinetic resolution, lipase, naproxen, solid base, racemization
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