• Title/Summary/Keyword: enantioselective

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Enantioselective Resolution for the Preparation of Chiral para-Nitrostyrene Oxide by Microbial Epoxide Hydrolase in an Organic Solvent (미생물 에폭사이드 가수분해효소 활성을 이용한 유기용매에서의 광학활성 para-Nitrostyrene Oxide 생산)

  • 배현철;김현숙;이수정;이은열;양승택;김희숙
    • Journal of Life Science
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    • v.12 no.4
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    • pp.423-426
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    • 2002

  • Enantioselective resolution of racemic para-nitrostyrene oxide was investigated using epoxide hydrolase activity of Aspergillus niger LK for the production of optically pure (S)-para-nitrostyrene oxide. To overcome the poor solubility of the substrate, enantioselective hydrolysis in an organic solvent was attempted under optimized reaction conditions including reaction temperature and water content. (S)-para-Nitrostyrene oxide with high optical purity (> 99% ee) was obtained at 37% yield using fungal epoxide hydrolase-catalyzed enantioselective resolution.

  • https://doi.org/10.5352/JLS.2002.12.4.423 인용 PDF KSCI

Molecular Cloning and Functional Expression of esf Gene Encoding Enantioselective Lipase from Serratia marcescens ES-2 for Kinetic Resolution of Optically Active (S)-Flurbiprofen

  • Lee, Kwang-Woo;Bae, Hyun-Ae;Lee, Yong-Hyun
    • Journal of Microbiology and Biotechnology
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    • v.17 no.1
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    • pp.74-80
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    • 2007

  • An enantioselective lipase gene (esf) for the kinetic resolution of optically active (S)-flurbiprofen was cloned from the new strain Serratia marcescens ES-2. The esf gene was composed of a 1,845-bp open reading frame encoding 614 amino acid residues with a calculated molecular mass of 64,978 Da. The lipase expressed in E. coli was purified by a three-step procedure, and it showed preferential substrate specificity toward the medium-chain-length fatty acids. The esf gene encoding the enantioselective lipase was reintroduced into the parent strain S. marcescens ES-2 for secretory overexpression. The transformant S. marcescens BESF secreted up to 217kU/ml of the enantioselective lipase, about 54-fold more than the parent strain, after supplementing 3.0% Triton X-207. The kinetic resolution of (S)-flurbiprofen was carried out even at an extremely high (R,S)-flurbiprofen ethyl ester [(R,S)-FEE] concentration of 500 mM, 130 kU of the S. marcescens ES-2 lipase per mmol of (R,S)-FEE, and 1,000 mM of succinyl ${\beta}-cyclodextrin$ as the dispenser at $37^{\circ}C$ for 12h, achieving the high enantiomeric excess and conversion yield of 98% and 48%, respectively.

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Biocatalytic Preparation of Chiral Epichlorohydrins Using Recombinant Pichia pastoris Expressing Epoxide Hydrolase of Rhodotorula glutinis

  • Kim, Hee-Sook;Lee, Jae-Hwa;Park, Sunghoon;Lee, Eun-Yeol
    • Biotechnology and Bioprocess Engineering:BBE
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    • v.9 no.1
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    • pp.62-64
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    • 2004

  • The use of enantioselective hydrolysis for preparing chiral epichlorohydrins was investigated using recombinant Pichia pastoris with the enantioselective epoxide hydrolase of Rhodotorula glutinis. The rate of the recombinant epoxide hydrolase-catalyzed enantioselective hydrolysis of racemic epichlorohydrins was enhanced by the addition of 5%(v/v) Tween 20. Enantiopure (R)-epichlorohydrins with an enantiopurity of 100% ee and a yield of 26% were obtained within 5min from 50mM racemates.

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