• 제목/요약/키워드: Chiral epoxide

검색결과 42건 처리시간 0.023초

미생물 입체선택성 가수분해반응을 이용한 광학활성 1,2-epoxy-7-octene 생산을 위한 Hollow-fiber 반응기 시스템 개발 (Development of Hollow-fiber Reactor System for the Production of Chiral 1,2-epoxy-7-octene by Microbial Enantioselective Hydrolysis Reaction)

  • 이은열;김희숙
    • KSBB Journal
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    • 제16권3호
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    • pp.259-263
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    • 2001
  • The development of hollow fiber reactor system for the production of chiral 1,2-epoxy-7-octence by epoxide hydrolase for Rhodotorula glutinis was investigated. Dodecane with high solubility of the racemic substrate passed through the lumen side of the hollow fiber reactor and cell suspension was recirculated through the shell side. The 2nd hollow fiber reactor was coupled to the production reactor to extract the diol byproduct which was the inhibitor of epoxide hydrolase. Optically pure (S)-1,2-epoxy-7-octene (0.6 M in dodecane) could be obtained using hollow-fiber reactor system.

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A Stereoselective Asymmetric Synthesis of Antibiotic (-)-Fumagillol Using Claisen Rearrangement and Intramolecular Ester Enolate Alkylation as Key Steps

  • Kim Deukjoon;Ahn Soon Kil;Bae Hoon;Kim Hak Sung
    • Archives of Pharmacal Research
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    • 제28권2호
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    • pp.129-141
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    • 2005
  • (-)-Fumagillol (1), a hydrolysis product of fumagillin, has been synthesized by several group from commercially available 1,2:5,6-di-O-isopropylidene-${\alpha}$-D-allofuranose in a highly stereoselective manner. Chiral centers on C5 and C6 came from D-allofuranose and the asymmetric center on C4 was accomplished by 1,3-chirality transfer using the Claisen rearrangement on a chiral allyl alcohol. Chirality, which is necessary on an epoxide consisting of the spiro-ring system, was diastereoselectively constructed by the well-known reaction, intramolecular ester enolate alkylation (IEEA), which showed that this reaction can be applied to the alpha-alkoxy ester system. The epoxide on the side chain was regioselectively introduced by the difference between the number of substituents on the vinyl groups. This accomplishment proved that IEEA can be a useful tool for the synthesis of complex molecules.

Synthesis of New Bimetallic Chiral Salen Catalyst Bearing Co(BF4)2 Salt and Its Application in Asymmetric Ring Opening of Epoxide

  • Kim, Yong-Suk;Lee, Choong-Young;Kim, Geon-Joong
    • Bulletin of the Korean Chemical Society
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    • 제31권10호
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    • pp.2973-2979
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    • 2010
  • The newly synthesized homogeneous chiral Co(III) salen complexes were anchored non-covalently on the acidic sites of mesoporous Al-SBA-15. The Bronsted and Lewis acidic sites are attributed to the immobilization of fluorine functionalized chiral salen complexes on the supports. XRD, BET, TEM, FT-IR and ESCA (XPS) analyses were performed to characterize the property of support, and the structure of new homogeneous and heterogeneous chiral Co salen catalyst. The homogeneous and heterogeneous catalysts could be applied in asymmetric ring opening of epichlorohydrine (ECH) by water. They showed very high enantioselectivity and a good yield up to 99% in the catalytic synthesis of optically active products.

광학활성 Styrene Oxide 제조를 위한 고기능성 유전자 재조합 Epoxide Hydrolase 생촉매 개발

  • 이수정;이지원;이은정;김희숙;이은열
    • 한국생물공학회:학술대회논문집
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    • 한국생물공학회 2003년도 생물공학의 동향(XII)
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    • pp.435-438
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    • 2003
  • Epoxide hydrolase(EH) catalyze the enantioselective hydrolysis of racemic epoxides to corresponding diols. A recombinant Pichia pastoris with EH from Rhodotorula glutinis has been constructed by reverse transcriptase-polymerase chain reaction(RT-PCR). The recombinant biocatalyst enantioselectively hydrolyze (R)-styrene oxide faster than (S)-enantiomer. The catalytic activity of recombinant biocatalyst was 7-fold higher than that of wild-type strain. The recombinant EH biocatalyst can be used for kinetic resolution for the production of enantiopure styrene oxide.

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