• Title/Summary/Keyword: Asymmetric reaction

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Studies Directed Toward Asymmetric Total Synthesis of Calycotomine (Calycotomine의 입체선택적 합성 연구)

  • Yang, Jung-Eun;Jung, Jae-Kyung
    • YAKHAK HOEJI
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    • v.53 no.3
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    • pp.161-164
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    • 2009
  • Synthetic studies directed toward an asymmetric total synthesis of calycotomine, an representative tetrahydroisoquinoline, are described. The application of N-tert-butane sulfinyl chiral auxiliary to the Pictet-Spengler type reaction for the efficient synthesis of tetrahydroisoquinoline skeleton has been also investigated.

Optimization of Batch Production of Chiral Phenyl Oxirane by Response Surface Analysis (반응표면분석법을 이용한 광학활성 phenyl oxirane의 회분식생산 최적화)

  • 김희숙;박성훈;이은열
    • Journal of Life Science
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    • v.13 no.6
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    • pp.794-798
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    • 2003
  • Batch production of (S)-phenyl oxirane was investigated using epoxide hydrolase activity of Rhodosporidium toruloides SJ-4. Effect of reaction condition of asymmetric biohydrolysis of racemic phenyl oxirane was analyzed and optimized by response surface methodology. The optimal conditions of pH, temperature and DMSO cosolvent ratio were 7.4, $34^P\circ}C$, and 2.3%(v/v), respectively. The final yield was enhanced up to 67%, and reaction times required to reach 99% ee (enatiomeric excess) decreased down to 50% by response surface methodology Enantiopure (S)-phenyl oxirane with 100% enantiopurity and 24% yield (theoretical yield = 50%) was obtained from racemic substrate.

Asymmetric Michael Reaction of Malonate Derivatives with α, β-Unsaturated Ketones

  • Cho, Min-Je;Cho, Myoung-Gi;Huh, Sun-Chul;Kim, Sung-Min;Lee, Kil-sung;Koh, Kwang-Oh;Mang, Joo-Yang;Kim, Dae-Young
    • Bulletin of the Korean Chemical Society
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    • v.27 no.6
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    • pp.857-862
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    • 2006
  • The catalytic enantioselective Michael reaction promoted by quaternary ammonium salts from Cinchona alkaloids as a phase-transfer catalyst is described. Treatment of malonates with $\alpha$,$\beta$-unsaturated ketones under mild reaction conditions afforded the corresponding Michael adducts in good yields with good to moderate enantiomeric excesses.

Asymmetric Sythesis of Unnatural L-Amino Acids Using Thermophilic Aromatic L-Amino Acid Transaminase

  • Cho, Byung-Kwan;Seo, Joo-Hyun;Kim, Ju-Han;Lee, Chang-Soo;Kim, Byung-Gee
    • Biotechnology and Bioprocess Engineering:BBE
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    • v.11 no.4
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    • pp.299-305
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    • 2006
  • Aromatic L-amino acid transaminase is an enzyme that is able to transfer the amino group from L-glutamate to unnatural aromatic ${\alpha}-keto$ acids to generate ${\alpha}-ketoglutarate$ and unnatural aromatic L-amino acids, respectively. Enrichment culture was used to isolate thermophilic Bacillus sp. T30 expressing this enzyme for use in the synthesis of unnatural L-amino acids. The asymmetric syntheses of L-homophenylalanine and L-phenylglycine resulted in conversion yields of >95% and >93% from 150 mM 2-oxo-4-phenylbutyrate and phenylglyoxylate, respectively, using L-glutamate as an amino donor at $60^{\circ}C$. Synthesized L-homophenylalanine and L-phenylglycine were optically pure (>99% enantiomeric excess) and continuously pre-cipitated in the reaction solution due to their low solubility at the given reaction pH. While the solubility of the ${\alpha}-keto$ acid substrates is dependent on temperature, the solubility of the unnatural L-amino acid products is dependent on the reaction pH. As the solubility difference between substrate and product at the given reaction pH is therefore larger at higher temperature, the thermophilic transaminase was successfully used to shift the reaction equilibrium toward rapid product formation.

Asymmetric Polymerase Chain Reaction-Single-Strand Conformation Polymorphism (Asymmetric PCR-SSCP) as a Simple Method for Allele Typing of HLA-DRB

  • Kang, Joo-Hyun;Kim, Kyeong-Hee;Maeng, Cheol-Young;Kim, Kil-Lyong
    • BMB Reports
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    • v.32 no.6
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    • pp.529-534
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    • 1999
  • Asymmetric PCR and single-strand conformation polymorphism (SSCP) methods were combined to analyze human leukocyte antigen (HLA)-DRB allele polymorphism. Asymmetric PCR amplification was applied to generate single-stranded DNA (ssDNA) using the nonradioactive oligonucleotide primers desinged for the polymorphic exon 2 region. The conformational differences of ssDNAs, depending on the allele type, were analyzed by nondenaturing polyacrylamide gel electrophoresis and visualized by ethidium bromide staining. The ssDNAs were clearly separated from double-stranded DNA without interference and obviously migrated depending on their allele type. This method was applied to the genomic DNA either from homozygous or from heterozygous cell lines containing the DR4 allele as template DNA using DR4-specific primers, and satisfying results were obtained. Compared to the standard PCR-SSCP method, this asymmetric PCR-SSCP method has advantages of increased speed, reproducibility, and convenience. Along with PCR-SSP or sequence-based typing, this method will be useful in routine typing of HLA-DRB allele.

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