• Title/Summary/Keyword: Ketoproline

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Asymmetric Reduction of 3-Ketoproline Ethyl Ester by Modified Borohydrides and Various Vegetables

  • Wibowo, Agustono;Shaameri, Zurina;Mohammat, Mohd Fazli;Hamzah, Ahmad Sazali
    • Journal of the Korean Chemical Society
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    • v.61 no.5
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    • pp.244-250
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    • 2017
  • Reduction of (${\pm}$)-3-ketoproline ethyl ester (1) by $NaBH_4$ in the presence of $CaCl_2$ and $MgCl_2$ as the chelating agents gave selective products cis-3(R/S)-alcohols, while reduction by $NaBH_4$ alone or chelated with $NiCl_2$ and $AlBr_3$ gave mixtures of cis- and trans-alcohols. The reduction of (${\pm}$)-1 by various vegetables however, gave exclusively the cis-alcohol as the major and trans-alcohol as the minor. On the contrary, reduction of (${\pm}$)-1 by carrot afforded a mixture of cis- and trans-alcohols, in which the trans-alcohol exists as the major product. In addition, we found that this biocatalyst selectively converted S-enantiomer of (${\pm}$)-1 to the cis-alcohol, and R-enantiomer to a mixture of cis- and trans-alcohols with cis-alcohol as the major product. This fact prompted us to use various fresh plant tissues for stereoselective reduction of diverse types of pyrrolidinones, as its stereoselectivity towards racemic mixtures is higher compared to that using chemical reducing agents.

Characteristics of Antitumor Antibiotics HS-1 from a Stveptomyces JIoridiae SHS-1372 (Streptomyces floridae SHS-1372가 생산하는 항암항생물질 HS-1의 특성)

  • 하상철;홍순덕
    • Microbiology and Biotechnology Letters
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    • v.22 no.2
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    • pp.169-174
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    • 1994
  • Antitumor antibiotic HS-1 was purified from the culture broth of a streptomyces floridae SHS-1372 which had been isolated from soil, by solvent extraction, silica gel column chromatography and gel filtration. It was confirmed that HS-1 was active against gram positive bacteria and cancer cells(K562, P388, MCF-7, HT-29). Through the analysis of UV spectrum, melting point, IR spectrum, FAB-MS, $_{1}$H-NMR, $_{13}$C-NMR, 2D-NMR spectra, HS-1 could be identified sa the actinomycin X$_{2}$ antibiotics containing actinocine chromophore and peptides consisted of threonine, proline, methylvaline, sarcosine, D-valine and 4-ketoproline.

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