Clay Column Chromatography for Optical Resolution: A Series of Derivatized Amino Acids

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  • Akihiko Yamagishi
    Faculty of Medicine, Toho University, Tokyo 143-8540 , Japan
  • Shohei Yamamoto
    Department of Chemistry, Graduate School of Science and Engineering, Ehime University, Matsuyama, Ehime 790-8577 , Japan
  • Kazuyoshi Takimoto
    Department of Chemistry, Graduate School of Science and Engineering, Ehime University, Matsuyama, Ehime 790-8577 , Japan
  • Kenji Tamura
    National Institute of Materials Science, Tsukuba, Ibaraki 305-0044 , Japan
  • Masumi Kamon
    National Institute of Materials Science, Tsukuba, Ibaraki 305-0044 , Japan
  • Fumi Sato
    Faculty of Medicine, Toho University, Tokyo 143-8540 , Japan
  • Hisako Sato
    Department of Chemistry, Graduate School of Science and Engineering, Ehime University, Matsuyama, Ehime 790-8577 , Japan

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<jats:title>Abstract</jats:title> <jats:p>Chromatographic resolution of a series of derivatized amino acids was attempted on a column packed with an ion-exchange adduct of Δ-[Ru(phen)3]2+ (phen = 1,10-phenanthroline) and synthetic hectorite. An amino acid was modified to N-3, 5-dinitrobenzoyl amino acid methyl ester (denoted by DNB-aa-me). For aa = Ala, Phe, Leu, Ile, Ser, Val, Thr, Tyr, Asp and Glu, racemic DNB-aa-me was resolved nearly to baseline separation on being eluted with methanol. For aa = Trp and His, racemic DNB-aa-me was resolved partially. No resolution was achieved for Pro and Lys. The mechanism of chiral discrimination was investigated by means of solid-state vibrational circular dichroism spectroscopy.</jats:p>

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