Optically active polyamides having (-)-anti head-to-head coumarin dimer component. 3. Chiral recognition ability.

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概要

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• Optically active polyamides (<B>3a–f</B>) and <I>O</I>-methylated polyamides (<B>5a</B>,<B>d</B>,<B>e</B>), derived from (−)-anti head-to-head coumarin dimer [(−)-<B>1</B>], were absorbed on macroporous silica gel particles and used as chiral stationary phases for direct resolution of racemates (<B>6–13</B>) having aromatic moiety by high-performance liquid chromatography. Polyamide <B>3a</B> and <B>3e</B> could resolve <B>6–10</B> and <B>9–13</B>, respectively (separation factor α>1.03), and <B>3d</B> showed especially high selective recognition ability to <B>7</B> (α=1.63). However, <B>3c</B>,<B>f</B> and <B>5a</B> showed no resolution ability to all of the racemates. The high recognition ability of <B>3a</B> is attributed mainly to the difference in stability between the diastereomeric complexes formed by the simultaneous interaction of <B>3a</B> with the racemates. The recognition ability of polyamides derived from piperazine (<B>3d</B>, <B>5d</B>) and 1,4-phenyl-enediamine (<B>3e</B>, <B>5e</B>) seems to be attributed not only to the simultaneous interaction but also to their ordered conformations in the film state.

• 公益社団法人 日本化学会の論文

著者

• Yonezawa Noriyuki

  Department Of Chemistry Gunma University

• Chen Yun

  Department Of Microbiology And Immunology Nanjing Medical University

• Hasegawa Masaki

  Department Of Materials Science And Technology Faculty Of Engineering Toin University Of Yokohama

• Tachibana Kouzou

  Department of Synthetic Chemistry, Faculty of Engineering, The University of Tokyo

• Saigo Kazuhiko

  Department of Applied Chemistry, Faculty of Engineering Saitama University

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