Aromatic Foldamers Recognizing Saccharides to Form Chiral Helices

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  • Abe Hajime
    Graduate School of Pharmaceutical Sciences, University of Toyama

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  • 糖質の認識によりキラルならせんを巻く芳香族フォルダマー
  • Symposium Review 糖質の認識によりキラルならせんを巻く芳香族フォルダマー
  • Symposium Review トウシツ ノ ニンシキ ニ ヨリ キラル ナ ラセン オ マク ホウコウゾク フォルダマー

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Abstract

<p>New meta-arylene ethynylene foldamers were developed by employing pyridine and phenol units. These demonstrated interesting properties related to the hydrogen-bonding behavior of the arylene units. Pyridine-acetylene-phenol foldamers showed improved saccharide recognition abilities compared with pyridine-acetylene foldamers with no phenol units. Solid-liquid extraction could be achieved due to the strong binding. Hydrocarbon stapling by alkene metathesis under templation was attempted, and the helical structure was efficiently stabilized. Phenol-acetylene oligomers spontaneously formed helical structures via intramolecular hydrogen bonding. The helical sense could be biased by adding chiral amines.</p>

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 139 (4), 591-598, 2019-04-01

    The Pharmaceutical Society of Japan

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