高等学校化学学报 ›› 2000, Vol. 21 ›› Issue (2): 249.

• 研究简报 • 上一篇    下一篇

超分子体系中的分子识别研究(一)——有机硒修饰β-环糊精的合成及其与L-和D-色氨酸的包结配位作用

尤长城, 刘育   

  1. 南开大学化学系, 天津 300071
  • 收稿日期:1999-05-18 出版日期:2000-02-24 发布日期:2000-02-24
  • 通讯作者: 刘 育(1954年出生),男,博士,教授,主要从事超分子化学研究.
  • 基金资助:

    国家杰出青年科学基金(批准号:29625203);天津市自然科学基金(批准号:29672021和973602211)资助

Mpolecular Rexognigion Studies on Supram olecular Systems(ⅩⅩⅩ)——Syntheses of Organoselenium Modified β-Cyclodextrins and Their Inclusion Complexation with L- and D-Tryptophan

YOU Chang-Cheng, LIU Yu   

  1. Department of Chemistry, Nankai University, Tianjin 300071, China
  • Received:1999-05-18 Online:2000-02-24 Published:2000-02-24

关键词: 修饰环糊精, 超分子配合物, 手性识别, 色氨酸

Abstract: Mono(2-phenylseleno-2-deoxy)-β-cyclodextrin(2) and mono[2-(p-methoxyphenylseleno)-2-deoxy]-β-cyclodextrin(4), were newly synthesized and characterized by combustion analyses, IR, 1H NMRand 13C NMR. Spectrofluorometric titrations have been performed in aqueous phosphate buffer solution(pH7.20, 0.1 mol/L) at 25 ℃ to give the complex KSand -ΔG° for the stoichiometric 1∶1 inclusion complexation of mono(6-phenylseleno-6-deoxy)-β-cyclodextrin(1), mono[6-(p-methoxyphenylseleno)-6-deoxy]-β-cyclodextrin(3) and the novel cyclodextrin derivatives 2 and 4 with L- and D-tryptophan. The molecular binding ability and selectivity for L- and D-tryptophan of modified β-cyclodextrins(1_4) are discussed from the size/shape-fit and geometrical complement relationships between the host cavity and the guest molecule. The results obtained indicate that van der Waals force and hydrophobic interactions dominate the complexation of 1-4 and the aromatic substituents introduced extend the original hydrophobicity of cavity and the molecular binding ability, but reduce the enantioselectivity for L/D-tryptophan guests.

Key words: Modified cyclodextrin, Supramolecular complex, Chiral recognition, Tryptophan

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