Surface Active Crown Ethers. XI.

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  • INOKUMA Seiichi
    Department of Synthetic Chemistry, Faculty of Technology, Gunma University
  • IRISAWA Yutaka
    Department of Synthetic Chemistry, Faculty of Technology, Gunma University
  • KUWAMURA Tsunehiko
    Department of Synthetic Chemistry, Faculty of Technology, Gunma University

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Other Title
  • 界面活性クラウンエーテル(第11報)
  • カイメン カッセイ クラウンエーテル 11 L アラニン ザンキ オ ユウスル
  • Synthesis and Properties of Aminimides and Their Crown Derivatives Bearing an L-Alanine Residue
  • L-アラニン残基を有するアミンイミド及びそれらから誘導されるクラウンエーテルの合成と物性

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Abstract

Amphiphilic aminimides (2) possessing two hydroxyl groups and an L-alanine residue were prepared by the reaction of N-alkanoyl-L-alanine methyl esters (1) with N, N-dimethylhydra zine and glycidol. 18-Crown-6 derivatives (3) having an L-alanine residue and a aminimide group were prepared by the reaction between (2) and pentaethylene glycol ditosylate in THF in the presence of NaH (Scheme-1 ).<BR>Some aqueous solution properties of (2) and (3), complexing stability constants (log K'1) for (3) with K+ ion, and liquid membrane transport of N-benzoylamino acid anions mediated by (3) were examined.<BR>All of the surface-active compounds prepared in this investigation were highly soluble in water (cloud point > 100°C). In spite of lower complexing stability constants for (3 a) with K+ ion, the transport efficiency of (3 a) for N-benzoylglycine, -alanine, and-sarcosine were larger than those of the reference compounds without L-alanine residue (5 a), (6), and(7). The result indicates that the hydrogen-bonding interaction between the carrier and substrate can be an important factor to control the transport of the amino acid anions.

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