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 ).
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.
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.
