Adamantyl-and tert-butyl-substituted calyx [8]arene esters and tripodal podand containing diphenylphosphoryl terminal groups are capable of transporting monosaccharides, but not disaccharides, across a bulk chloroform membrane. Both stoichiometry of complex formation and transport selectivity, in particular, glucose-fructose selectivity, are sensitive to the structure of a carrier.Key words: transport across a bulk liquid membrane, "host--guest" complexation; substituted calyx [S]arenes, podands; monosaccharides, disaccharides.Needs of biotechnology and pharmacology motivate interest in novel synthetic reagents for binding polyhydroxy compounds, in particular, monosaccharides and their derivatives. Synthetic membrane systems are of special interest. In our opinion, complex formation of the "host--guest" type is quite promising for creating such systems) -5 Certainly, a reagent:host" has to form firm hydrogen bonds with sugars and be lipophilic enough.The great majority of investigations in the field of transport across membranes with synthetic reagents is devoted to ionic transport, while data concerning electroneutral compounds, in particular as hydrophilic as sugars, are poorly reported. For example, transport of sugars with derivatives of boric acid has been studied, but this case does not deal with "host--guest" complexation, a Earlier, we used substituted calyx[8]arenes and podands for binding amines. 7 Those reagents are lipophilic and contain functional groups capable of forming hydrogen bonds with sugars. In the present work, we attempted to use them as carbohydrate carriers. Membrane transport was studied in a U-shaped tube (d = 19 ram). The membrane was a solution of a reagent-"host" in chloroform (V = 20 mL, C = 1 9 10 -3 mol L-l); an aqueous phase: a solution of sugar (V = 10 mL, C = 0.1 tool L -I) was used as a source solution and distilled water (V = 10 mL) was used as a receiving solution. The content of sugar in the receiving solution was controlled photometrically using a reaction with anthrone, s
Results and Discussion
Monosaccharides and disaccharides (D-glucose, D-d-bose, D-galactose, o-fructose, o-xylose, D-arabinose, maltose, saccharose) cannot be transported across a chloroform membrane without a carrier. The transport also was not observed in the presence of simplest lipophilic reagents capable of forming hydrogen bonds: tetradecyl alcohol and dicyclohexyl-18-crown-6 ether. Substituted calyx[8]arenes 1 and 2 transport monosaccharides (and not disaccharides) across a chloroform membrane. The selectivity of the two reagents is different (Table I). Thus, when reagent 2 is used, hexoses (fructose, galactose, and glucose), which are more hydrophilic than pentoses, are transported with a lower velocity. The transport of pentoses, in turn, substantially varies in effectiveness. Among hexoses, glucose is trans-