No abstract

The ability of γ-amino-propylboronic acids to transport phenyl ß-D-glucopyranoside and phenyl ß-D-galactopyranoside through a liquid organic membrane in the presence of trioctylmethylammonuim chloride was determined. Under the conditions examined, glycoside transport was facilitated by the reversible formation of covalent tetrahedral, anionic glycosideboronate complexes, which partitioned into the organic membrane as lipophilic ion pairs. The apparent order of glycoside selectivity for the tetrahedral boronate transport was to be cis α,γ-diol> α,β-diol. The results indicate that the N->B intramolecular dative bond and the Hydrophile-Lipophile-Balance (HLB) of the formed complex influence the glycoside transport rate.