Retention behavior of positional isomers of disubstituted cyclomalto-oligosaccharide (cyclodextrin) derivatives on an ODS column.

The correlation between hydrophobic effects and structures of three and four positional isomers of 6(1),6n-di-O-triphenylmethyl (trityl)- or 6(1),6n-di-O-tert.- butyldimethylsilyl (tert.-BuMe2Si)-cyclomaltohexaoses (cG6s, alpha-cyclodextrin) (n = 2-4), -cyclomaltoheptaoses (cG7s, beta-cyclodextrin) (n = 2-4), and -cyclomaltooctaoses (cG8s, gamma-cyclodextrin) (n = 2-5) on an ODS column are discussed. Cyclodextrins with two hydrophobic-substituted groups bonded to hydroxyl groups tended to show low retention of positional isomers in which the binding positions of the two substituted groups on the cyclodextrin ring were far apart from each other.