Preparation and characterization of 6A-polyamine-mono-substituted β-cyclodextrins

Abstract

General syntheses for eleven β-cyclodextrins (cyclomaltoheptaoses) mono-substituted at the C6 position by a polyamine are described. The basis of the synthesis is the reaction of 6^A-O-(4-methylphenylsulfonyl)-β-cyclodextrin in the presence of KI in 1-methylpyrrolidin-2-one solution. This produces a clean product and obviates the substantial purification procedures which other preparative methods often entail. Systematic studies of the variations of the pK_as of the protonated amine groups and the ¹³C NMR spectra of the modified β-cyclodextrins with pH are reported.