Characterization and structural determination of 3A-amino-3A-deoxy-(2AS, 3AS)-cyclodextrins by NMR spectroscopy

Abstract

The proton and carbon nuclear magnetic resonance (NMR) resonances have been assigned for 3A-amino-3A-deoxy-(2AS,3AS)-α-, Β- and γ-cyclodextrins (CyDs) (3α, 3Β and 3γ). In these CyDs, a glucose residue has been replaced by an altro-pyranose unit with an axial hydroxyl group. Assignments were made with one-dimensional NMR and COSY, TOCSY, ROESY and CHSHF (heteronuclear shift correlation) spectra. Titration by NMR shift changes gave amino-group pK a values of 7.73 and 8.84 for 3Β and 6A-amino-6A-deoxy-Β-CyD (6Β), respectively. © 2012 The Society of Polymer Science, Japan (SPSJ) All rights reserved.