Folding of a β-cyclodextrin monosubstituted at its secondary face, revealed by NMR studies of local structural variations

The H-1 NMR study of a CD mono-functionalized at its secondary face is presented. It is shown that mono-(3-Tyr-3-deoxy-altro)-beta-CD undergoes a solvent-dependent conformational change. Passing from organic medium to water, a stable self-inclusion complex is formed. Such a folding is accompanied by a local structural modification of the substituted altrose ring, which can be easily detected from the important variation of its H1-H2 coupling constant. (C) 2000 Elsevier Science Ltd. All rights reserved.