A Homologous Series of Persubstituted Cyclodextrin Amino Acids: The Quest for Tubular Self‐Assembly

The synthesis, conformation and diverse self‐assembling patterns of the homologous series of chemically uniform per(6‐amino‐2‐ O ‐carboxymethyl‐6‐deoxy‐3‐ O ‐methyl)‐substituted α‐, β‐ and γ‐cyclodextrins 6a − 6c are reported. Helical self‐assembly of the lowest homologue 6a gave rise to a three‐dimensional system of separate collinear channels. For the higher homologues 6b − 6c , such a unique architecture is prohibited by unfavorable geometrical factors. A comparison has been made with the corresponding series of native and permethylated cyclodextrins, and the role played by hydrogen bonds in promoting tubular architectures has been assessed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)