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A Homologous Series of Persubstituted Cyclodextrin Amino Acids: The Quest for Tubular Self‐Assembly
Author(s) -
Kraus Tomáš,
Buděšínský Miloš,
Císařová Ivana,
Závada Jiří
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400272
Subject(s) - chemistry , homologous series , self assembly , hydrogen bond , cyclodextrin , stereochemistry , amino acid , supramolecular chemistry , series (stratigraphy) , homologous chromosome , crystallography , molecule , organic chemistry , biochemistry , biology , paleontology , gene
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)