Synthesis, Structure, and Conformational Features of α-Cycloaltrin: A Cycloeligosaccharide with Alternating 4C1/1C4 Pyranoid Chairs

Authors

  • Prof. Yasuyoshi Nogami,

    1. Daiichi College of Pharmaceutical Sciences, Fukuoka 815 (Japan), Fax: Int. code +(925)53-5698
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  • Kyoko Nasu,

    1. Daiichi College of Pharmaceutical Sciences, Fukuoka 815 (Japan), Fax: Int. code +(925)53-5698
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  • Prof. Toshitaka Koga,

    1. Daiichi College of Pharmaceutical Sciences, Fukuoka 815 (Japan), Fax: Int. code +(925)53-5698
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  • Kazuko Ohta,

    1. Faculty of Pharmaceutical Sciences Nagasaki University Nagasaki 852 (Japan) Fax: Int. code + (958)46-5736
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  • Prof. Kahee Fujita,

    Corresponding author
    1. Faculty of Pharmaceutical Sciences Nagasaki University Nagasaki 852 (Japan) Fax: Int. code + (958)46-5736
    • Faculty of Pharmaceutical Nagasaki University Nagasaki 852 (Japan) Fax: Inrt. code + (958)46-5736
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  • Dr. Stefan Immel,

    1. Institut für Organische Chemie der Technischen Hochschule D-64287 Darmstadt (Germany), Fax: Int. code +(6151)16-6674
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  • Prof. Dr. Hans J. Lindner,

    1. Institut für Organische Chemie der Technischen Hochschule D-64287 Darmstadt (Germany), Fax: Int. code +(6151)16-6674
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  • Dipl.-Ing. Guido E. Schmitt,

    1. Institut für Organische Chemie der Technischen Hochschule D-64287 Darmstadt (Germany), Fax: Int. code +(6151)16-6674
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  • Prof. Dr. Frieder W. Lichtenthaler

    Corresponding author
    1. Institut für Organische Chemie der Technischen Hochschule D-64287 Darmstadt (Germany), Fax: Int. code +(6151)16-6674
    • Institut für Organische Chemie der Technischen Hochschule D-64287 Darmstadt (Germany), Fax: Int. code +(6151)16-6674
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  • Molecular Modeling of Saccharides, PArt 15. This work was supported by the Fonds der Chemischen Industrie and the Nihon Shokuhin Kako (Japan Maize Products Co.) Part 14: Ref.[2]

Abstract

original image

A cavity closed on one side is evident in the solid-state structure of α-cycloaltrin (see picture on the right). This novel non-glucose cyclooligosaccharide is constructed of alternating 1C4 and 4C1 chair conformations of the altropyranoid rings. In aqueous solution an equilibrium between the 1C4 and 0S2 (skew) forms is established. α-Cycloaltrin is prepared from α-Cyclodextrin in a straightforward four-step protocol in which the 2,3-anhydro-α-cyclomannin is the key intermediate.

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