Synthesis, Structure, and Conformational Features of α‐Cycloaltrin: A Cycloeligosaccharide with Alternating  4  C  1 / 1  C  4  Pyranoid Chairs | Zendy

Nogami Yasuyoshi | Zendy; Nasu Kyoko | Zendy; Koga Toshitaka | Zendy; Ohta Kazuko | Zendy; Fujita Kahee | Zendy; Immel Stefan | Zendy; Lindner Hans J. | Zendy; Schmitt Guido E. | Zendy; Lichtenthaler Frieder W. | Zendy

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Synthesis, Structure, and Conformational Features of α‐Cycloaltrin: A Cycloeligosaccharide with Alternating 4 C 1 / 1 C 4 Pyranoid Chairs

Author(s) -

Nogami Yasuyoshi,

Nasu Kyoko,

Koga Toshitaka,

Ohta Kazuko,

Fujita Kahee,

Immel Stefan,

Lindner Hans J.,

Schmitt Guido E.,

Lichtenthaler Frieder W.

Publication year - 1997

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.199718991

Subject(s) - crystallography , chemistry , solid state , stereochemistry , crystal structure , aqueous solution , physics

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 1 C 4 and 4 C 1 chair conformations of the altropyranoid rings. In aqueous solution an equilibrium between the 1 C 4 and 0 S 2 (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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