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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.