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Structure and Lipophilicity Profile of 2, 3‐Anhydro‐ α ‐cyclomannin and Its Ethanol Inclusion Complex
Author(s) -
Immel Stefan,
Fujita Kahee,
Lindner Hans J.,
Nogami Yasuyoshi,
Lichtenthaler Frieder W.
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20000703)6:13<2327::aid-chem2327>3.0.co;2-v
Subject(s) - lipophilicity , chemistry , ethanol , stereochemistry , crystallography , epoxide , organic chemistry , catalysis
Readily available from α ‐cyclodextrin in three steps, 2,3‐anhydro‐ α ‐cyclomannin composed of six α ‐(1→4)‐linked 2,3‐anhydro‐ D ‐mannopyranose residues, crystallizes well when precipitated from aqueous ethanol. An X‐ray structure reveals the macrocycle to contain ethanol in its cavity, thus representing the first inclusion complex of a non‐glucose cyclooligosaccharide. The wider rim of the torus‐shaped macrocycle holds the six epoxide rings whose oxygens point away from the cavity, thereby sculpturing the unique over‐all shape of a six‐pointed star.