Structure and lipophilicity profile of 2,3-anhydro-alpha-cyclomannin and its ethanol inclusion complex.
Readily available from alpha-cyclodextrin in three steps, 2,3-anhydro-alpha-cyclomannin composed of six alpha-(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.
Institut für Organische Chemie, Technische Universität Darmstadt, Germany.
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Immel
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Fujita
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HJ
Lindner
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Y
Nogami
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Lichtenthaler
D002240:Carbohydrate Sequence; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004852:Epoxy Compounds / Q000737:chemistry*; D000431:Ethanol / Q000737:chemistry*; D006860:Hydrogen Bonding; D008055:Lipids / Q000737:chemistry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*; D014961:X-Ray Diffraction
C413143:2,3-anhydro-cyclomannin; D004852:Epoxy Compounds; D008055:Lipids; D009844:Oligosaccharides; D011714:Pyrans; D000431:Ethanol