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Dextrin cyclodextrin
Release Date:
2023-07-11
Cyclodextrins are the products of starch hydrolysis catalyzed by cyclodextrin glucanotransferase (CGTase); they are cyclic oligosaccharides composed of six or more glucose units linked by α-1,4-glycosidic bonds. The most common and extensively studied types are α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin, which consist of six, seven, and eight glucose units, respectively, and are relatively large and flexible molecules. X-ray diffraction and nuclear magnetic resonance studies have demonstrated that cyclodextrin molecules adopt a conical or truncated-cone-shaped ring structure, featuring numerous rotatable bonds and hydroxyl groups, with an internal cavity whose external appearance resembles a rubber stopper used in tubing. Within the cavity, glycosidic oxygen atoms are arranged such that the lone pairs on these oxygen atoms point toward the center, resulting in a high electron density inside the cavity and imparting partial Lewis-base character. The molecular configuration is that of the C-1 chair conformation of glucose, with the O atom of the glycosidic bond located within the cylindrical interior, thereby conferring hydrophobicity. The 2- and 3-hydroxyl groups of glucose are situated at one end of the cylinder, while the 6-hydroxyl group is at the opposite end; consequently, both ends of the cylinder are hydrophilic. Thus, the inner upper, middle, and lower regions of the cyclodextrin’s cylindrical structure are composed of distinct functional groups.
Cyclodextrins are the products of starch hydrolysis catalyzed by cyclodextrin glucanotransferase (CGTase); they are cyclic oligosaccharides composed of six or more glucose units linked by α-1,4-glycosidic bonds. The most common and extensively studied types are α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin, which consist of six, seven, and eight glucose units, respectively, and are relatively large and flexible molecules. X-ray diffraction and nuclear magnetic resonance studies have demonstrated that cyclodextrin molecules adopt a conical or truncated-cone-shaped ring structure, featuring numerous rotatable bonds and hydroxyl groups, with an internal cavity whose external appearance resembles a rubber stopper used in tubing. Within this cavity, glycosidic oxygen atoms are arranged such that the lone pairs of the oxygen atoms point toward the center, resulting in a high electron density inside the cavity and imparting partial Lewis-base character. The molecular configuration corresponds to the chair conformation at C-1 of the glucose unit, and the O atom involved in the glycosidic linkage is located on the inner surface of the cylindrical cavity, rendering the interior hydrophobic. The –OH groups at the 2- and 3-positions of the glucose unit are situated at one end of the cylinder, while the –OH group at the 6-position is at the opposite end; consequently, both ends of the cylinder are hydrophilic. Thus, the upper, middle, and lower regions of the cyclodextrin’s cylindrical cavity are composed of distinct functional groups.
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