Abstract
The type of bonded phase for HPLC based on the class of oligosaccharides known as cyclodextrins employs inclusion complexing to achieve chiral selectivity. How inclusion complexing accomplishes this is best understood by examining the physical structure of cyclodextrins. Cyclodextrins are toroidally shaped molecules containing from six to twelve glucose units bonded through α-(1,4) linkages (Figure 8. I). The physical shape of the molecule is that of a
Cyclodextrin molecule
Geometry of β-cyclodextrin. From Cyclobond Handbook.
truncated cone, the internal diameter of which is proportional to the number of glucose units. Due to the orientation of the glucose units, there are no hydroxyls on the interior cavity and it is therefore relatively hydrophobic. Each glucose unit contributes five chiral centres to the molecule, and the 2- hydroxyl groups at the entrance of the cavity are orientated in a clockwise direction. This can best be appreciated by studying Figure 8.2 which shows the geometry of β-cyclodextrin.
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References
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© 1989 Chapman & Hall
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Coventry, L. (1989). Cyclodextrin inclusion complexation. In: Lough, W.J. (eds) Chiral Liquid Chromatography. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0861-1_8
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DOI: https://doi.org/10.1007/978-94-009-0861-1_8
Publisher Name: Springer, Dordrecht
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