TUD Organische Chemie

Immel

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Abstract 16

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Molecular Modeling of Saccharides, Part XIV.

The Lipophilicity Patterns of Cyclodextrins and of Non-Glucose Cyclooligosaccharides

Frieder W. Lichtenthaler and Stefan Immel

Inclusion Phenom. Mol. Recognit. Chem. 1996, 25, 3-16.
Proceedings of the 8^th Internat. Symp. on Cyclodextrins (Eds.: J. Szejtli, L. Szente), Kluwer Acad. Publ., Dordrecht, NL, 1996, pp. 3-16.

Computer-aided generation of the 3D-geometries and the contact surfaces for the cyclodextrins and cyclooligosaccharides composed of mannose, altrose, galactose, and fructose provides a lucid picture on their molecular architecture, most notably their cavity dimensions. The MOLCAD program mediated computation of the molecular lipophilicity patterns (MLPs), projected in color-coded form onto the respective contact surfaces allow for the first time a detailed localization of hydrophobic and hydrophilic domains, which determine to a substantial degree the capabilities of these cyclooligosaccharides for inclusion complex formation.

Additional Graphics: Cyclodextrins / Cyclodextrin Isomers