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Molecular Modeling of Saccharides, Part X.

The Electrostatic and Lipophilic Potential Profiles of α-Cyclofructin: Computation, Visualization and Inferences

Stefan Immel and Frieder W. Lichtenthaler

Liebigs Ann. 1996, 39-44.

On the basis of the color-coded visualization of molecular electrostatic (MEP) and lipophilicity potential (MLP) profiles, the structural differences and similarities between cyclo-β(1→2)-fructohexaoside (α-cyclofructin) and its backbone-derived 18-crown-6 ether and the cyclodextrins are outlined. Unlike α-cyclodextrin, α-cyclofructin exhibits no central cavity with which to form inclusion complexes. Rather, it has a pronounced front-back differentiation of hydrophobic and hydrophilic surface regions. In agreement with experimental observations, the MEP shows not only that the crown ether-type properties of α-cyclofructin are well-suited for the complexation of metal cations, but also that there is a pronounced regioselectivity for their incorporation.

Additional Graphics: Cyclofructins

© Copyright PD Dr. S. Immel