Molecular Modelling of Saccharides, 10 Studies on Ketoses, 12 The Electrostatic and Lipophilic Potential Profiles of α‐Cyclofructin: Computation, Visualization and Conclusions

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, 1 ) 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.