MOLECULAR MODELING OF SACCHARIDES .10. STUDIES ON KETOSES .12. THE ELECTROSTATIC AND LIPOPHILIC POTENTIAL PROFILES OF ALPHA-CYCLOFRUCTIN - COMPUTATION, VISUALIZATION AND CONCLUSIONS
S. Immel et Fw. Lichtenthaler, MOLECULAR MODELING OF SACCHARIDES .10. STUDIES ON KETOSES .12. THE ELECTROSTATIC AND LIPOPHILIC POTENTIAL PROFILES OF ALPHA-CYCLOFRUCTIN - COMPUTATION, VISUALIZATION AND CONCLUSIONS, Liebigs Annalen, (1), 1996, pp. 39-44
On the basis of the color-coded visualization of molecular electrostat
ic (MEP) and lipophilicity potential (MLP) profiles, the structural di
fferences and similarities between cyclo-beta(1-->2)-fructohexaoside (
alpha-cyclofructin, 1) and its backbone-derived 18-crown-6 ether and t
he cyclodextrins are outlined. Unlike alpha-cyclodextrin, alpha-cyclof
ructin exhibits no central cavity with which to form inclusion complex
es. Rather, it has a pronounced ''front/back'' differentiation of hydr
ophobic and hydrophilic surface regions. In agreement with experimenta
l observations, the MEP shows not only that the crown ether-type prope
rties of alpha-cyclofructin are well-suited for the complexation of me
tal cations, but also that there is a pronounced regioselectivity for
their incorporation.