Conformational analysis of atropine.
The conformation of atropine was studied by nmr and dipole moment measurements. It was shown that there is a cis conformation between the C = O bond in the ester group and the tropanyl group. The nmr measurements indicated that the Ph--CH(CH2OH)--CO-- grouping assumes conformations I and II in equilibrium, while the conformational isomer III can be excluded. Consequently, the distance between the nitrogen atom and the carbonyl group is 4.5--5.0 A, and this determines the binding to the cholinergic receptor. This distance is substantially less than the 7 A presumed by other authors earlier.
D001285:Atropine; D001665:Binding Sites; D004952:Esters; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011048:Polarography; D013696:Temperature; D014326:Tropanes
D004952:Esters; D014326:Tropanes; D001285:Atropine