1. By means of physical methods (IR and NMR spectra, ORD curves, dipole moments) and a theoretical conformational analysis, a study has been made of the conformational states of three topochemical analogs of valinomycin: cyclo-(D-Val-D-HyIv-L-Val-L-Lac)3 (II), cyclo-(D-HyIv-L-Ala-L-HyIv-D-Val)3 (III), and cyclo-(D-HyIv-D-Val-L-HyIv-L-Ala)3 (IV).
2. In compounds (II) and (III) steric interactions prevent the formation of “bracelet” conformations and the formation of complexes with alkali-metal ions.
3. In nonpolar media, compound (IV) assumes a “bracelet” conformation similar to that of valinomycin.
4. In view of steric hindrance, compound (IV) is incapable of adopting the “propeller” conformation that is characteristic for valinomycin, which leads to a reduced surface activity.
5. The conformation of the depsipeptide chain of the K+ complex of compound (IV) is similar to the conformation of the K+ complex of valinomycin. However, in it the cation is more feebly shielded from interaction with the solvent, which explains the higher stability and surface activity of the complex.
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Ivanov, V.T., Laine, I.A., Ovchinnikov, Y.A. et al. Relationship between the structure and properties of cyclodepsipeptides of the valinomycin series I. Topochemical analogs. Chem Nat Compd 9, 235–246 (1973). https://doi.org/10.1007/BF00563352
- Conformational State
- Hydroxyisovaleric Acid