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Relationship between the structure and properties of cyclodepsipeptides of the valinomycin series I. Topochemical analogs

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Summary

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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Additional information

M. M. Shemyakin Institute of the Chemistry of Natural Compounds, Academy of Sciences of the USSR. Institute of the Biochemistry and Physiology of Microorganisms, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 248–263, March–April, 1973.

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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

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Keywords

  • Conformational State
  • Valinomycin
  • Depsipeptides
  • Valino
  • Hydroxyisovaleric Acid