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A study of the conformational states of cyclopeptide systems IV. NMR spectra of cyclohexapeptides constructed of alanine and glycine residues: Chemical shifts and intramolecular hydrogen bonds

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Chemistry of Natural Compounds Aims and scope

Summary

1. The NMR spectra of cyclohexapeptides constructed of L(D)-alanine and glycine residues have been studied in (CD3)2SO, CF3COOH, and H2O solutions.

2. In all the compounds studied, the amide bonds assume the trans configuration.

3. In polar solvents, the cyclohexapeptides assume the "pleated-sheet" conformation characterized by two trans-annular hydrogen bonds of the 4→1 type.

4. The dominating structure of the cyclohexapeptides is in equilibrium with two analogous structures accompanied by the migration of the system of H bonds with respect to the ring.

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Authors and Affiliations

  1. Chemical Faculty of the Polytechnic Institute, Gdansk, Poland

    S. L. Portnova, T. A. Balashova, V. F. Bystrov, V. V. Shilin, Ya. Bernat, V. T. Ivanov & Yu. A. Ovchinnikov

Authors
  1. S. L. Portnova
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  2. T. A. Balashova
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  3. V. F. Bystrov
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  4. V. V. Shilin
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  5. Ya. Bernat
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  6. V. T. Ivanov
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  7. Yu. A. Ovchinnikov
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Additional information

For the preceding communication, see [1].

M. M. Shemyakin Institute of the Chemistry of Natural Compounds of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 323–338, May–June, 1971.

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Portnova, S.L., Balashova, T.A., Bystrov, V.F. et al. A study of the conformational states of cyclopeptide systems IV. NMR spectra of cyclohexapeptides constructed of alanine and glycine residues: Chemical shifts and intramolecular hydrogen bonds. Chem Nat Compd 7, 307–318 (1971). https://doi.org/10.1007/BF00569005

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  • DOI: https://doi.org/10.1007/BF00569005

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