Chemistry of Natural Compounds

, Volume 7, Issue 3, pp 307–318 | Cite as

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

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

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.

Keywords

Nuclear Magnetic Resonance Spectrum Glycine Residue CF3COOH Deuterium Exchange Alanine Residue 

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Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1973

Authors and Affiliations

  • S. L. Portnova
    • 1
  • T. A. Balashova
    • 1
  • V. F. Bystrov
    • 1
  • V. V. Shilin
    • 1
  • Ya. Bernat
    • 1
  • V. T. Ivanov
    • 1
  • Yu. A. Ovchinnikov
    • 1
  1. 1.Chemical Faculty of the Polytechnic InstituteGdanskPoland

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