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Front. Chem. | doi: 10.3389/fchem.2018.00091

Theoretical and NMR conformational studies of β-proline oligopeptides with alternating chirality of pyrrolidine units

  • 1Faculty of Fundamental Medicine, Moscow State University, Russia
  • 2Department of Chemistry, Moscow State University, Russia
  • 3Institute of Organic Chemistry, Karlsruher Institut für Technologie, Germany
  • 4Institute of Toxicology and Genetics, Karlsruher Institut für Technologie, Germany
  • 5Institute of Physiologically Active Compounds (RAS), Russia

Synthetic β‐peptides are potential functional mimetics of native α-proteins. A recently developed, novel, synthetic approach provides an effective route to the broad group of β‐proline oligomers with alternating patterns of stereogenic centers. Conformation of the pyrrolidine ring, Z/E isomerism of β‐peptide bonds, and hindered rotation of the neighboring monomers determine the spatial structure of this group of β‐proline oligopeptides. Preferences in structural organization and corresponding thermodynamic properties are determined by NMR spectroscopy, restrained molecular dynamics and quantum mechanics. The studied β‐proline oligopeptides exist in dimethyl sulfoxide solution in a limited number of conformers, with compatible energy of formation and different spatial organization. In the β‐proline tetrapeptide with alternating chirality of composing pyrrolidine units, one of three peptide bonds may exist in an E configuration. For the alternating β‐proline pentapeptide, the presence of an E configuration for at least of one β‐peptide bond is mandatory. In this case, three peptide bonds synchronously change their configurations. Larger polypeptides may only exist in the presence of several E configurations of β‐peptide bonds forming a wave-like extended structure.

Keywords: β-Peptides, folding, NMR spectroscopy, Solution structure, restrained molecular dynamics, density functional theory (DFT) calculations

Received: 04 Nov 2017; Accepted: 14 Mar 2018.

Edited by:

Alireza Mashaghi, Kavli Institute of Nanoscience, Delft University of Technology, Netherlands

Reviewed by:

György Tarczay, Eötvös Loránd University, Hungary
Emeric Miclet, Université Pierre et Marie Curie, France
Fernando Porcelli, Università degli Studi della Tuscia, Italy
Vladimir Kubyshkin, Technische Universität Berlin, Germany  

Copyright: © 2018 Mantsyzov, Savelyev, Ivantcova, Bräse, Kudryavtsev and Polshakov. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

* Correspondence: Dr. Vladimir I. Polshakov, Moscow State University, Faculty of Fundamental Medicine, 27/1 Lomonosovsky ave, Moscow, 119991, Russia,