Open Access
Frontiers in Chemistry, volume 6
Theoretical and NMR conformational studies of β-proline oligopeptides with alternating chirality of pyrrolidine units
Publication type: Journal Article
Publication date: 2018-03-28
Journal:
Frontiers in Chemistry
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor: 5.5
ISSN: 22962646
PubMed ID:
29644215
General Chemistry
Abstract
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 their 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.
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Mantsyzov A. B. et al. Theoretical and NMR conformational studies of β-proline oligopeptides with alternating chirality of pyrrolidine units // Frontiers in Chemistry. 2018. Vol. 6.
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Mantsyzov A. B., Savelyev O. Y., Ivantcova P. M., Bräse S., Kudryavtsev K. V., Polshakov V. I. Theoretical and NMR conformational studies of β-proline oligopeptides with alternating chirality of pyrrolidine units // Frontiers in Chemistry. 2018. Vol. 6.
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TY - JOUR
DO - 10.3389/fchem.2018.00091
UR - https://doi.org/10.3389%2Ffchem.2018.00091
TI - Theoretical and NMR conformational studies of β-proline oligopeptides with alternating chirality of pyrrolidine units
T2 - Frontiers in Chemistry
AU - Mantsyzov, Alexey B
AU - Savelyev, Oleg Y
AU - Ivantcova, Polina M.
AU - Bräse, Stefan
AU - Kudryavtsev, Konstantin V.
AU - Polshakov, Vladimir I
PY - 2018
DA - 2018/03/28 00:00:00
PB - Frontiers Media S.A.
VL - 6
PMID - 29644215
SN - 2296-2646
ER -
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@article{2018_Mantsyzov,
author = {Alexey B Mantsyzov and Oleg Y Savelyev and Polina M. Ivantcova and Stefan Bräse and Konstantin V. Kudryavtsev and Vladimir I Polshakov},
title = {Theoretical and NMR conformational studies of β-proline oligopeptides with alternating chirality of pyrrolidine units},
journal = {Frontiers in Chemistry},
year = {2018},
volume = {6},
publisher = {Frontiers Media S.A.},
month = {mar},
url = {https://doi.org/10.3389%2Ffchem.2018.00091},
doi = {10.3389/fchem.2018.00091}
}
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