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  Solvent‐Enhanced Conformational Flexibility of Cyclic Tetrapeptides

Berger, N., Wollny, L. J. B., Sokkar, P., Mittal, S., Mieres-Perez, J., Stoll, R., et al. (2019). Solvent‐Enhanced Conformational Flexibility of Cyclic Tetrapeptides. ChemPhysChem, 20(13), 1664-1670. doi:10.1002/cphc.201900345.

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 Creators:
Berger, Nadja1, Author
Wollny, Laura J. B.2, Author              
Sokkar, Pandian2, 3, Author              
Mittal, Sumit2, 3, Author              
Mieres-Perez, Joel3, Author
Stoll, Raphael4, Author
Sander, Wolfram1, Author
Sanchez-Garcia, Elsa2, 3, Author              
Affiliations:
1Organische Chemie II, Ruhr-University of Bochum, Universitätsstr. 150, 44780 Bochum, Germany, ou_persistent22              
2Research Group Sánchez-García, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1950289              
3Computational Biochemistry, Center of Medical Biotechnology, University of Duisburg-Essen, Universitätsstr. 2, 45141 Essen, ou_persistent22              
4Biomolecular NMR Spectroscopy, Ruhr-University of Bochum, Universitätsstr. 150, 44780 Bochum, Germany, ou_persistent22              

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Free keywords: cyclic peptides; NMR spectroscopy; IR spectroscopy; Replica Exchange Molecular Dynamics; Quantum Mechanics/Molecular Mechanics
 Abstract: Solvent and temperature can affect the structural properties of cyclic peptides by controlling their flexibility. Here, we investigate two cyclic peptides, featuring beta turns. Using temperature‐dependent NMR and FT‐IR, we observed a pronounced temperature effect on the conformation of the cyclic peptide D‐1 in CHCl3 but a much smaller effect in CH3CN. Almost no effect was observed for its diastereomer L‐1 within a similar temperature range and using the same solvents. With the aid of Replica Exchange Molecular Dynamics simulations and Quantum Mechanics/Molecular Mechanics calculations, we were able to explain this behavior based on the increased flexibility of D‐1 (in CHCl3) in terms of intramolecular hydrogen bonding. The largest temperature dependence is observed for D‐1 in CHCl3, while the temperature effect is less pronounced for L‐1 in CHCl3 and for both peptides in CH3CN. This work provides new insights into the role of the environment and temperature on the conformations of cyclic peptides.

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Language(s): eng - English
 Dates: 2019-04-082019-05-022019-07-02
 Publication Status: Published online
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/cphc.201900345
 Degree: -

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Title: ChemPhysChem
Source Genre: Journal
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Publ. Info: Weinheim, Germany : Wiley-VCH
Pages: - Volume / Issue: 20 (13) Sequence Number: - Start / End Page: 1664 - 1670 Identifier: ISSN: 1439-4235
CoNE: https://pure.mpg.de/cone/journals/resource/954925409790