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  Stereochemistry Rules: A Single Stereocenter Changes the Conformation of a Cyclic Tetrapeptide

Li, F., Bravo-Rodriguez, K., Fernandez-Oliva, M., Ramirez-Anguita, J. M., Merz, K., Winter, M., et al. (2013). Stereochemistry Rules: A Single Stereocenter Changes the Conformation of a Cyclic Tetrapeptide. The Journal of Physical Chemistry B, 117(37), 10785-10791. doi:10.1021/jp406497r.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0014-A2C3-0 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0019-7C45-2
Genre: Journal Article

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 Creators:
Li, Fee1, Author
Bravo-Rodriguez, Kenny2, Author           
Fernandez-Oliva, Miguel1, Author
Ramirez-Anguita, Juan M.1, Author
Merz, Klaus3, Author
Winter, Manuela4, Author
Lehmann, Christian W.5, Author           
Sander, Wolfram1, Author
Sanchez-Garcia, Elsa2, Author           
Affiliations:
1Lehrstuhl für Organische Chemie II, Ruhr-Universität Bochum, D-44801 Bochum, Germany, ou_persistent22              
2Research Group Sánchez-García, Max-Planck-Institut für Kohlenforschung, Max Planck Society, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, DE, ou_1950289              
3Lehrstuhl für Anorganische Chemie I, Ruhr-Universität Bochum, D-44801 Bochum, Germany, ou_persistent22              
4Lehrstuhl für Anorganische Chemie II, Ruhr-Universität Bochum, D-44801 Bochum, Germany, ou_persistent22              
5Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, DE, ou_1445625              

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 Abstract: Two novel cyclo(Boc-Cys-Pro-Leu-Cys-OMe) peptides 1 and 2 containing the enantiomeric amino acids D-Leu and L-Leu, respectively, were synthesized to investigate the effect of chiral centers on peptide conformations. By combining a variety of experimental techniques (X-ray crystallography, 2D NMR spectroscopy, temperaturedependent 1H NMR and IR spectroscopy, and UV-CD spectroscopy) with replica exchange molecular dynamics (REMD) techniques and quantum mechanics/molecular dynamics (QM/MM) calculations, we establish that the stereochemistry of just one residue can noticeably influence the properties of the whole peptide and rationalize the origins of this effect, with potential implications for the rational design of peptides of chemical and biological relevance.

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Language(s): eng - English
 Dates: 2013-08-132013-07-012013-09-062013-09-19
 Publication Status: Issued
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jp406497r
 Degree: -

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Title: The Journal of Physical Chemistry B
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: 7 Volume / Issue: 117 (37) Sequence Number: - Start / End Page: 10785 - 10791 Identifier: ISSN: 1520-6106
CoNE: https://pure.mpg.de/cone/journals/resource/1000000000293370_1