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Bridged bicyclic peptides as potential drug scaffolds

  • Double cyclization of short linear peptides obtained by solid phase peptide synthesis was used to prepare bridged bicyclic peptides (BBPs) corresponding to the topology of bridged bicyclic alkanes such as norbornane. Diastereomeric norbornapeptides were investigated by 1H-NMR, X-ray crystallography and CD spectroscopy and found to represent rigid globular scaffolds stabilized by intramolecular backbone hydrogen bonds with scaffold geometries determined by the chirality of amino acid residues and sharing structural features of β-turns and α-helices. Proteome profiling by capture compound mass spectrometry (CCMS) led to the discovery of the norbornapeptide 27c binding selectively to calmodulin as an example of a BBP protein binder. This and other BBPs showed high stability towards proteolytic degradation in serum.

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Author:Marco Bartoloni, Xian Jin, Maria José Marcaida, Joao Banha, Ivan Dibonaventura, Swathi Bongoni, Kathrin Bartho, Olivia Gräbner, Michael Sefkow, Tamis Darbre, Jean-Louis Reymond
Subtitle (German):synthesis, structure, protein binding and stability
Series (Serial Number):Postprints der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe (197)
Document Type:Postprint
Year of Completion:2015
Publishing Institution:Universität Potsdam
Release Date:2015/09/25
Source:Chem. Sci., 2015, 6, 5473-5490 - DOI: 10.1039/c5sc01699a
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer Review:Referiert
Publication Way:Open Access
Licence (English):License LogoCreative Commons - Attribution 3.0 unported
Notes extern:Bibliographieeintrag der Originalveröffentlichung/Quelle