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Macrocyclic tetramers—structural investigation of peptide-peptoid hybrids

Herlan, Claudine Nicole 1; Sonnefeld, Anna 2; Gloge, Thomas 2; Brückel, Julian 1; Schlee, Luisa Chiara 1; Muhle-Goll, Claudia ORCID iD icon 2; Nieger, Martin; Bräse, Stefan 1
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)
2 Institut für Biologische Grenzflächen (IBG), Karlsruher Institut für Technologie (KIT)


Outstanding affinity and specificity are the main characteristics of peptides, rendering them interesting compounds for basic and medicinal research. However, their biological applicability is limited due to fast proteolytic degradation. The use of mimetic peptoids overcomes this disadvantage, though they lack stereochemical information at the α-carbon. Hybrids composed of amino acids and peptoid monomers combine the unique properties of both parent classes. Rigidification of the backbone increases the affinity towards various targets. However, only little is known about the spatial structure of such constrained hybrids. The determination of the three-dimensional structure is a key step for the identification of new targets as well as the rational design of bioactive compounds. Herein, we report the synthesis and the structural elucidation of novel tetrameric macrocycles. Measurements were taken in solid and solution states with the help of X-ray scattering and NMR spectroscopy. The investigations made will help to find diverse applications for this new, promising compound class.

Verlagsausgabe §
DOI: 10.5445/IR/1000136984
Veröffentlicht am 26.11.2021
DOI: 10.3390/molecules26154548
Zitationen: 1
Web of Science
Zitationen: 1
Zitationen: 1
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische Grenzflächen (IBG)
Institut für Biologische und Chemische Systeme (IBCS)
Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 08.07.2021
Sprache Englisch
Identifikator ISSN: 1420-3049
KITopen-ID: 1000136984
HGF-Programm 43.33.11 (POF IV, LK 01) Adaptive and Bioinstructive Materials Systems
Erschienen in Molecules
Verlag MDPI
Band 26
Heft 15
Seiten Art.Nr. 4548
Bemerkung zur Veröffentlichung Gefördert durch den KIT-Publikationsfonds
Schlagwörter macrocycles; multiconformational equilibrium; peptidomimetics; peptoids; spatial structure; tetramers
Nachgewiesen in Dimensions
Web of Science
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