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Article

Macrocyclic Tetramers—Structural Investigation of Peptide-Peptoid Hybrids

by
Claudine Nicole Herlan
1,
Anna Sonnefeld
2,
Thomas Gloge
2,
Julian Brückel
1,
Luisa Chiara Schlee
1,
Claudia Muhle-Goll
2,
Martin Nieger
3 and
Stefan Bräse
1,4,*
1
Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
2
Institute for Biological Interfaces 4, Karlsruhe Institute of Technology, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
3
Department of Chemistry, University of Helsinki, P.O. Box 55 (A.I. Virtasen aukio 1), FIN-00014 Helsinki, Finland
4
Institute of Biological and Chemical Systems—Functional Molecular Systems, Karlsruhe Institute of Technology, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(15), 4548; https://doi.org/10.3390/molecules26154548
Submission received: 7 July 2021 / Revised: 23 July 2021 / Accepted: 24 July 2021 / Published: 28 July 2021
(This article belongs to the Section Chemical Biology)
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Abstract

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.
Keywords: macrocycles; multiconformational equilibrium; peptidomimetics; peptoids; spatial structure; tetramers macrocycles; multiconformational equilibrium; peptidomimetics; peptoids; spatial structure; tetramers

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MDPI and ACS Style

Herlan, C.N.; Sonnefeld, A.; Gloge, T.; Brückel, J.; Schlee, L.C.; Muhle-Goll, C.; Nieger, M.; Bräse, S. Macrocyclic Tetramers—Structural Investigation of Peptide-Peptoid Hybrids. Molecules 2021, 26, 4548. https://doi.org/10.3390/molecules26154548

AMA Style

Herlan CN, Sonnefeld A, Gloge T, Brückel J, Schlee LC, Muhle-Goll C, Nieger M, Bräse S. Macrocyclic Tetramers—Structural Investigation of Peptide-Peptoid Hybrids. Molecules. 2021; 26(15):4548. https://doi.org/10.3390/molecules26154548

Chicago/Turabian Style

Herlan, Claudine Nicole, Anna Sonnefeld, Thomas Gloge, Julian Brückel, Luisa Chiara Schlee, Claudia Muhle-Goll, Martin Nieger, and Stefan Bräse. 2021. "Macrocyclic Tetramers—Structural Investigation of Peptide-Peptoid Hybrids" Molecules 26, no. 15: 4548. https://doi.org/10.3390/molecules26154548

APA Style

Herlan, C. N., Sonnefeld, A., Gloge, T., Brückel, J., Schlee, L. C., Muhle-Goll, C., Nieger, M., & Bräse, S. (2021). Macrocyclic Tetramers—Structural Investigation of Peptide-Peptoid Hybrids. Molecules, 26(15), 4548. https://doi.org/10.3390/molecules26154548

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