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Polypseudopeptides with Variable Stereochemistry: Synthesis via Click-Chemistry, Postfunctionalization, and Conformational Behavior in Solution

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Department of Chemistry, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489 Berlin, Germany
*Corresponding author. E-mail: [email protected]
Cite this: Macromolecules 2010, 43, 1, 242–248
Publication Date (Web):October 30, 2009
https://doi.org/10.1021/ma902018w
Copyright © 2009 American Chemical Society

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    Abstract

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    Polypseudopeptides with well-defined stereochemistries have been synthesized from readily available amino-acid-based building blocks by connecting (l,l)- or (l,d)-dipeptide AB-monomers carrying azide and alkyne termini via triazole amide-isosteres efficiently formed in the course of the “click” reaction. Deprotection of the thus-prepared lysine-based polypseudopeptides of both all-(l)- and (d)-alt-(l)-stereochemistries afforded water-soluble polymers with ionizable amino side chains, which could be fully labeled with pyrene chromophores via quantitative amide bond formation. The conformational behavior of the deprotected as well as the pyrene-labeled polymers was investigated using UV/vis, CD, and fluorescence spectroscopies. On one hand, the free polyamines display pH-dependent conformations in water. On the other hand, the pyrene-labeled polypseudopeptides change their conformation in response to varying organic solvent composition. Whereas the strictly alternating polypseudopeptides structurally resemble channel-forming peptides, such as the Gramicidin family, the incorporation of (d)-configured amino acids as well as triazole amide-isosteres should lead to interesting new materials for bioapplications.

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    Details of monomer synthesis and polymerization reactions as well as compound characterization data including UV/vis, CD, and NMR spectra as well as chromatography. This material is available free of charge via the Internet at http://pubs.acs.org.

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    2. Zhihai Ke, Hak-Fun Chow, Man-Chor Chan, Zhifeng Liu, and Kong-Hung Sze . Head-to-Tail Dimerization and Organogelating Properties of Click Peptidomimetics. Organic Letters 2012, 14 (1) , 394-397. https://doi.org/10.1021/ol2031685
    3. Jinshan Guo, Ying Wei, Dongfang Zhou, Pingqiang Cai, Xiabin Jing, Xue-Si Chen, and Yubin Huang . Chemosynthesis of Poly(ε-lysine)-Analogous Polymers by Microwave-Assisted Click Polymerization. Biomacromolecules 2011, 12 (3) , 737-746. https://doi.org/10.1021/bm1013662
    4. Anjun Qin, Jacky W. Y. Lam, and Ben Zhong Tang . Click Polymerization: Progresses, Challenges, and Opportunities. Macromolecules 2010, 43 (21) , 8693-8702. https://doi.org/10.1021/ma101064u
    5. Joon-il Cho, Masahiro Tanaka, Sota Sato, Kazushi Kinbara, and Takuzo Aida. Oligo(4-aminopiperidine-4-carboxylic acid): An Unusual Basic Oligopeptide with an Acid-Induced Helical Conformation. Journal of the American Chemical Society 2010, 132 (38) , 13176-13178. https://doi.org/10.1021/ja106118w
    6. Sebastian Hartwig, Jutta Schwarz and Stefan Hecht. From Peptides to Their Alternating Ester-Urea Analogues: Synthesis and Influence of Hydrogen Bonding Motif and Stereochemistry on Aggregation. The Journal of Organic Chemistry 2010, 75 (3) , 772-782. https://doi.org/10.1021/jo902249w
    7. Sheela Kumari, Sain Singh, Kaushik Ghosh. Azide‐Alkyne Cycloaddition Reaction Catalyzed by Cu(II) Complexes: Studies on the effect of Different Ligand Systems. ChemistrySelect 2023, 8 (32) https://doi.org/10.1002/slct.202301003
    8. Mesut Görür. Click Chemistry Approaches for the Synthesis and Functionalization of Macromolecules. Journal of Composites and Biodegradable Polymers 2021, 9 , 46-54. https://doi.org/10.12974/2311-8717.2021.09.05
    9. Randhir Rai, Dillip Kumar Chand. Multicomponent click reactions catalysed by copper(I) oxide nanoparticles (Cu2ONPs) derived using Oryza sativa. Journal of Chemical Sciences 2020, 132 (1) https://doi.org/10.1007/s12039-020-01774-5
    10. Lisa-Maria Rečnik, Wolfgang Kandioller, Thomas L. Mindt. 1,4-Disubstituted 1,2,3-Triazoles as Amide Bond Surrogates for the Stabilisation of Linear Peptides with Biological Activity. Molecules 2020, 25 (16) , 3576. https://doi.org/10.3390/molecules25163576
    11. David C. Schröder, Oliver Kracker, Tanja Fröhr, Jerzy Góra, Michał Jewginski, Anke Nieß, Iris Antes, Rafał Latajka, Antoine Marion, Norbert Sewald. 1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties. Frontiers in Chemistry 2019, 7 https://doi.org/10.3389/fchem.2019.00155
    12. Frederike M. Müskens, Richard J. Ward, Dominik Herkt, Helmus van de Langemheen, Andrew B. Tobin, Rob M. J. Liskamp, Graeme Milligan. Design, Synthesis, and Evaluation of a Diazirine Photoaffinity Probe for Ligand-Based Receptor Capture Targeting G Protein–Coupled Receptors. Molecular Pharmacology 2019, 95 (2) , 196-209. https://doi.org/10.1124/mol.118.114249
    13. Sima Abbaspour, Ali Keivanloo, Mohammad Bakherad, Saghi Sepehri. Salophen Copper(II) Complex‐Assisted Click Reactions for Fast Synthesis of 1,2,3‐Triazoles Based on Naphthalene‐1,4‐dione Scaffold, Antibacterial Evaluation, and Molecular Docking Studies. Chemistry & Biodiversity 2019, 16 (1) https://doi.org/10.1002/cbdv.201800410
    14. Die Huang, AnJun Qin, Ben Zhong Tang. Overview of Click Polymerization. 2018, 1-35. https://doi.org/10.1039/9781788010108-00001
    15. Arthi Ravi, Kana M. Sureshan. Tunable Mechanical Response from a Crystal Undergoing Topochemical Dimerization: Instant Explosion at a Faster Rate and Chemical Storage of a Harvestable Explosion at a Slower Rate. Angewandte Chemie 2018, 130 (30) , 9506-9510. https://doi.org/10.1002/ange.201804589
    16. Arthi Ravi, Kana M. Sureshan. Tunable Mechanical Response from a Crystal Undergoing Topochemical Dimerization: Instant Explosion at a Faster Rate and Chemical Storage of a Harvestable Explosion at a Slower Rate. Angewandte Chemie International Edition 2018, 57 (30) , 9362-9366. https://doi.org/10.1002/anie.201804589
    17. Daniela M. Fidalgo, Adriana A. Kolender, Oscar Varela. Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers. Materials Today Communications 2015, 2 , e70-e83. https://doi.org/10.1016/j.mtcomm.2014.12.001
    18. Jarrad M. Altimari, Birunthi Niranjan, Gail P. Risbridger, Stephanie S. Schweiker, Anna E. Lohning, Luke C. Henderson. Preliminary investigations into triazole derived androgen receptor antagonists. Bioorganic & Medicinal Chemistry 2014, 22 (9) , 2692-2706. https://doi.org/10.1016/j.bmc.2014.03.018
    19. Inmaculada Molina-Pinilla, Manuel Bueno-Martínez, Khalid Hakkou, Juan A. Galbis. Linear poly(amide triazole)s derived from d -glucose. Journal of Polymer Science Part A: Polymer Chemistry 2014, 52 (5) , 629-638. https://doi.org/10.1002/pola.27038
    20. N. Jung, S. Bräse. Click Reactions: Azide‐Alkyne Cycloaddition. 2013, 1-43. https://doi.org/10.1002/0471238961.clicjung.a01
    21. Hu Jian, He Jin-lin, Zhang Ming-zu, Ni Pei-hong. APPLICATIONS OF “CLICK” CHEMISTRY IN SYNTHESIS OF TOPOLOGICAL POLYMERS. Acta Polymerica Sinica 2013, 013 (3) , 300-319. https://doi.org/10.3724/SP.J.1105.2013.12336
    22. Shadpour Mallakpour, Mohammad Dinari. Progress in Synthetic Polymers Based on Natural Amino Acids. Journal of Macromolecular Science, Part A 2011, 48 (8) , 644-679. https://doi.org/10.1080/15226514.2011.586289
    23. Christopher Barner‐Kowollik, Filip E. Du Prez, Pieter Espeel, Craig J. Hawker, Tanja Junkers, Helmut Schlaad, Wim Van Camp. Klickreaktionen von Polymeren oder einfach nur effizientes Verknüpfen: Wo liegt der Unterschied?. Angewandte Chemie 2011, 123 (1) , 61-64. https://doi.org/10.1002/ange.201003707
    24. Christopher Barner‐Kowollik, Filip E. Du Prez, Pieter Espeel, Craig J. Hawker, Tanja Junkers, Helmut Schlaad, Wim Van Camp. “Clicking” Polymers or Just Efficient Linking: What Is the Difference?. Angewandte Chemie International Edition 2011, 50 (1) , 60-62. https://doi.org/10.1002/anie.201003707
    25. Silvia Díez-González. Well-defined copper(i) complexes for Click azide–alkyne cycloaddition reactions: one Click beyond. Catalysis Science & Technology 2011, 1 (2) , 166. https://doi.org/10.1039/c0cy00064g
    26. Andrea Cadeddu, Artur Ciesielski, Tamer El Malah, Stefan Hecht, Paolo Samorì. Modulating the self-assembly of rigid “clicked” dendrimers at the solid–liquid interface by tuning non-covalent interactions between side groups. Chemical Communications 2011, 47 (38) , 10578. https://doi.org/10.1039/c1cc13099d

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