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Primary Structure Control of Oligomers Based on Natural and Synthetic Building Blocks

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Institut Charles Sadron, UPR22/CNRS, 23 rue du Loess, BP 84047, 67034 Strasbourg Cedex 2, France
Cite this: ACS Macro Lett. 2014, 3, 3, 291–294
Publication Date (Web):March 10, 2014
https://doi.org/10.1021/mz5000575
Copyright © 2014 American Chemical Society

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    Abstract

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    Solid-phase synthesis was exploited for the preparation of oligomers constructed from natural and synthetic building blocks by combining the formation of amide bonds and copper-assisted alkyne–azide cycloaddition reactions extending the variety of oligomers with well-defined primary structures accessible through this technique and providing control over the spacing between amino acids.

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    Experimental section describing the procedure and characterization details for the synthesis of azidocarboxylic acids, azidoamino acids, azidopeptides, and sequence-defined oligomers based on natural and synthetic building blocks and Figures S1–S5. This material is available free of charge via the Internet at http://pubs.acs.org.

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    2. Delphine Chan-Seng Jean-François Lutz . Solid-Phase Synthesis as a Tool for the Preparation of Sequence-Defined Oligomers Based on Natural Amino Acids and Synthetic Building Blocks. 2014, 103-116. https://doi.org/10.1021/bk-2014-1170.ch007
    3. Yuxi Long, Meiting Ma, Yinuo Wang, Chenyang Zheng, Shudan Ye, Jiachang Huang, Benzhao He. Sequence-controlled polymers constructed by alkyne-based polymerizations. Giant 2023, 15 , 100168. https://doi.org/10.1016/j.giant.2023.100168
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    7. Jeroen Louwsma, Alain Carvalho, Jean-François Lutz, Stéphane Joly, Delphine Chan-Seng. Adsorption of phenylalanine-rich sequence-defined oligomers onto Kevlar fibers for fiber-reinforced polyolefin composite materials. Polymer 2021, 217 , 123465. https://doi.org/10.1016/j.polymer.2021.123465
    8. Bas Genabeek, Brigitte A. G. Lamers, Craig J. Hawker, E. W. Meijer, Will R. Gutekunst, Bernhard V. K. J. Schmidt. Properties and applications of precision oligomer materials; where organic and polymer chemistry join forces. Journal of Polymer Science 2021, 59 (5) , 373-403. https://doi.org/10.1002/pol.20200862
    9. Pandurangan Nanjan, Mintu Porel. Sequence-defined non-natural polymers: synthesis and applications. Polymer Chemistry 2019, 10 (40) , 5406-5424. https://doi.org/10.1039/C9PY00886A
    10. Cangjie Yang, James P. Flynn, Jia Niu. Facile Synthesis of Sequence‐Regulated Synthetic Polymers Using Orthogonal SuFEx and CuAAC Click Reactions. Angewandte Chemie 2018, 130 (49) , 16426-16431. https://doi.org/10.1002/ange.201811051
    11. Cangjie Yang, James P. Flynn, Jia Niu. Facile Synthesis of Sequence‐Regulated Synthetic Polymers Using Orthogonal SuFEx and CuAAC Click Reactions. Angewandte Chemie International Edition 2018, 57 (49) , 16194-16199. https://doi.org/10.1002/anie.201811051
    12. Delphine Chan‐Seng, Jeroen Louwsma, Jean‐François Lutz, Stéphane Joly. Synthesis of Macromolecules Containing Phenylalanine and Aliphatic Building Blocks. Macromolecular Rapid Communications 2018, 39 (8) https://doi.org/10.1002/marc.201700764
    13. Steven Martens, Joshua O. Holloway, Filip E. Du Prez. Click and Click‐Inspired Chemistry for the Design of Sequence‐Controlled Polymers. 2018, 379-416. https://doi.org/10.1002/9783527806096.ch13
    14. Steven Martens, Joshua O. Holloway, Filip. E. Du Prez. Click and Click‐Inspired Chemistry for the Design of Sequence‐Controlled Polymers. Macromolecular Rapid Communications 2017, 38 (24) https://doi.org/10.1002/marc.201700469
    15. Abdelaziz Al Ouahabi, Raj Kumar Roy, Jean-François Lutz. Synthesis of Non-natural Polymers with Controlled Primary Structures. 2016, 66-106. https://doi.org/10.1039/9781782626664-00066
    16. Joke Vandenbergh, Gunter Reekmans, Peter Adriaensens, Tanja Junkers. Synthesis of sequence-defined acrylate oligomers via photo-induced copper-mediated radical monomer insertions. Chemical Science 2015, 6 (10) , 5753-5761. https://doi.org/10.1039/C5SC02035B
    17. Khoubaib Ben Haj Salah, Baptiste Legrand, Sanjit Das, Jean Martinez, Nicolas Inguimbert. Straightforward strategy to substitute amide bonds by 1,2,3‐triazoles in peptaibols analogs using Aibψ[Tz]‐Xaa dipeptides. Peptide Science 2015, 104 (5) , 611-621. https://doi.org/10.1002/bip.22641
    18. Bhanu P. Mudraboyina, Mona M. Obadia, Imen Abdelhedi-Miladi, Imène Allaoua, Eric Drockenmuller. Versatile click functionalization of poly(1,2,3-triazolium ionic liquid)s. European Polymer Journal 2015, 62 , 331-337. https://doi.org/10.1016/j.eurpolymj.2014.08.025

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