{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T00:51:31Z","timestamp":1760057491724,"version":"build-2065373602"},"reference-count":34,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2025,2,5]],"date-time":"2025-02-05T00:00:00Z","timestamp":1738713600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001665","name":"Agence Nationale de la Recherche","doi-asserted-by":"publisher","award":["ANR-20-CE18-0021-01"],"award-info":[{"award-number":["ANR-20-CE18-0021-01"]}],"id":[{"id":"10.13039\/501100001665","id-type":"DOI","asserted-by":"publisher"}]},{"name":"University Clermont Auvergne","award":["ANR-20-CE18-0021-01"],"award-info":[{"award-number":["ANR-20-CE18-0021-01"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This study presents a tentative synthesis of supported H-shaped and ladder-type compounds. If the ladders were not accessible, probably due to distance misfits between the reactive centers, a facile method for the synthesis of H-shaped N-alkylated aminomethyl oligobenzamides, i.e., arylopeptoids by on-resin homodimerization via the Copper(I)-Catalyzed-Alkyne-Azide-Cycloaddition (CuAAC) reaction is reported. While successful, a synthetic bottleneck was identified for further oligomer elongation due to congestion when the ligation occurs on solid support. However, this issue was effectively addressed using an elongated oligomer to conduct inter-strand cross-linking. Further CuAAC functionalization could be performed after elongation with additional alkyne groups to enhance diversity.<\/jats:p>","DOI":"10.3390\/molecules30030724","type":"journal-article","created":{"date-parts":[[2025,2,6]],"date-time":"2025-02-06T08:53:41Z","timestamp":1738832021000},"page":"724","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Clicked H-Shaped Arylopeptoids"],"prefix":"10.3390","volume":"30","author":[{"given":"Zein El Abidine","family":"Chamas","sequence":"first","affiliation":[{"name":"Universit\u00e9 Clermont Auvergne, Clermont Auvergne INP, CNRS, ICCF, F-63000 Clermont-Ferrand, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ayman","family":"Akhdar","sequence":"additional","affiliation":[{"name":"Universit\u00e9 Clermont Auvergne, Clermont Auvergne INP, CNRS, ICCF, F-63000 Clermont-Ferrand, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3540-9573","authenticated-orcid":false,"given":"Florence","family":"Charnay-Pouget","sequence":"additional","affiliation":[{"name":"Universit\u00e9 Clermont Auvergne, Clermont Auvergne INP, CNRS, ICCF, F-63000 Clermont-Ferrand, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5033-9481","authenticated-orcid":false,"given":"Sophie","family":"Faure","sequence":"additional","affiliation":[{"name":"Universit\u00e9 Clermont Auvergne, Clermont Auvergne INP, CNRS, ICCF, F-63000 Clermont-Ferrand, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Arnaud","family":"Gautier","sequence":"additional","affiliation":[{"name":"Universit\u00e9 Clermont Auvergne, Clermont Auvergne INP, CNRS, ICCF, F-63000 Clermont-Ferrand, France"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2025,2,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1002\/ejoc.200300495","article-title":"Aromatic Oligoamide Foldamers","volume":"2004","author":"Huc","year":"2004","journal-title":"Eur. J. Org. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"5271","DOI":"10.1021\/cr300116k","article-title":"Aromatic amide foldamers: Structures, properties, and functions","volume":"112","author":"Zhang","year":"2012","journal-title":"Chem. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1726","DOI":"10.1039\/b819597h","article-title":"Recent advances in the development of aryl-based foldamers","volume":"38","author":"Saraogi","year":"2009","journal-title":"Chem. Soc. Rev."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Hecht, S., and Huc, I. (2007). Foldamers: Structures, Properties and Applications, Wiley-VCH.","DOI":"10.1002\/9783527611478"},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Rinaldi, S. (2020). The Diverse World of Foldamers: Endless Possibilities of Self-Assembly. Molecules, 25.","DOI":"10.3390\/molecules25143276"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2754","DOI":"10.1002\/(SICI)1521-3773(19981102)37:20<2754::AID-ANIE2754>3.0.CO;2-3","article-title":"Polyvalent Interactions in Biological Systems: Implications for Design and Use of Multivalent Ligands and Inhibitors","volume":"37","author":"Mammen","year":"1998","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"4301","DOI":"10.1021\/acs.chemrev.9b00665","article-title":"The Staudinger Ligation","volume":"120","author":"Bednarek","year":"2020","journal-title":"Chem. 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Ed."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"3057","DOI":"10.1021\/jo011148j","article-title":"Peptidotriazoles on solid phase: [1\u20133]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides","volume":"67","author":"Christensen","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2952","DOI":"10.1021\/cr0783479","article-title":"Cu-Catalyzed Azide\u2212Alkyne Cycloaddition","volume":"108","author":"Meldal","year":"2008","journal-title":"Chem. Rev."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1325","DOI":"10.1039\/b901977b","article-title":"Tricks with clicks: Modification of peptidomimetic oligomers via copper-catalyzed azide-alkyne [3 + 2] cycloaddition","volume":"39","author":"Holub","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3365","DOI":"10.1002\/app.37662","article-title":"Application of microwave-assisted click chemistry in the preparation of functionalized copolymers for drug conjugation","volume":"127","author":"Hu","year":"2012","journal-title":"J. Appl. Polym. Sci."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"189","DOI":"10.2174\/138527211793979826","article-title":"Click chemistry under microwave or ultrasound irradiation","volume":"15","author":"Barge","year":"2011","journal-title":"Curr. Org. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1951","DOI":"10.1021\/ol050371q","article-title":"Click to Fit:\u2009 Versatile Polyvalent Display on a Peptidomimetic Scaffold","volume":"7","author":"Jang","year":"2005","journal-title":"Org. Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2315","DOI":"10.1021\/acs.bioconjchem.6b00267","article-title":"Extent of the Oxidative Side Reactions to Peptides and Proteins During the CuAAC Reaction","volume":"27","author":"Li","year":"2016","journal-title":"Bioconjugate Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"17993","DOI":"10.1021\/ja2083027","article-title":"Cellular consequences of copper complexes used to catalyze bioorthogonal click reactions","volume":"133","author":"Kennedy","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1309","DOI":"10.1002\/cbic.201100206","article-title":"Protein modification by strain-promoted alkyne-azide cycloaddition","volume":"12","year":"2011","journal-title":"ChemBioChem"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"9879","DOI":"10.1002\/anie.200905087","article-title":"Analysis and Optimization of Copper-Catalyzed Azide\u2013Alkyne Cycloaddition for Bioconjugation","volume":"48","author":"Hong","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"5852","DOI":"10.1002\/anie.201108181","article-title":"Fast, cell-compatible click chemistry with copper-chelating azides for biomolecular labeling","volume":"51","author":"Uttamapinant","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"5872","DOI":"10.1002\/anie.201310671","article-title":"Copper-Chelating Azides for Efficient Click Conjugation Reactions in Complex Media","volume":"53","author":"Bevilaqua","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"3688","DOI":"10.1021\/ja100014q","article-title":"Rapid Cu-Free Click Chemistry with Readily Synthesized Biarylazacyclooctynones","volume":"132","author":"Jewett","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"6322","DOI":"10.1002\/chem.200900727","article-title":"Improved Copper(I)\u2013NHC Catalytic Efficiency on Huisgen Reaction by Addition of Aromatic Nitrogen Donors","volume":"15","author":"Teyssot","year":"2009","journal-title":"Chem. Eur. J."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3507","DOI":"10.1002\/ejoc.201000046","article-title":"Aromatic Nitrogen Donors for Efficient Copper(I)\u2013NHC CuAAC under Reductant-Free Conditions","volume":"2010","author":"Teyssot","year":"2010","journal-title":"Eur. J. Org. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"298","DOI":"10.1002\/cplu.202000825","article-title":"N-Alkylated Aromatic Poly- and Oligoamides","volume":"86","author":"Akhdar","year":"2021","journal-title":"ChemPlusChem"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2402","DOI":"10.1039\/D2OB00163B","article-title":"Arylopeptoid oligomers functionalised by combinatorial or sequential on-resin click chemistry using a copper(I)\u2013N-heterocyclic carbene catalyst","volume":"20","author":"Akhdar","year":"2022","journal-title":"Org. Biomol. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2215","DOI":"10.1002\/anie.200461656","article-title":"Head-to-tail peptide cyclodimerization by copper-catalyzed azide-alkyne cycloaddition","volume":"44","author":"Punna","year":"2005","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"3275","DOI":"10.1021\/ol071169l","article-title":"Fit to Be Tied:\u2009 Conformation-Directed Macrocyclization of Peptoid Foldamers","volume":"9","author":"Holub","year":"2007","journal-title":"Org. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"4005","DOI":"10.1039\/c2cc30515a","article-title":"A water-soluble CuI\u2013NHC for CuAAC ligation of unprotected peptides under open air conditions","volume":"48","author":"Gaulier","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"13515","DOI":"10.1021\/acs.joc.8b01490","article-title":"Use of an Air-Stable Cu(I)-NHC Catalyst for the Synthesis of Peptidotriazoles","volume":"83","author":"Bruyat","year":"2018","journal-title":"J. Org. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"8087","DOI":"10.1039\/D3CC01956J","article-title":"Cage-like structures based on constrained cyclic arylopeptoids","volume":"59","author":"Akhdar","year":"2023","journal-title":"Chem. 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