{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T09:22:10Z","timestamp":1789204930045,"version":"build-2803163510"},"reference-count":54,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2019,3,26]],"date-time":"2019-03-26T00:00:00Z","timestamp":1553558400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["SE 609\/10-1"],"award-info":[{"award-number":["SE 609\/10-1"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["SFB 749"],"award-info":[{"award-number":["SFB 749"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["project C8"],"award-info":[{"award-number":["project C8"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["CIPSM"],"award-info":[{"award-number":["CIPSM"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001655","name":"Deutscher Akademischer Austauschdienst","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001655","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008648","name":"Krajowy Naukowy Osrodek Wiodacy","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100008648","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002347","name":"Bundesministerium f\u00fcr Bildung und Forschung","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100002347","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Chem."],"DOI":"10.3389\/fchem.2019.00155","type":"journal-article","created":{"date-parts":[[2019,3,26]],"date-time":"2019-03-26T05:04:15Z","timestamp":1553576655000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":23,"title":["1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties"],"prefix":"10.3389","volume":"7","author":[{"given":"David C.","family":"Schr\u00f6der","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oliver","family":"Kracker","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tanja","family":"Fr\u00f6hr","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jerzy","family":"G\u00f3ra","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Micha\u0142","family":"Jewginski","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anke","family":"Nie\u00df","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Iris","family":"Antes","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rafa\u0142","family":"Latajka","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Antoine","family":"Marion","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Norbert","family":"Sewald","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1965","published-online":{"date-parts":[[2019,3,26]]},"reference":[{"key":"B1","doi-asserted-by":"crossref","first-page":"230","DOI":"10.1006\/jmra.1996.0199","article-title":"Evaluation of distances from ROESY experiments with the intensity-ratiomethod","volume":"122","author":"\u00c4mm\u00e4lahti","year":"1996","journal-title":"J. Magn. Reson. Ser. A"},{"key":"B2","doi-asserted-by":"publisher","first-page":"9595","DOI":"10.1021\/jo0516180","article-title":"Ring closure to \u03b2-turn mimics via copper-catalyzed azide\/alkynecycloadditions","volume":"70","author":"Angell","year":"2005","journal-title":"J. Org. Chem."},{"key":"B3","doi-asserted-by":"publisher","first-page":"1674","DOI":"10.1039\/b701444a","article-title":"Peptidomimetics via copper-catalyzed azide-alkynecycloadditions","volume":"36","author":"Angell","year":"2007","journal-title":"Chem. Soc. Rev."},{"key":"B4","doi-asserted-by":"publisher","first-page":"17134","DOI":"10.1021\/ja056406z","article-title":"Nonpeptidic foldamers from amino acids: synthesis and characterization of 1,3-substituted triazole oligomers","volume":"127","author":"Angelo","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"B5","doi-asserted-by":"publisher","first-page":"7963","DOI":"10.1021\/jo701292h","article-title":"Solution- and solid-phase synthesis of triazole oligomers that display protein-likefunctionality","volume":"72","author":"Angelo","year":"2007","journal-title":"J. Org. Chem."},{"key":"B6","doi-asserted-by":"publisher","first-page":"9312","DOI":"10.1002\/anie.200703590","article-title":"The 1,2,3-triazole ring as a peptido- and olefinomimetic element: discovery of click vanilloids and cannabinoids","volume":"46","author":"Appendino","year":"2007","journal-title":"Angew. Chem. Int. Ed."},{"key":"B7","doi-asserted-by":"publisher","first-page":"9","DOI":"10.3762\/bjoc.7.2","article-title":"Thermal rearrangement of tert-butylsulfinamide","volume":"7","author":"Arava","year":"2011","journal-title":"Beilstein J. Org. Chem."},{"key":"B8","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1021\/ol0621506","article-title":"One-pot procedure for diazo transfer and azide-alkyne cycloaddition: triazole linkages fromamines","volume":"9","author":"Beckmann","year":"2007","journal-title":"Org. Lett."},{"key":"B9","doi-asserted-by":"publisher","first-page":"4725","DOI":"10.1002\/anie.200805901","article-title":"Conformationally homogeneous heterocyclic pseudotetrapeptides as three-dimensional scaffolds for rational drug design: receptor-selective somatostatin analogues","volume":"48","author":"Beierle","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"B10","doi-asserted-by":"publisher","first-page":"611","DOI":"10.1002\/bip.22641","article-title":"Straightforward strategy to substitute amide bonds by 1,2,3-triazoles in peptaibols analogs using Aib\u03c8[Tz]-Xaadipeptide","volume":"104","author":"Ben Haj Salah","year":"2015","journal-title":"Biopolymers"},{"key":"B11","doi-asserted-by":"publisher","first-page":"3576","DOI":"10.1039\/C8OB00686E","article-title":"How are 1,2,3-triazoles accommodated in helical secondary structures?","volume":"16","author":"Ben Haj Salah","year":"2018","journal-title":"Org. Biomol. Chem."},{"key":"B12","doi-asserted-by":"publisher","first-page":"51","DOI":"10.1002\/ejoc.200500483","article-title":"CuI-catalyzed alkyne\u2013azide \u201cClick\u201d Cycloadditions from a mechanistic and synthetic perspective","volume":"1","author":"Bock","year":"","journal-title":"Eur. J. Org. Chem."},{"key":"B13","doi-asserted-by":"publisher","first-page":"919","DOI":"10.1021\/ol053095o","article-title":"Click chemistry as a route to cyclic tetrapeptide analogues: synthesis of cyclo-[Pro-Val-\u03c8(triazole)-Pro-Tyr]","volume":"8","author":"Bock","year":"","journal-title":"Org. Lett."},{"key":"B14","doi-asserted-by":"publisher","first-page":"971","DOI":"10.1039\/b616751a","article-title":"1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptidemimics","volume":"5","author":"Bock","year":"2007","journal-title":"Org. Biomol. Chem."},{"key":"B15","doi-asserted-by":"publisher","first-page":"1167","DOI":"10.1002\/cbic.200500101","article-title":"1,2,3-triazole as a peptide surrogate in the rapid synthesis of HIV-1 proteaseinhibitors","volume":"6","author":"Brik","year":"2005","journal-title":"Chem. Bio. Chem"},{"key":"B16","doi-asserted-by":"publisher","first-page":"1246","DOI":"10.1002\/cbic.200300724","article-title":"Rapid diversity-oriented synthesis in microtiter plates for in situ screening of HIV proteaseinhibitors","volume":"4","author":"Brik","year":"2003","journal-title":"Chem. Bio. Chem"},{"key":"B17","volume-title":"AMBER","author":"Case","year":"2017"},{"key":"B18","doi-asserted-by":"publisher","first-page":"769","DOI":"10.1021\/cb9001415","article-title":"Bivalent peptidomimetic ligands of TrkC are biased agonists and selectively induce neuritogenesis or potentiate neurotrophin-3 trophicsignals","volume":"4","author":"Chen","year":"2009","journal-title":"ACS Chem. Biol."},{"key":"B19","doi-asserted-by":"publisher","first-page":"8070","DOI":"10.1021\/jp9717655","article-title":"Application of the RESP methodology in the parametrization of organicsolvents","volume":"102","author":"Fox","year":"1998","journal-title":"J. Phys. Chem. B"},{"key":"B20","doi-asserted-by":"publisher","first-page":"1589","DOI":"10.1002\/chin.200735250","article-title":"Click chemistry - what's in a name? triazole synthesis and beyond","volume":"11","author":"Gil","year":"2007","journal-title":"Synthesis"},{"key":"B21","doi-asserted-by":"publisher","first-page":"7512","DOI":"10.1021\/jo971176v","article-title":"NMR chemical shifts of common laboratory solvents as trace impurities","volume":"62","author":"Gottlieb","year":"1997","journal-title":"J. Org. Chem."},{"key":"B22","doi-asserted-by":"publisher","first-page":"242","DOI":"10.1021\/ma902018w","article-title":"Polypseudopeptides with variable stereochemistry: synthesis via click-chemistry, postfunctionalization and conformational behavior in solution","volume":"43","author":"Hartwig","year":"2010","journal-title":"Macromolecules"},{"key":"B23","doi-asserted-by":"publisher","first-page":"2216","DOI":"10.1007\/s11095-008-9616-1","article-title":"Click chemistry, a powerful tool for pharmaceutical sciences","volume":"25","author":"Hein","year":"2008","journal-title":"Pharm. Res."},{"key":"B24","doi-asserted-by":"publisher","first-page":"9665","DOI":"10.1063\/1.1683075","article-title":"Development of an improved four-site water model for biomolecular simulations: TIP4P-Ew, J","volume":"120","author":"Horn","year":"2004","journal-title":"Chem. Phys."},{"key":"B25","doi-asserted-by":"publisher","first-page":"4718","DOI":"10.1002\/anie.200805900","article-title":"Probing the bioactive conformation of an archetypal natural product HDAC inhibitor with conformationally homogeneous triazole-modified cyclictetrapeptides","volume":"48","author":"Horne","year":"2009","journal-title":"Angew. Chem. Int. Ed"},{"key":"B26","doi-asserted-by":"publisher","first-page":"15366","DOI":"10.1021\/ja0450408","article-title":"Heterocyclic peptide backbone modifications in an alpha-helical coiled coil","volume":"126","author":"Horne","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"B27","doi-asserted-by":"publisher","first-page":"33","DOI":"10.1016\/0263-7855(96)00018-5","article-title":"VMD: visual molecular dynamics","volume":"14","author":"Humphrey","year":"1996","journal-title":"J. Molec. Graph"},{"key":"B28","doi-asserted-by":"publisher","first-page":"90","DOI":"10.1109\/MCSE.2007.55","article-title":"Matplotlib: A 2D Graphics Environment","volume":"9","author":"Hunter","year":"2007","journal-title":"Comput. Sci. Eng."},{"key":"B29","doi-asserted-by":"publisher","first-page":"6023","DOI":"10.1016\/j.bmcl.2009.09.049","article-title":"Evaluation of triazolamers as active site inhibitors of HIV-1protease","volume":"19","author":"Jochim","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"B30","doi-asserted-by":"publisher","first-page":"394","DOI":"10.1021\/ol2031685","article-title":"Head-to-tail dimerization and organogelating properties of click peptidomimetics. Org. Lett","volume":"14","author":"Ke","year":"2012"},{"key":"B31","doi-asserted-by":"publisher","first-page":"4584","DOI":"10.1016\/j.bmcl.2007.05.086","article-title":"Design, synthesis, and preliminary biological evaluation of a novel triazole analogue of ceramide","volume":"17","author":"Kim","year":"2007","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"B32","doi-asserted-by":"publisher","first-page":"1128","DOI":"10.1016\/S1359-6446(03)02933-7","article-title":"The growing impact of click chemistry on drug discovery","volume":"8","author":"Kolb","year":"2003","journal-title":"Drug Disc. Today"},{"key":"B33","doi-asserted-by":"publisher","first-page":"953","DOI":"10.1002\/chem.201704583","article-title":"1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles For A Class Of Versatilepeptidomimetics","volume":"24","author":"Kracker","year":"2018","journal-title":"Chem. Eur. J."},{"key":"B34","doi-asserted-by":"publisher","first-page":"585","DOI":"10.1021\/jm061243q","article-title":"Synthesis and evaluation of 1,2,3-triazole containing analogues of the immunostimulant alpha-GalCer. J","volume":"50","author":"Lee","year":"2007","journal-title":"Med. Chem."},{"key":"B35","doi-asserted-by":"publisher","first-page":"303","DOI":"10.1021\/ol9912480","article-title":"Traceless solid-phase synthesis of chiral 3-aryl \u03b2-amino acid containing peptides using a side-chain-tethered \u03b2-amino acid building block","volume":"2","author":"Lee","year":"2000","journal-title":"Org. Lett."},{"key":"B36","doi-asserted-by":"publisher","first-page":"90","DOI":"10.1021\/acs.jcim.7b00305","article-title":"Amber-compatible parametrization procedure for peptide-like compounds: application to 1,4- and 1,5-substituted triazole-basedpeptidomimetics","volume":"58","author":"Marion","year":"2018","journal-title":"J. Chem. Inf. Model"},{"key":"B37","doi-asserted-by":"publisher","first-page":"1249","DOI":"10.1039\/B613014N","article-title":"The growing applications of clickchemistry","volume":"36","author":"Moses","year":"2007","journal-title":"Chem. Soc. Rev."},{"key":"B38","doi-asserted-by":"publisher","first-page":"1064","DOI":"10.1021\/ol1000473","article-title":"\u201cClicktophycin-52\u201d: a bioactive cryptophycin-52 triazoleanalogue","volume":"12","author":"Nahrwold","year":"2010","journal-title":"Org. Lett."},{"key":"B39","doi-asserted-by":"publisher","first-page":"289","DOI":"10.1089\/cbr.2008.0626","article-title":"Growing applications of \u201cclick chemistry\u201d for bioconjugation in contemporary biomedicalresearch","volume":"24","author":"Nwe","year":"2009","journal-title":"Cancer Biother. Radiopharm."},{"key":"B40","unstructured":"OliphantT. E.\n          A guide toNumPy, USA: Trelgol Publishing 20062007"},{"key":"B41","doi-asserted-by":"publisher","first-page":"7110","DOI":"10.1021\/jo061160h","article-title":"Asymmetric synthesis of \u03b1,\u03b1-dibranched propargylamines by acetylide additions to N-tert-butanesulfinylketimines","volume":"71","author":"Patterson","year":"2006","journal-title":"J. Org. Chem."},{"key":"B42","doi-asserted-by":"publisher","first-page":"2399","DOI":"10.1002\/ejoc.201100157","article-title":"1,2,3-triazoles in peptidomimetic chemistry","volume":"2011","author":"Pedersen","year":"2011","journal-title":"Eur. J. Org. Chem."},{"key":"B43","doi-asserted-by":"publisher","first-page":"3084","DOI":"10.1021\/ct400341p","article-title":"PTRAJ and CPPTRAJ: software for processing and analysis of molecular dynamics trajectory data","volume":"9","author":"Roe","year":"2013","journal-title":"J. Chem. Theory Comput"},{"key":"B44","doi-asserted-by":"publisher","first-page":"2596","DOI":"10.1002\/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4","article-title":"A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective \u201cligation\u201d of azides and terminalalkynes","volume":"41","author":"Rostovtsev","year":"2002","journal-title":"Angew. Chem. Int. Ed."},{"key":"B45","doi-asserted-by":"publisher","first-page":"10672","DOI":"10.1021\/ja00052a093","article-title":"Design,synthesis, and crystal structure of a pyrrolinone-based peptidomimetic possessing the conformation of a \u03b2-strand: potential application to the design of novel inhibitors of proteolytic enzymes","volume":"114","author":"Smith","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"B46","doi-asserted-by":"publisher","first-page":"3057","DOI":"10.1021\/jo011148j","article-title":"Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes toazides","volume":"67","author":"Torn\u00f8e","year":"2002","journal-title":"J. Org. Chem"},{"key":"B47","doi-asserted-by":"publisher","first-page":"278","DOI":"10.1002\/med.20107","article-title":"Click chemistry reactions in medicinal chemistry: Applications of the 1,3-dipolar cycloaddition between azides andalkynes","volume":"28","author":"Tron","year":"2008","journal-title":"Med. Res. Rev."},{"key":"B48","doi-asserted-by":"publisher","first-page":"7475","DOI":"10.1021\/acs.jmedchem.5b00994","article-title":"Probing the backbone function of tumor targeting peptides by an amide-to-triazole substitution strategy","volume":"58","author":"Valverde","year":"2015","journal-title":"J. Med. Chem"},{"key":"B49","doi-asserted-by":"publisher","first-page":"4503","DOI":"10.1021\/ol0518028","article-title":"Efficient Route to C2 Symmetric Heterocyclic Backbone Modified CyclicPeptides","volume":"7","author":"van Maarseveen","year":"2005","journal-title":"Org. Lett."},{"key":"B50","doi-asserted-by":"publisher","first-page":"3821","DOI":"10.1021\/ol061431a","article-title":"Rapid assembly of matrix metalloprotease inhibitors using clickchemistry","volume":"8","author":"Wang","year":"2006","journal-title":"Org. Lett."},{"key":"B51","doi-asserted-by":"publisher","first-page":"157","DOI":"10.15227\/orgsyn.082.0157","article-title":"(RS)-(+)-2-Methyl-2-propanesulfinamide","volume":"82","author":"Weix","year":"2005","journal-title":"Org. Synth."},{"key":"B52","doi-asserted-by":"publisher","first-page":"2428","DOI":"10.3762\/bjoc.13.240","article-title":"Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics","volume":"13","author":"W\u00fcnsch","year":"2017","journal-title":"Beilstein J. Org. Chem."},{"key":"B53","doi-asserted-by":"publisher","first-page":"8993","DOI":"10.1016\/j.tetlet.2005.10.103","article-title":"An efficient and improved procedure for preparation of triflyl azide and application in catalytic diazotransferreaction","volume":"46","author":"Yan","year":"2005","journal-title":"Tetrahedron Lett"},{"key":"B54","doi-asserted-by":"publisher","first-page":"15998","DOI":"10.1021\/ja054114s","article-title":"Ruthenium-catalyzed cycloaddition of alkynes and organicazides","volume":"127","author":"Zhang","year":"2005","journal-title":"J. Am. Chem. Soc."}],"container-title":["Frontiers in Chemistry"],"original-title":[],"link":[{"URL":"https:\/\/www.frontiersin.org\/article\/10.3389\/fchem.2019.00155\/full","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2019,3,26]],"date-time":"2019-03-26T05:04:25Z","timestamp":1553576665000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.frontiersin.org\/article\/10.3389\/fchem.2019.00155\/full"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,3,26]]},"references-count":54,"alternative-id":["10.3389\/fchem.2019.00155"],"URL":"https:\/\/doi.org\/10.3389\/fchem.2019.00155","relation":{},"ISSN":["2296-2646"],"issn-type":[{"value":"2296-2646","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,3,26]]},"article-number":"155"}}