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dc.rights.licenseopenen_US
dc.contributor.authorPULKA-ZIACH, Karolina
dc.contributor.authorANTUNES, Stephanie
dc.contributor.authorPERDRIAU, Camille
dc.contributor.authorKAUFFMANN, Brice
dc.contributor.authorPASCO, Morgane
IDREF: 152520791
dc.contributor.authorDOUAT, Celine
dc.contributor.authorGUICHARD, Gilles
IDREF: 084339268
dc.date.accessioned2020-03-26T16:50:32Z
dc.date.available2020-03-26T16:50:32Z
dc.date.issued2018
dc.identifier.issn0022-3263en_US
dc.identifier.other10.1021/acs.joc.7b01895en_US
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/3947
dc.description.abstractEnThe synthesis of hybrid urea-based foldamers containing isosteric guanidinium linkages at selected positions in the sequence is described. We used a postelongation approach whereby the guanidinium moiety is introduced by direct transformation of a parent oligo(urea/thiourea) foldamer precursor. The method involves activation of the thiourea by treatment with methyl iodide and subsequent reaction with amines. To avoid undesired cyclization with the preceding urea moiety, resulting in heterocyclic guanidinium formation in the main chain, the urea unit preceding the thiourea unit in the sequence was replaced by an isoatomic and isostructural gamma-amino acid. The approach was extended to solid-phase techniques to accelerate the synthesis of longer and more functionalized sequences. Under optimized conditions, an octamer hybrid oligomer incorporating a central guanidinium linkage was obtained in good overall yield and purity. This work also reports data related to the structural consequences of urea by guanidinium replacements in solution and reveals that helical folding is substantially reduced in oligomers containing a guanidinium group.
dc.language.isoENen_US
dc.subject.enGuanidine
dc.subject.enUrea
dc.subject.enOligomers
dc.subject.enMixtures
dc.subject.enSolvents
dc.title.enPostelongation Strategy for the Introduction of Guanidinium Units in the Main Chain of Helical Oligourea Foldamers
dc.typeArticle de revueen_US
dc.identifier.doi10.1021/acs.joc.7b01895
dc.subject.halChimie/Matériauxen_US
bordeaux.journalThe Journal of organic chemistryen_US
bordeaux.page2530-2541en_US
bordeaux.volume83en_US
bordeaux.hal.laboratoriesInstitut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN) - UMR 5248
bordeaux.issue5en_US
bordeaux.institutionBordeaux INPen_US
bordeaux.institutionUniversité de Bordeauxen_US
bordeaux.peerReviewedouien_US
bordeaux.inpressnonen_US
hal.identifierhal-03184416
hal.version1
hal.date.transferred2021-03-29T12:30:10Z
hal.exporttrue
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