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Frustrated Helicity: Joining the Diverging Ends of a Stable Aromatic Amide Helix to Form a Fluxional Macrocycle

dc.rights.licenseopenen_US
dc.relation.isnodouble59136dac-fd43-4795-8377-68af0e599c45*
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorURUSHIBARA, Ko
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorFERRAND, Yann
dc.contributor.authorLIU, Zhiwei
dc.contributor.authorMASU, Hyuma
dc.contributor.authorPOPHRISTIC, Vojislava
dc.contributor.authorTANATANI, Aya
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorHUC, Ivan
dc.date.accessioned2020-04-08T12:47:29Z
dc.date.available2020-04-08T12:47:29Z
dc.date.issued2018
dc.identifier.issn0044-8249en_US
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/4176
dc.description.abstractEnMacrocyclization of a stable two-turn helical aromatic pentamide, that is, an object with diverging ends that are not prone to cyclization, was made possible by the transient introduction of disruptors of helicity in the form of acid-labile dimethoxybenzyl tertiary amide substituents. After removal of the helicity disruptors, NMR, X-ray crystallography, and computational studies show that the macrocycle possesses a strained structure that tries to gain as high a helical content as possible despite being cyclic. Two points of disruption of helicity remain, in particular a cis amide bond. This point of disruption of helicity can propagate along the cycle in a fluxional manner according to defined trajectories to produce ten degenerate conformations.
dc.language.isoENen_US
dc.title.enFrustrated Helicity: Joining the Diverging Ends of a Stable Aromatic Amide Helix to Form a Fluxional Macrocycle
dc.title.alternativeAngew.Chem.Int.en_US
dc.typeArticle de revueen_US
dc.identifier.doi10.1002/anie.201802159en_US
dc.subject.halChimie/Matériauxen_US
bordeaux.journalAngewandte Chemie (International ed. in English)en_US
bordeaux.page7888-7892en_US
bordeaux.volume57en_US
bordeaux.hal.laboratoriesInstitut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN) - UMR 5248
bordeaux.issue26en_US
bordeaux.institutionBordeaux INPen_US
bordeaux.institutionUniversité de Bordeauxen_US
bordeaux.peerReviewedouien_US
bordeaux.inpressnonen_US
hal.identifierhal-02536947
hal.version1
hal.date.transferred2020-04-08T12:47:34Z
hal.exporttrue
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