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Assessing Interactions between Helical Aromatic Oligoamide Foldamers and Protein Surfaces: A Tethering Approach

dc.rights.licenseopenen_US
dc.relation.isnodouble1cce0408-ac0e-4cbf-a3bd-8ec71b4b3456*
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorVALLADE, MaeIle
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorJEWGINSKI, Michal
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorFISCHER DUROLA, Lucile
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorBURATTO, Jeremie
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorBATHANY, Katell
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorSCHMITTER, Jean-Marie
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorSTUPFEL, Marine
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorGODDE, Frederic
hal.structure.identifierAcides Nucléiques : Régulations Naturelle et Artificielle [ARNA]
dc.contributor.authorMACKERETH, Cameron D.
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorHUC, Ivan
dc.date.accessioned2020-04-22T09:55:43Z
dc.date.available2020-04-22T09:55:43Z
dc.date.issued2019
dc.identifier.issn1043-1802en_US
dc.identifier.other10.1021/acs.bioconjchem.8b00710en_US
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/4335
dc.description.abstractEnHelically folded aromatic foldamers may constitute suitable candidates for the ab initio design of ligands for protein surfaces. As preliminary steps toward the exploration of this hypothesis, a tethering approach was developed to detect interactions between a protein and a foldamer by confining the former at the surface of the latter. Cysteine mutants of two therapeutically relevant enzymes, CypA and IL4, were produced. Two series of ten foldamers were synthesized bearing different proteinogenic side chains and either a long or a short linker functionalized with an activated disulfide. Disulfide exchange between the mutated cysteines and the activated disulfides yielded 20 foldamer-IL4 and 20 foldamer-CypA adducts. Effectiveness of the reaction was demonstrated by LC-MS, by MS analysis after proteolytic digestion, and by 2D NMR. Circular dichroism then revealed diastereoselective interactions between the proteins and the foldamers confined at their surface which resulted in a preferred handedness of the foldamer helix. Helix sense bias occurred sometimes with both the short and the long linkers and sometimes with only one of them. In a few cases, helix handedness preference is found to be close to quantitative. These cases constitute valid candidates for structural elucidation of the interactions involved.
dc.language.isoENen_US
dc.subject.enDisulfides
dc.subject.enFoldamers
dc.subject.enPeptides and proteins
dc.subject.enSurface interactions
dc.subject.enMonomers
dc.title.enAssessing Interactions between Helical Aromatic Oligoamide Foldamers and Protein Surfaces: A Tethering Approach
dc.typeArticle de revueen_US
dc.identifier.doi10.1021/acs.bioconjchem.8b00710
dc.subject.halChimie/Matériauxen_US
bordeaux.journalBioconjugate Chemistryen_US
bordeaux.page54-62en_US
bordeaux.volume30en_US
bordeaux.hal.laboratoriesInstitut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN) - UMR 5248en_US
bordeaux.issue1en_US
bordeaux.institutionBordeaux INPen_US
bordeaux.institutionUniversité de Bordeauxen_US
bordeaux.peerReviewedouien_US
bordeaux.inpressnonen_US
hal.identifierhal-03182221
hal.version1
hal.date.transferred2021-03-26T10:09:10Z
hal.exporttrue
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