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Isosteric substitutions of urea to thiourea and selenourea in aliphatic oligourea foldamers: site-specific perturbation of the helix geometry

dc.contributor.authorNELLI, Yella Reddy
dc.contributor.authorANTUNES, Stephanie
dc.contributor.authorSALAUN, Arnaud
dc.contributor.authorTHINON, Emmanuelle
dc.contributor.authorMASSIP, Stephane
dc.contributor.authorKAUFFMANN, Brice
dc.contributor.authorDOUAT, Celine
dc.contributor.authorGUICHARD, Gilles
IDREF: 084339268
dc.date.accessioned2020-09-03T08:01:59Z
dc.date.available2020-09-03T08:01:59Z
dc.date.issued2015
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/10945
dc.description.abstractEnNearly isosteric oxo to thioxo substitution was employed to interrogate the structure of foldamers with a urea backbone and explore the relationship between helical folding and hydrogen-bonding interactions. A series of oligomers with urea bonds substituted by thiourea bonds at discrete or all positions in the sequence have been prepared and their folding propensity was studied by using a combination of spectroscopic methods and X-ray diffraction. The outcome of oxo to thioxo replacements on the helical folding was found to depend on whether central or terminal ureas were modified. The canonical helix geometry was not affected upon insertion of thioureas close to the negative end of the helix dipole, whereas thioureas close to the positive pole were found to increase the terminal flexibility and cause helix fraying. Perturbation was amplified when a selenourea was incorporated instead, leading to a structure that is only partly folded.
dc.language.isoen
dc.title.enIsosteric substitutions of urea to thiourea and selenourea in aliphatic oligourea foldamers: site-specific perturbation of the helix geometry
dc.typeArticle de revue
dc.identifier.doi10.1002/chem.201405792
dc.subject.halChimie/Matériaux
bordeaux.journalChemistry (Weinheim an der Bergstrasse, Germany)
bordeaux.page2870-80
bordeaux.volume21
bordeaux.hal.laboratoriesInstitut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN) - UMR 5248*
bordeaux.hal.laboratoriesInstitut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN, UMR 5248)
bordeaux.issue7
bordeaux.institutionUniversité de Bordeaux
bordeaux.institutionBordeaux INP
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Chemistry%20(Weinheim%20an%20der%20Bergstrasse,%20Germany)&rft.date=2015&rft.volume=21&rft.issue=7&rft.spage=2870-80&rft.epage=2870-80&rft.au=NELLI,%20Yella%20Reddy&ANTUNES,%20Stephanie&SALAUN,%20Arnaud&THINON,%20Emmanuelle&MASSIP,%20Stephane&rft.genre=article


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