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Polar solvent effects on tartaric acid binding by aromatic oligoamide foldamer capsules

dc.contributor.authorCHANDRAMOULI, Nagula
dc.contributor.authorEL-BEHAIRY, Mohammed Farrag
dc.contributor.authorLAUTRETTE, Guillaume
dc.contributor.authorFERRAND, Yann
dc.contributor.authorHUC, Ivan
dc.date.accessioned2020-09-03T07:56:25Z
dc.date.available2020-09-03T07:56:25Z
dc.date.issued2016
dc.identifier.issn1477-0520
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/10895
dc.description.abstractEnAromatic oligoamide sequences able to fold into single helical capsules were functionalized with two types of side chains to make them soluble in various solvents such as chloroform, methanol or water and their propensity to recognize tartaric acid was evaluated. The binding affinities to tartaric acid and binding thermodynamics in different media were investigated by variable temperature H-1 NMR and ITC experiments, the two methods giving consistent results. We show that tartaric acid binding mainly rests on enthalpically favourable polar interactions that were found to be sufficiently strong to be effective in the presence of a polar aprotic solvent (DMSO) and even in pure methanol. Binding in water was very weak. The stronger binding interactions were found to be more susceptible to the effect of competitive solvents and compensated by unfavourable entropic effects. Thus, the best host in a less polar medium eventually was found to be the worst host in protic solvents. An interesting case of entropically driven binding was evidenced in methanol.
dc.language.isoen
dc.title.enPolar solvent effects on tartaric acid binding by aromatic oligoamide foldamer capsules
dc.typeArticle de revue
dc.identifier.doi10.1039/c5ob02641e
dc.subject.halChimie/Matériaux
bordeaux.journalOrganic & Biomolecular Chemistry
bordeaux.page2466-2472
bordeaux.volume14
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.issue8
bordeaux.institutionUniversité de Bordeaux
bordeaux.institutionBordeaux INP
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Organic%20&%20Biomolecular%20Chemistry&rft.date=2016&rft.volume=14&rft.issue=8&rft.spage=2466-2472&rft.epage=2466-2472&rft.eissn=1477-0520&rft.issn=1477-0520&rft.au=CHANDRAMOULI,%20Nagula&EL-BEHAIRY,%20Mohammed%20Farrag&LAUTRETTE,%20Guillaume&FERRAND,%20Yann&HUC,%20Ivan&rft.genre=article


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