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Optimizing side chains for crystal growth from water: a case study of aromatic amide foldamers

dc.relation.isnodoublea0103107-8b4f-45d3-8dbb-dc8fa3328bd8*
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorHU, Xiaobo
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorDAWSON, Simon J.
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorMANDAL, Pradeep K.
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorDE HATTEN, Xavier
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorBAPTISTE, Benoit
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorHUC, Ivan
dc.date.accessioned2020-07-09T14:16:50Z
dc.date.available2020-07-09T14:16:50Z
dc.date.issued2017-05
dc.identifier.issn2041-6520
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/10311
dc.description.abstractEnThe growth of crystals of aromatic compounds from water much depends on the nature of the water solubilizing functions that they carry. Rationalizing crystallization from water, and structure elucidation, of aromatic molecular and supramolecular systems is of general value across various fields of chemistry. Taking helical aromatic foldamers as a test case, we have validated several short polar side chains as efficient substituents to provide both solubility in, and crystal growth ability from, water. New 8-amino-2-quinolinecarboxylic acids bearing charged or neutral aminomethyl, carboxymethyl, sulfonic acid, or bis(hydroxymethyl)-methoxy side chains in position 4 or 5, were prepared on a multi gram scale. Fmoc protection of the main chain amine and suitable protections of the side chains ensured compatibility with solid phase synthesis. One tetrameric and five octameric oligoamides displaying these side chains were synthesized and shown to be soluble in water. In all cases but one, crystals were obtained using the hanging drop method, thus validating the initial design principle to combine polarity and rigidity. The only case that resisted crystallization appeared to be due to exceedingly high water solubility endowed by eight sulfonic acid functions. The neutral side chain did provide crystal growth ability from water but contributed poorly to solubility.
dc.title.enOptimizing side chains for crystal growth from water: a case study of aromatic amide foldamers
dc.typeArticle de revue
dc.identifier.doi10.1039/c7sc00430c
dc.subject.halChimie/Matériaux
bordeaux.journalChemical Science
bordeaux.page3741-3749
bordeaux.volume8
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.issue5
bordeaux.institutionUniversité de Bordeaux
bordeaux.institutionBordeaux INP
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