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Iterative design of a helically folded aromatic oligoamide sequence for the selective encapsulation of fructose

dc.contributor.authorCHANDRAMOULI, Nagula
dc.contributor.authorFERRAND, Yann
dc.contributor.authorLAUTRETTE, Guillaume
dc.contributor.authorKAUFFMANN, Brice
dc.contributor.authorMACKERETH, Cameron David
dc.contributor.authorLAGUERRE, Michel
dc.contributor.authorDUBREUIL, Didier
dc.contributor.authorHUC, Ivan
dc.date.accessioned2020-09-03T08:02:16Z
dc.date.available2020-09-03T08:02:16Z
dc.date.issued2015
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/11003
dc.description.abstractEnThe ab initio design of synthetic molecular receptors for a specific biomolecular guest remains an elusive objective, particularly for targets such as monosaccharides, which have very close structural analogues. Here we report a powerful approach to produce receptors with very high selectivity for specific monosaccharides and, as a demonstration, we develop a foldamer that selectively encapsulates fructose. The approach uses an iterative design process that exploits the modular structure of folded synthetic oligomer sequences in conjunction with molecular modelling and structural characterization to inform subsequent refinements. Starting from a first-principles design taking size, shape and hydrogen-bonding ability into account and using the high predictability of aromatic oligoamide foldamer conformations and their propensity to crystallize, a sequence that binds to beta-D-fructopyranose in organic solvents with atomic-scale complementarity was obtained in just a few iterative modifications. This scheme, which mimics the adaptable construction of biopolymers from a limited number of monomer units, provides a general protocol for the development of selective receptors.
dc.language.isoen
dc.title.enIterative design of a helically folded aromatic oligoamide sequence for the selective encapsulation of fructose
dc.typeArticle de revue
dc.identifier.doi10.1038/nchem.2195
dc.subject.halChimie/Matériaux
bordeaux.journalNature chemistry
bordeaux.page334-41
bordeaux.volume7
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.issue4
bordeaux.institutionUniversité de Bordeaux
bordeaux.institutionBordeaux INP
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Nature%20chemistry&rft.date=2015&rft.volume=7&rft.issue=4&rft.spage=334-41&rft.epage=334-41&rft.au=CHANDRAMOULI,%20Nagula&FERRAND,%20Yann&LAUTRETTE,%20Guillaume&KAUFFMANN,%20Brice&MACKERETH,%20Cameron%20David&rft.genre=article


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