The meso Helix: Symmetry and Symmetry-Breaking in Dynamic Oligourea Foldamers with Reversible Hydrogen-Bond Polarity
| dc.contributor.author | WECHSEL, Romina | |
| dc.contributor.author | RAFTERY, James | |
| dc.contributor.author | CAVAGNAT, Dominique | |
| dc.contributor.author | GUICHARD, Gilles
IDREF: 084339268 | |
| dc.contributor.author | CLAYDEN, Jonathan | |
| dc.date.accessioned | 2020-09-03T07:56:08Z | |
| dc.date.available | 2020-09-03T07:56:08Z | |
| dc.date.issued | 2016 | |
| dc.identifier.uri | https://oskar-bordeaux.fr/handle/20.500.12278/10828 | |
| dc.description.abstractEn | Oligoureas (up to n=6) of meso cyclohexane-1,2-diamine were synthesized by chain extension with an enzymatically desymmetrized monomer 2. Despite being achiral, the meso oligomers adopt chiral canonical 2.5-helical conformations, the equally populated enantiomeric screw-sense conformers of which are in slow exchange on the NMR timescale, with a barrier to screw-sense inversion of about 70 kJmol(-1) . Screw-sense inversion in these helical foldamers is coupled with cyclohexane ring-flipping, and results in a reversal of the directionality of the hydrogen bonding in the helix. The termini of the meso oligomers are enantiotopic, and desymmetrized analogues of the oligoureas with differentially and enantioselectively protected termini display moderate screw-sense preferences. A screw-sense preference may furthermore be induced in the achiral, meso oligoureas by formation of a 1:1 hydrogen-bonded complex with the carboxylate anion of Boc-d-proline. The meso oligoureas are the first examples of hydrogen-bonded foldamers with reversible hydrogen-bond directionality. | |
| dc.language.iso | en | |
| dc.title.en | The meso Helix: Symmetry and Symmetry-Breaking in Dynamic Oligourea Foldamers with Reversible Hydrogen-Bond Polarity | |
| dc.type | Article de revue | |
| dc.identifier.doi | 10.1002/anie.201604496 | |
| dc.subject.hal | Chimie/Matériaux | |
| bordeaux.journal | Angewandte Chemie (International ed. in English) | |
| bordeaux.page | 9657-61 | |
| bordeaux.volume | 55 | |
| bordeaux.hal.laboratories | Institut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN) - UMR 5248 | * |
| bordeaux.hal.laboratories | Institut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN, UMR 5248) | |
| bordeaux.issue | 33 | |
| bordeaux.institution | Université de Bordeaux | |
| bordeaux.institution | Bordeaux INP | |
| bordeaux.COinS | ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Angewandte%20Chemie%20(International%20ed.%20in%20English)&rft.date=2016&rft.volume=55&rft.issue=33&rft.spage=9657-61&rft.epage=9657-61&rft.au=WECHSEL,%20Romina&RAFTERY,%20James&CAVAGNAT,%20Dominique&GUICHARD,%20Gilles&CLAYDEN,%20Jonathan&rft.genre=article |
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