Selective Encapsulation of Disaccharide Xylobiose by an Aromatic Foldamer Helical Capsule
Xylobiose sequestration in a helical aromatic oligoamide capsule was evidenced by circular dichroism, NMR spectroscopy, and crystallography. The preparation of the 5 kDa oligoamide sequence was made possible by the transient use of acid‐labile dimethoxybenzyl tertiary amide substituents that disrupt...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2018-10, Vol.57 (41), p.13542-13546 |
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| creator | Saha, Subrata Kauffmann, Brice Ferrand, Yann Huc, Ivan |
| description | Xylobiose sequestration in a helical aromatic oligoamide capsule was evidenced by circular dichroism, NMR spectroscopy, and crystallography. The preparation of the 5 kDa oligoamide sequence was made possible by the transient use of acid‐labile dimethoxybenzyl tertiary amide substituents that disrupt helical folding and prevent double helix formation. Binding of other disaccharides was not detected. Crystallographic data revealed a complex composed of a d‐xylobiose α anomer and two water molecules accommodated in the right‐handed helix. The disaccharide was found to adopt an unusual all‐axial compact conformation. A dense network of 18 hydrogen bonds forms between the guest, the cavity wall, and the two water molecules.
A saccharide coiled guest: A foldamer receptor designed from first principles selectively binds and completely wraps a disaccharide. A dense network of 18 hydrogen bonds forms between the guest, the cavity wall, and two water molecules. |
| doi_str_mv | 10.1002/anie.201808370 |
| format | Article |
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A saccharide coiled guest: A foldamer receptor designed from first principles selectively binds and completely wraps a disaccharide. 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| subjects | carbohydrates Chemical Sciences Circular dichroism Conformation Crystallography Dichroism Disaccharides foldamers helical capsules Hydrogen bonding Hydrogen bonds Magnetic resonance spectroscopy Material chemistry molecular recognition NMR spectroscopy Water chemistry |
| title | Selective Encapsulation of Disaccharide Xylobiose by an Aromatic Foldamer Helical Capsule |
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