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Article Dans Une Revue Angewandte Chemie International Edition Année : 2018

Selective Encapsulation of Disaccharide Xylobiose by an Aromatic Foldamer Helical Capsule

Résumé

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 alpha 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.

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Matériaux
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Dates et versions

hal-02536493 , version 1 (08-04-2020)

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Subrata Saha, Brice Kauffmann, Yann Ferrand, Ivan Huc. Selective Encapsulation of Disaccharide Xylobiose by an Aromatic Foldamer Helical Capsule. Angewandte Chemie International Edition, In press, 57 (41), pp.13542-13546. ⟨10.1002/anie.201808370⟩. ⟨hal-02536493⟩

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