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Saha, Subrata; Kauffmann, Brice; Ferrand, Yann; Huc, Ivan (2018): Selective Encapsulation of Disaccharide Xylobiose by an Aromatic Foldamer Helical Capsule. In: Angewandte Chemie-International Edition, Vol. 57, No. 41: pp. 13542-13546
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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 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.